Journal articles: 'Phenanthroline'

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Nycz, Wantulok, Sokolova, Pajchel, Stankevič, Szala, Malecki, and Swoboda. "Synthesis and Electrochemical and Spectroscopic Characterization of 4,7-diamino-1,10-phenanthrolines and Their Precursors." Molecules 24, no. 22 (November 13, 2019): 4102. http://dx.doi.org/10.3390/molecules24224102.

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New approaches to the synthesis of 4,7-dichloro-1,10-phenanthrolines and their corresponding 9H-carbazol-9-yl-, 10H-phenothiazin-10-yl- and pyrrolidin-1-yl derivatives were developed. Their properties have been characterized by a combination of several techniques: MS, HRMS, GC-MS, electronic absorption spectroscopy and multinuclear NMR in both solution and solid state including 15N CP/MAS NMR. The structures of 5-fluoro-2,9-dimethyl-4,7-di(pyrrolidin-1-yl)-1,10-phenanthroline (5d), 4,7-di(9H-carbazol-9-yl)-9-oxo-9,10-dihydro-1,10-phenanthroline-5-carbonitrile (6a) and 4,7-di(10H-phenothiazin-10-yl)-1,10-phenanthroline-5-carbonitrile (6b) were determined by single-crystal X-ray diffraction measurements. The nucleophilic substitutions of hydrogen followed by oxidation produced compounds 6a and 6b. The electrochemical properties of selected 1,10-phenanthrolines were investigated using cyclic voltammetry and compared with commercially available reference 1,10-phenanthrolin-5-amine (5l). The spatial distribution of frontier molecular orbitals of the selected compounds has been calculated by density functional theory (DFT). It was shown that potentials of reduction and oxidation were in consistence with the level of HOMO and LUMO energies.

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Paira, Rupankar, Tarique Anwar, Maitreyee Banerjee, Yogesh P. Bharitkar, Shyamal Mondal, Sandip Kundu, Abhijit Hazra, Prakas R. Maulik, and Nirup B. Mondal. "Copper–phenanthroline catalysts for regioselective synthesis of pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and of pyrrolo[1,2-a]phenanthrolines under mild conditions." Beilstein Journal of Organic Chemistry 10 (March 20, 2014): 692–700. http://dx.doi.org/10.3762/bjoc.10.62.

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A new series of pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and pyrrolo[1,2-a]phenanthrolines were efficiently built up from an 8-hydroxyquinoline derivative or phenanthroline via 1,3-dipolar cycloaddition reaction involving non-stabilized azomethine ylides, generated in situ from the parent furo[3,2-h]quinoliniums/phenanthroliums, in presence of a copper(II) chloride–phenanthroline catalytic system. The methodology combines general applicability with high yields.

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Garypidou, Antonia, Konstantinos Ypsilantis, Evaggelia Sifnaiou, Maria Manthou, Dimitris Thomos, John C. Plakatouras, Theodoros Tsolis, and Achilleas Garoufis. "Synthesis, Characterization and Photophysical Properties of Mixed Ligand (η3-Allyl)palladium(II) Complexes with N,N’Aromatic Diimines." Chemistry 5, no. 4 (November 12, 2023): 2476–89. http://dx.doi.org/10.3390/chemistry5040162.

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Palladium(II) complexes of the general formula [Pd(η3-C3H5)(L)](PF6), where L is 4,7-diphenyl-1,10-phenanthroline (1), 2,9-dimethyl-1,10-phenanthroline (2), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (3), 5-methyl-1,10-phenanthroline (4), 3,4,7,8-tetramethyl-1,10-phenanthroline (5), and 2-(2′-pyridyl) quinoxaline (6), were synthesized and characterized using high-resolution ESI-MS, NMR techniques and, in the case of (6), single-crystal X-ray diffraction methods. In addition, their photophysical properties were investigated. Complexes (1)–(6) were emitted in the greenish-blue region, with those containing methyl-substituted phenanthrolines having the higher quantum yield (≈14%) in the solid state.

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4

Holan, G., and GT Wernert. "The Synthesis of 1,10-Phenanthroline Esters Containing Unsaturated C18 Side Chains." Australian Journal of Chemistry 40, no. 5 (1987): 873. http://dx.doi.org/10.1071/ch9870873.

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Octadeca-6,9,12-trienyl 3,4,7,8-tetramethyl-1,10-phenanthroline-2-carboxylate and 3,7,8-tri-methyl- 1,10-phenanthrolin-4-ylmethyl octadeca-9,12,15-trienoate have been synthesized. Furthermore, two series of 1,10-phenanthroline esters substituted in the 2-position with C18 unsaturated side chains have also been synthesized.

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5

Ustynyuk, Yu A., V. S. Petrov, P. S. Lemport, V. A. Roznyatovsky, and V. G. Nenajdenko. "New Macrocyclic Bis-1,10-phenanthroline-2,9-dicarboxamides. Synthesis and Stereodynamics in Solution." Russian Journal of Organic Chemistry 59, no. 10 (October 2023): 1709–13. http://dx.doi.org/10.1134/s1070428023100056.

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Abstract New macrocyclic 1,10-phenanthroline-2,9-dicarboxamide derivatives containing two phenanthroline cores were synthesized, and their structure was confirmed by NMR spectroscopy and other methods. The new macrocyclic phenanthrolines showed a complex stereodynamic behavior in solution, which was studied by 1H NMR spectroscopy at different temperatures.

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Ustynyuk, Yu A., V. S. Petrov, P. S. Lemport, V. A. Roznyatovsky, and V. G. Nenajdenko. "New macrocyclic bis-1,10-phenanthroline-2,9-diamides. synthesis and stereodynamics in solutions." Журнал органической химии 59, no. 10 (December 15, 2023): 1357–62. http://dx.doi.org/10.31857/s0514749223100063.

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New examples of macrocyclic 1,10-phenanthroline-2,9-diamides containing simultaneously two phenanthroline moiety in their structure have been obtained. The structure of the obtained compounds was confirmed by NMR spectroscopy and other methods. New macrocyclic phenanthrolines expectedly exhibit complex stereodynamic behavior in solutions. This effect was studied using 1H NMR spectroscopy at various temperatures.

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7

Butler, Ian R., and Jean-Louis Roustan. "The synthesis of dipridyl- and 1,10-phenanthrolylferrocenes and bis-N,N′-(2,2′-dipyridyl(6-ferrocenyl-N,N′-2,2′-dipyridyl))ruthenium dichloride." Canadian Journal of Chemistry 68, no. 12 (December 1, 1990): 2212–15. http://dx.doi.org/10.1139/v90-339.

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Ferrocenyldipyridyls and ferrocenyl-o-phenanthrolines have been synthesized by the direct reaction of lithioferrocenes with the appropriate dipyridine or 1,10-phenanthroline. The spectroscopic properties of these potential new ligands are described and the synthesis of bis-2,2′-dipyridyl(6-ferrocenyl-2,2′-dipyridyl)ruthenium dichloride, 8, in its hydrated form is reported. Keywords: ferrocene, dipyridine, phenanthroline, ruthenium.

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8

Levis, Michael, Ulrich Lüning, Michael Müller, Michael Schmittel, and Clemens Wöhrle. "Tris(1,10-phenanthroIine)iron(II) Complexes. Influence of 4,7-Donor Substitution on the Redox Potential [1]." Zeitschrift für Naturforschung B 49, no. 5 (May 1, 1994): 675–82. http://dx.doi.org/10.1515/znb-1994-0519.

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Several new 4.7-donor substituted 1.10-phenanthrolines were synthesized and the corresponding tris(1,10-phenanthroline)iron(II) complexes were studied by cyclic voltammetry. All iron(II) complexes showed fully reversible waves at scan rates between 50 and 500 mV/s. For some redox systems the kinetics in their reaction with chlorine was studied. Complexes 7k and 71 significantly extent the potential range of tris(1,10-phenanthroline)iron(II) complexes.

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9

Krause, Jeanette A., Daoli Zhao, Sayandev Chatterjee, Roland Falcon, Kristen Stoltz, John C. Warren, Sara E. Wiswell, William B. Connick, and Sibrina N. Collins. "In-house and synchrotron X-ray diffraction studies of 2-phenyl-1,10-phenanthroline, protonated salts, complexes with gold(III) and copper(II), and an orthometallation product with palladium(II)." Acta Crystallographica Section C Structural Chemistry 70, no. 3 (February 8, 2014): 260–66. http://dx.doi.org/10.1107/s2053229614001843.

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Different salts of the 2-phenyl-1,10-phenanthrolin-1-ium cation, (pnpH)+, are obtained by reacting 2-phenyl-1,10-phenanthroline (pnp), C18H12N2, (I), with a variety of anions, such as hexafluoridophosphate, C18H13N2+·PF6−, (II), trifluoromethanesulfonate, C18H13N2+·CF3SO3−, (III), tetrachloridoaurate, (C18H13N2)[AuCl4], (IV), and bromide (as the dihydrate), C18H13N2+·Br−·2H2O, (V). Compound (I) crystallizes withZ′ = 2, with both independent molecules adopting a coplanar conformation. In (II)–(IV), a hydrogen bond exists between the cation and anion, while one of the lattice water molecules serves as a hydrogen-bonded bridge between the cation and anion in (V). Reaction of (I) with HAuCl4gives the salt complex (IV); however, reaction with KAuCl4produces the monodentate complex trichlorido(2-phenyl-1,10-phenanthroline-κN10)gold(III), [AuCl3(C18H12N2)], (VI). Dichlorido(2-phenyl-1,10-phenanthroline-κ2N,N′)copper(II), [CuCl2(C18H12N2)], (VII), results from the reaction of CuCl2·2H2O and (I), in which the CuIIcenter adopts a tetrahedrally distorted square-planar geometry. The pendent phenyl ring twists to a bisecting position relative to the phenanthroline plane. The square-planar PdIIcomplex, bromido[2-(phenanthrolin-2-yl)phenyl-κ3C1,N,N′]palladium(II), [PdBr(C18H11N2)], (VIII), is obtained from the reaction of (I) with [PdCl2(cycloocta-1,5-diene)], followed by addition of bromine. A coplanar geometry for the pendent ring is adopted as a result of the tridentate bonding motif.

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10

Al, Matarneh, Catalina Ciobanu, Ionel Mangalagiu, and Ramona Danac. "Design, synthesis and antimycobacterial evaluation of some new azaheterocycles with the 4,7-phenanthroline skeleton. Part VI." Journal of the Serbian Chemical Society 81, no. 2 (2016): 133–40. http://dx.doi.org/10.2298/jsc150514084a.

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A feasible study concerning the synthesis, structure and in vitro antimycobacterial evaluation of new 4,7-phenanthroline derivatives is reported. The preparation is straight and efficient, involving an N-alkylation reaction of 4,7-phenanthroline. The structure of the new compounds have been proved by elemental and spectral (IR, 1H and 13C NMR) analysis. The in vitro antimycobacterial evaluation of five synthesized compounds was investigated against Mycobacterium tuberculosis H37Rv under aerobic conditions. A certain influence of substituents from the para position of the benzoyl moiety was observed, the 4,7-phenanthrolin-4-ium salt substituted with (p)chloro-benzoyl showing the most pronounced antimycobacterial activity.

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11

Nycz, Jacek E., Natalia Martsinovich, Jakub Wantulok, Tieqiao Chen, Maria Książek, and Joachim Kusz. "Synthesis and Spectroscopic Characterization of Selected Water-Soluble Ligands Based on 1,10-Phenanthroline Core." Molecules 29, no. 6 (March 18, 2024): 1341. http://dx.doi.org/10.3390/molecules29061341.

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Water-soluble ligands based on a 1,10-phenanthroline core are relatively poorly studied compounds. Developing efficient and convenient syntheses of them would result in new interesting applications because of the importance of 1,10-phenanthrolines. In this manuscript, we describe novel and practical ways to introduce a carboxyl and, for the first time, a phenol and dithiocarboxyl group under mild reaction conditions. This strategy enables highly efficient and practical synthesis of suitable organosulfur compounds with high added value, high chemoselectivity, and a broad substrate range. We present the selective conversion of a hydroxydialdehyde in the form of 10-hydroxybenzo[h]quinoline-7,9-dicarbaldehyde into its derivative, unique hydroxydicarboxylic acid, by an oxidation procedure, giving 10-hydroxybenzo[h]quinoline-7,9-dicarboxylic acid. A similar procedure resulted in the formation of 9-methyl-1,10-phenanthroline-2-carboxylic acid by oxidation of commercially available neocuproine. An alternative method of obtaining 1,10-phenanthroline derivatives possessing carboxylic acid group can be based on the hydrolysis of ester or nitrile groups; however, this synthesis leads to unexpected products. Moreover, we apply Perkin condensation to synthesize a vinyl (or styryl) analog of 1,10-phenanthroline derivatives with phenol function. This reaction also demonstrates a new, simple, and efficient strategy for converting methyl derivatives of 1,10-phenanthroline. We anticipate that the new way of converting methyl will find wide application in chemical synthesis.

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12

Astakhov, Grigorii, Mikhail Levitsky, Alexander Korlyukov, Lidia Shul’pina, Elena Shubina, Nikolay Ikonnikov, Anna Vologzhanina, et al. "New Cu4Na4- and Cu5-Based Phenylsilsesquioxanes. Synthesis via Complexation with 1,10-Phenanthroline, Structures and High Catalytic Activity in Alkane Oxidations with Peroxides in Acetonitrile." Catalysts 9, no. 9 (August 21, 2019): 701. http://dx.doi.org/10.3390/catal9090701.

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Self-assembly of copper(II)phenylsilsesquioxane assisted by the use of 1,10-phenanthroline (phen) results in isolation of two unusual cage-like compounds: (PhSiO1,5)12(CuO)4(NaO0.5)4(phen)4 1 and (PhSiO1,5)6(PhSiO1,5)7(HO0.5)2(CuO)5(O0.25)2(phen)3 2. X-Ray diffraction study revealed extraordinaire molecular architectures of both products. Namely, complex 1 includes single cyclic (PhSiO1,5)12 silsesquioxane ligand. Four sodium ions of 1 are additionally ligated by 1,10-phenanthrolines. In turn, “sodium-less” complex 2 represents coordination of 1,10-phenanthrolines to copper ions. Two silsesquioxane ligands of 2 are: (i) noncondensed cubane of a rare Si6-type and (ii) unprecedented Si7-based ligand including two HOSiO1.5 fragments. These silanol units were formed due to removal of phenyl groups from silicon atoms, observed in mild conditions. The presence of phenanthroline ligands in products 1 and 2 favored the π–π stacking interactions between neighboring cages. Noticeable that in the case of 1 all four phenanthrolines participated in such supramolecular organization, unlike to complex 2 where one of the three phenanthrolines is not “supramolecularly active”. Complexes 1 and 2 were found to be very efficient precatalysts in oxidations with hydroperoxides. A new method for the determination of the participation of hydroxyl radicals has been developed.

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13

Al-Matarneh, Cristina, Irina Rosca, Sergiu Shova, and Ramona Danac. "Synthesis and properties of new fused pyrrolo-1,10-phenanthroline type derivatives." Journal of the Serbian Chemical Society, no. 00 (2021): 57. http://dx.doi.org/10.2298/jsc200819057a.

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New fused pyrrolo-phenanthroline type derivatives were synthesized, in two steps, from 1,10-phenanthroline and evaluated for antimicrobial activity and fluorescence properties. Our synthetic approach involved a 3+2 dipolar-cycloaddition of some selected N-substituted 1,10-phenanthrolin-1-ium ylides, (m)ethoxycarbonyl and cyano (1,2-di)substituted acetylenes and alkenes, respectively. The structures of compounds were supported by analytical and spectroscopic data. The molecular structures of four selected compounds have also been also determined by monocrystal XRD analyses. All synthesized compounds were then evaluated for their potential antimicrobial activity against Staphylococcus aureus ATCC25923, Escherichia coli ATCC25922 and Candida albicans ATCC10231. Two of the compounds demonstrated significant activity against the above tested strains.

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Devereux, Michael, Malachy McCann, Vanessa Leon, Majella Geraghty, Vickie McKee, and Jan Wikaira. "Synthesis and Biological Activity of Manganese (II) Complexes of Phthalic and Isophthalic Acid: X-Ray Crystal Structures of [Mn(ph)(Phen)2(H2O)]· 4H2O, [Mn(Phen)2(H2O)2]2(Isoph)2(Phen)· 12H2O and {[Mn(Isoph)(bipy)]4· 2.75biby}n(phH2 = Phthalic Acid; isoph = Isophthalic Acid; phen = 1,10-Phenanthroline; bipy = 2,2-Bipyridine)." Metal-Based Drugs 7, no. 5 (January 1, 2000): 275–88. http://dx.doi.org/10.1155/mbd.2000.275.

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Manganese(II) acetate reacts with phthalic acid (phH2) to give [Mn(ph)]·0.5H2O (1). Reaction of 1 with 1,10-phenanthroline produces [Mn(ph)(phen)]·2H2O (2) and [Mn(ph)(phen)2(H2O)]·4H2O (3). Reaction of isophthalic acid (isophH2) with manganese(II) acetate results in the formation of [Mn(isoph)]·2H2O (4). The addition of the N,N-donor ligands 1,10-phenanthroline or 2,2'-bipyridine to 4 leads to the formation of [Mn2 (isoph)2(phen)3)]·4H2O (5), [(Mn(phen)2(H2O)2]2(isoph)2(phen)·12H2O (6) and {[Mn(isoph)(bipy)]4·2.75 biby}n (7), respectively. Molecular structures of 3, 6 and 7 were determined crystallographically. In 3 the phthalate ligand is bound to the manganese via just one of its carboxylate groups in a monodentate mode with the remaining coordination sites filled by four phenanthroline nitrogen and one water oxygen atoms. In 6 the isophthalates are uncoordinated with the octahedral manganese center ligated by two phenanthrolines and two waters. In 7 the Isophthalate ligands act as bridges resulting in a polymeric structure. One of the carboxylate groups is chelating a single manganese with the other binding two metal centres in a bridging bidentate mode. The phthalate and isophthalate complexes, the metal free ligands and a number of simple manganes salts were each tested for their ability, to inhibit the growth of Candida albicans. Only the “metal free” 1,10-phenanthroline and its manganese complexes were found to be active.

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Silva-Caldeira, Priscila Pereira, Antônio Carlos Almendagna de Oliveira Junior, and Elene Cristina Pereira-Maia. "Photocytotoxic Activity of Ruthenium(II) Complexes with Phenanthroline-Hydrazone Ligands." Molecules 26, no. 7 (April 6, 2021): 2084. http://dx.doi.org/10.3390/molecules26072084.

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This paper reports on the synthesis and characterization of two new polypyridyl-hydrazone Schiff bases, (E)-N′-(6-oxo-1,10-phenanthrolin-5(6H)-ylidene)thiophene-2-carbohydrazide (L1) and (E)-N′-(6-oxo-1,10-phenanthrolin-5(6H)-ylidene)furan-2-carbohydrazide (L2), and their two Ru(II) complexes of the general formula [RuCl(DMSO)(phen)(Ln)](PF6). Considering that hydrazides are a structural part of severa l drugs and metal complexes containing phenanthroline derivatives are known to interact with DNA and to exhibit antitumor activity, more potent anticancer agents can be obtained by covalently linking the thiophene acid hydrazide or the furoic acid hydrazide to a 1,10-phenanthroline moiety. These ligands and the Ru(II) complexes were characterized by elemental analyses, electronic, vibrational, 1H NMR, and ESI-MS spectroscopies. Ru is bound to two different N-heterocyclic ligands. One chloride and one S-bonded DMSO in cis-configuration to each other complete the octahedral coordination sphere around the metal ion. The ligands are very effective in inhibiting cellular growth in a chronic myelogenous leukemia cell line, K562. Both complexes are able to interact with DNA and present moderate cytotoxic activity, but 5 min of UV-light exposure increases cytotoxicity by three times.

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Saitoh, Yutaka, Take-aki Koizumi, Kohtaro Osakada, and Takakazu Yamamoto. "Preparation of symmetric dibromides of 1,10-phenanthroline." Canadian Journal of Chemistry 75, no. 10 (October 1, 1997): 1336–39. http://dx.doi.org/10.1139/v97-160.

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Bromation of 1,10-phenanthroline with Br2 proceeds smoothly in the presence of S2Cl2 and pyridine to give 3,8-dibromo-1,10-phenanthroline in good yield. Bromation of 2,9-dibutoxy-1,10-phenanthroline with Br2, in an aqueous medium gives 5,6-dibromo-2,9-dibutoxy-1,10-phenanthroline selectively. Similar bromination of 4,7-dibutoxy-1,10-phenanthroline with Br2 gives 3,8-dibromo-4,7-dibutoxy-1,10-phenanthroline, which forms a 1:1 adduct with Cu(NO3)2. Molecular structure of the 1:1 adduct has been determined by X-ray crystallography. Keywords: bromination, 1,10-phenanthroline, 3,8-dibromo-1,10-phenanthroline.

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Golubeva, Yu A., K. S. Smirnova, L. S. Klyushova, A. S. Berezin, and E. V. Lider. "Cytotoxic Copper(II) Complexes Based on 2,2'-Bipyridine/1,10- Phenanthroline and 5-(4-Chlorophenyl)-1H-tetrazole: Synthesis and Structures." Координационная химия 49, no. 9 (September 1, 2023): 516–29. http://dx.doi.org/10.31857/s0132344x2260062x.

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Five coordination compounds [Cu2(Bipy)2L4]·C2H5OH (Iа, Ib), [Cu2(Dmbipy)2L4] (II),[Cu2(Phen)2L4]·H2O (IIIa), [Cu2(Dmphen)2L4] (IVa), and [Cu2(Phendione’)2L4]·2C2H5OH·2H2O (V) aresynthesized from 5-(4-chlorophenyl)-1H-tetrazole (HL), where Bipy is 2,2'-bipyridine, Dmbipy is 4,4'-dimethyl-2,2'-bipyridine, Phen is 1,10-phenanthroline, Dmphen is 4,7-dimethyl-1,10-phenanthroline, andPhendione’ is 6-ethoxy-6-hydroxy-1,10-phenanthrolin-5-one. The crystal structures of the complexes aredetermined by X-ray diffraction (XRD) of single crystals (CIF files CCDC nos. 2225368 (Ia), 2225369 (Ib),2225370 (II), 2225372 (IIIa), 2225373 (IVa), and 2225371 (V)). The compounds are binuclear due to thebridging function of the tetrazolate anion, and the coordination number of copper is five in all synthesizedcomplexes. The cytotoxic activity of the complexes against the Hep2 and HepG2 cancer cell lines and noncanceroushuman fibroblasts MRC-5 is studied. The complexes exhibit pronounced cytotoxic properties, andcompound V has the maximum selectivity index with respect to the cancer cells.

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Sharrock, Patrick. "Bacteristatic activity of phenanthrolines against Escherichia coli and Bacillus subtilis." Canadian Journal of Microbiology 31, no. 4 (April 1, 1985): 367–70. http://dx.doi.org/10.1139/m85-070.

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Using optical turbidimetry to measure the growth of Escherichia coli and Bacillus subtilis, we determined the mean lethal dose (LD50) values for various phenanthrolines. The dimethyl-substituted compounds are found to be more toxic to bacteria, with doses near 5 μg/mL reducing the number of viable cells by 50% over a 24-h period. 2,9-Dimethyl phenanthroline is the most potent compound against B. subtilis, being six times more effective than against E. coli. Bipyridine is the least toxic substance and is twice as effective against E. coli as it is against B. subtilis. Evidence is presented to show copper ions enhance the antibacterial action of phenanthrolines and may be required for activity.

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DAY, T. A., and G. Z. CHEN. "The metalloprotease inhibitor 1,10-phenanthroline affects Schistosoma mansoni motor activity, egg laying and viability." Parasitology 116, no. 4 (April 1998): 319–25. http://dx.doi.org/10.1017/s0031182097002370.

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The Zn2+-chelating metalloprotease inhibitor 1,10-phenanthroline (phenanthroline, 5–150 μM) elicited dose-dependent contraction of the longitudinal and circular (transverse) musculature of adult male schistosomes. At the same concentrations, phenanthroline did not cause contraction of dispersed individual muscle fibres. The phenanthroline-induced contractions were reduced by the inclusion of 100 or 300 μM Zn2+ in the extracellular medium. Phenanthroline (0·5–150 μM) also inhibited the egg production of adult worm pairs in vitro, with a 98% reduction at 50 μM. When worm pairs were exposed to phenanthroline, the males detached from the dish and released the females, resulting in unpaired worms. At the higher concentrations (50 and 150 μM), the worms were killed in vitro. Worm burdens were reduced by over 50% in infected mice injected with phenanthroline (20 mg/kg/day for 4 days), but twice the dose resulted in only a 25% reduction. Phenanthroline injections also induced an hepatic shift and an unpairing of adult worms in infected mice, and the female worms appeared degenerate and lacked gut pigmentation. Mice fed a diet containing 0·3% phenanthroline received significant protection from infection when challenged with schistosome cercaria, where phenanthroline-fed mice had 94% fewer adult worms than control mice. The broad range of phenanthroline effects on schistosomes suggests broad and important functions for metalloproteases in these worms.

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Ferguson, George, Christopher Glidewell, and Emma S. Lavender. "Crystal engineering using bisphenols and trisphenols. Complexes with 1,10-phenanthroline: hydrogen-bonded chains in adducts with 4,4′-biphenol (1/1) and 4,4′-sulfonyldiphenol (2/3), π–π stacked chains in the (1/2) adduct with 4,4′-thiodiphenol, and pairwise-interwoven nets in 1,1,1-tris(4-hydroxyphenyl)ethane–1,10-phenanthroline–methanol (1/1/1)." Acta Crystallographica Section B Structural Science 55, no. 4 (August 1, 1999): 591–600. http://dx.doi.org/10.1107/s0108768199002657.

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In 4,4′-biphenol–1,10-phenanthroline (1/1) [systematic name: 4,4′-biphenyldiol–1,10-phenanthroline (1/1)] the diphenol molecules lie across centres of inversion and the phenanthroline molecules lie across twofold rotation axes; the phenanthroline molecules act as chain-building units and the molecular components are linked into steeply zigzag C(16) chains parallel to [101] by means of O—H...N hydrogen bonds. In the structure of 4,4′-thiodiphenol–1,10-phenanthroline (1/2) the phenanthroline molecules act as chain-terminating units; the supramolecular aggregation is finite, with the bisphenol linked to each phenanthroline molecule by means of a single O—H...N hydrogen bond. π−π stacking interactions between the phenanthroline molecules in neighbouring hydrogen-bonded aggregates serve to link these aggregates into a continuous two-dimensional array. The phenanthroline molecules in 4,4′-sulfonyldiphenol–1,10-phenanthroline (2/3) play two roles: molecules in general positions act as chain-terminating units and are linked to the sulfonyldiphenol molecules by means of three-centre O—H...(N)2 hydrogen bonds, while those lying across twofold rotation axes act as chain builders and are linked to two different sulfonyldiphenol molecules by means of a two-centre O—H...N hydrogen bond in each case; the resulting U-shaped five-component aggregates are further linked by C—H...O=S hydrogen bonds into a C_3^3(17)[R_2^2(12)] `chain of rings' along [001]. In 1,1,1-tris(4-hydroxyphenyl)ethane–1,10-phenanthroline–methanol (1/1/1) [systematic name: 4,4′,4′′-ethylidynetriphenol–1,10-phenanthroline–methanol (1/1/1)] the phenanthroline molecules again act as chain-terminating units: the trisphenol molecules and the methanol molecules are linked by O—H...O hydrogen bonds into two-dimensional nets built from R_6^6(42) rings, and pairs of these nets are interwoven. The formation of each net utilizes two hydroxyl groups per trisphenol molecule as hydrogen-bond donors and the remaining hydroxyl group acts as donor to the phenanthroline molecule in a three-centre O—H...(N)2 hydrogenbond.

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21

Bauer, Matthias, Maike Tünnermann, Pia Rehsies, and Ulrich Flörke. "A Straightforward Synthesis to Novel 1,10-Phenanthrolines with Fused Thiophene Structure." Synlett 29, no. 20 (October 24, 2018): 2638–42. http://dx.doi.org/10.1055/s-0037-1611022.

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We report here a straightforward synthesis for a series of new structures with fused 1,10-phenanthroline-thiophene connection. They are synthesized with a modified Hinsberg thiophene procedure, followed by successive modification to yield several 5,7-disubstituted thieno[3,4-f][1,10]phenanthrolines, most notable thiophene-substituted compounds that could be potentially of use for organic electronics applications. For some selected examples, crystal structures were obtained, showing a nearly coplanar arrangement around the fused connection, also beneficial for an effective electron transfer in organic electronics or solar cells.

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22

Pakulski, Paweł, Mirosław Arczyński, and Dawid Pinkowicz. "Bis(triphenylphosphine)iminium Salts of Dioxothiadiazole Radical Anions: Preparation, Crystal Structures, and Magnetic Properties." Crystals 9, no. 1 (January 7, 2019): 30. http://dx.doi.org/10.3390/cryst9010030.

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Phenanthroline dioxothiadiazoles are redox active molecules that form stable radical anions suitable for the construction of supramolecular magnetic materials. Herein, the preparation, structures and magnetic properties of bis(triphenylphosphine)iminium (PPN) salts of [1,2,5]thiadiazole[3,4-f][1,10]phenanthroline 1,1-dioxide (L), [1,2,5]thiadiazole[3,4-f][4,7]phenanthroline 1,1-dioxide (4,7-L), 5-bromo-[1,2,5]thiadiazolo[3,4-f][1,10]phenanthroline 2,2-dioxide (BrL), and 5,10-dibromo-[1,2,5]thiadiazolo[3,4-f][1,10]phenanthroline 2,2-dioxide (diBrL) are reported. The preparation of new bromo derivatives of the L: 5-bromo-[1,2,5]thiadiazolo[3,4-f][1,10]phenanthroline 2,2-dioxide (BrL) and 5,10-dibromo-[1,2,5]thiadiazolo[3,4-f][1,10]phenanthroline 2,2-dioxide (diBrL)—suitable starting materials for further derivatization—are described starting from a commercially available and cheap 1,10-phenanthroline. All PPN salts show antiferromagnetic interactions between the pairs of radical anions, which in the case of PPN(diBrL) are very strong (−116 cm−1; using Ĥ = −2JSS type of exchange coupling Hamiltonian) due to a different crystal packing of the anion radicals as compared to PPN(L), PPN(4,7-L), and PPN(BrL).

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23

Krause-Heuer, Anwen M., Peter Leverett, Albert Bolhuis, and Janice R. Aldrich-Wright. "Copper(II) and Palladium(II) Complexes with Cytotoxic and Antibacterial Activity." Australian Journal of Chemistry 65, no. 7 (2012): 860. http://dx.doi.org/10.1071/ch12058.

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The synthesis of eight square pyramidal copper complexes with general structure [Cu(IL)(AL)H2O]2+, where IL represents various methylated 1,10-phenanthrolines, and AL represents either 1S,2S- or 1R,2R-diaminocyclohexane, is reported, with the complexes synthesised as both the perchlorate and chloride salts. The crystal structures of [Cu(1,10-phenanthroline)(1S,2S-diaminocyclohexane](ClO4)2·H2O and [Cu(5,6-dimethyl-1,10-phenanthroline)(1S,2S-diaminocyclohexane](ClO4)2·1.5H2O are reported. Four square planar palladium complexes with general structure [Pd(IL)(AL)]Cl2 have also been synthesised. These complexes were synthesised in order to investigate the structure–activity relationship against both cancer cell lines and bacterial cultures. The copper complexes display anticancer activity similar to cisplatin and 1,10-phenanthroline (phen) in the L1210 murine leukaemia cell line. Methylation of the phen increased the copper complex cytotoxicity by approximately four-fold, compared with the non-methylated complex. No significant difference in activity was observed by altering the chirality of the diaminocyclohexane ligand. The copper complexes demonstrated antibacterial activity against Bacillus subtilis, Staphylococcus aureus, and Escherichia coli; however, high levels of toxicity (30–60 % of death) were observed in the nematode Caenorhabditis elegans. The copper complexes have also been shown to act as DNA nucleases, with the ability to cleave plasmid DNA in the presence of hydrogen peroxide. The palladium complexes all have half maximal inhibitory concentration (IC50) values of ~10 μM in the L1210 cell line, with no significant difference in the cytotoxicity of any of the compounds tested. Minimal antibacterial activity of the palladium complexes was observed.

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24

Výprachtický, Drahomír, Dana Kaňková, Veronika Pokorná, Ivan Kmínek, Vagif Dzhabarov, and Věra Cimrová. "Novel and Simple Synthesis of Brominated 1,10-Phenanthrolines." Australian Journal of Chemistry 67, no. 6 (2014): 915. http://dx.doi.org/10.1071/ch13711.

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A novel, simple, and reasonably efficient synthesis of 3,8-dibromo-1,10-phenanthroline, 3,6-dibromo-1,10-phenanthroline, 3,5,8-tribromo-1,10-phenanthroline, and 3,5,6,8-tetrabromo-1,10-phenanthroline is presented herein. The crucial role of a new catalyst (sulfur dichloride – SCl2) for the bromination of 1,10-phenanthroline is reported. The bromination of 1,10-phenanthroline monohydrate in the presence of SCl2 and pyridine yielded the brominated compounds, previously only possible through the complicated multi-step and tedious Skraup synthesis method. The application of the bromination catalyst SCl2 as a medium-strength Lewis acid is demonstrated for the first time, and the results are compared with the behaviours of known weak (sulfur chloride – S2Cl2) and strong (thionyl chloride – SOCl2) bromination catalysts. A reaction mechanism was proposed.

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25

Bond, Andrew D., Ning Shan, and William Jones. "4,7-Phenanthroline." Acta Crystallographica Section E Structure Reports Online 57, no. 2 (January 30, 2001): o145—o146. http://dx.doi.org/10.1107/s1600536801000812.

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26

James, Marisa, Madelyn R. Shevlin, Thomas B. Green, Megan M. Smart, Colin D. McMillen, and Jared A. Pienkos. "Crystal Structures of DNA Intercalating Agents Dipyrido[3,2-f:2′,3′-h]quinoxaline (dpq), (Benzo[i]dipyrido[3,2-a:2′,3′c]phenazine (dppn), and [Ir(ppy)2(dppn)][PF6] (Where Hppy = 2-Phenylpyridine)." Inorganics 11, no. 9 (August 29, 2023): 353. http://dx.doi.org/10.3390/inorganics11090353.

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Pyrazino-phenanthroline ligands are commonly used with transition metals as DNA intercalation agents. Herein, we report the characterization of two commonly utilized pyrazino-phenanthroline ligands, dipyrido[3,2-f:2′,3′-h]quinoxaline (dpq) and (benzo[i]dipyrido[3,2-a:2′,3′c]phenazine (dppn), by single-crystal X-ray diffraction. Additionally, the characterization of [Ir(ppy)2(dppn)][PF6], where Hppy = 2-phenylpyridine, by single-crystal X-ray diffraction is described. Both the dpq and dppn ligands crystallize as chloroform solvates where the chloroform molecule occupies the equivalent binding pocket of a metal in metal complexes of these ligands. These pyrazino-phenanthrolines are largely planar, with the dppn ligand displaying a slight twist. When the dppn ligand is coordinated to iridium(III), the dppn ligand on the resulting complex displays a significant degree of bending along the longitudinal direction of the ligand. This iridium (III) complex crystallizes as a CH2Cl2 and Et2O solvate and due to the volatility of these solvents these crystals are only stable for a few seconds outside of the mother liquor. The structures of the free ligands and the [Ir(ppy)2(dppn)][PF6] complex all display extensive π stacking interactions.

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27

Yang, Weixi, and Tamaki Nakano. "Synthesis of poly(1,10-phenanthroline-5,6-diyl)s having a π-stacked, helical conformation." Chemical Communications 51, no. 97 (2015): 17269–72. http://dx.doi.org/10.1039/c5cc07005h.

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5,6-Dibromo-1,10-phenanthroline and 2,9-di-n-butyl-5,6-dibromo-1,10-phenanthroline were polymerized using a Ni catalyst to afford helical polymers in which the phenanthroline moieties are densely stacked on top of each other.

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28

Schoffers, Elke, Son Duc Tran, and Kristen Mace. "Preparation of Chiral 5,6-trans-Disubstituted Phenanthrolines from Phenanthroline-5,6-epoxide." HETEROCYCLES 60, no. 4 (2003): 769. http://dx.doi.org/10.3987/com-02-9689.

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29

Hensen, K., F. Gebhardt, and M. Bolte. "1,10-Phenanthrolin-1-ium Chloride Bis(1,10-phenanthroline) Solvate at 143K." Acta Crystallographica Section C Crystal Structure Communications 54, no. 3 (March 15, 1998): 359–61. http://dx.doi.org/10.1107/s0108270197016363.

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30

Li, Feng, Han-Dong Yin, Jun Zhai, and Da-Qi Wang. "1,10-Phenanthrolinium tetraiodo(1,10-phenanthroline-κ2 N,N′)bismuthate(III) 1,10-phenanthroline." Acta Crystallographica Section E Structure Reports Online 62, no. 5 (April 29, 2006): m1170—m1172. http://dx.doi.org/10.1107/s1600536806014991.

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The asymmetric unit of the title compound, (C12H9N2)[BiI4(C12H8N2)]·C12H8N2, comprises a 1,10-phenanthrolinium cation and a tetraiodo(1,10-phenanthroline)bismuthate(III) anion, together with a neutral 1,10-phenanthroline molecule. The BiIII ion adopts a distorted octahedral coordination geometry, binding to the two N atoms of a chelating 1,10-phenanthroline ligand and four iodide ions. N—H...N and C—H...I hydrogen bonding between the 1,10-phenanthroline molecule, the 1,10-phenanthrolinium cation and the BiIII complex cation stabilize the crystal structure.

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31

Carver, J. A., G. S. Baldwin, D. B. Keech, R. Bais, and J. C. Wallace. "Inactivation of chicken liver pyruvate carboxylase by 1,10-phenanthroline." Biochemical Journal 252, no. 2 (June 1, 1988): 501–7. http://dx.doi.org/10.1042/bj2520501.

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Inactivation of chicken liver pyruvate carboxylase by the chelating agent 1,10-phenanthroline follows pseudo-first-order kinetics. The hyperbolic dependence of the apparent first-order rate constant on 1,10-phenanthroline concentration is consistent with a two-step inactivation mechanism, in which 1,10-phenanthroline binds firstly to the enzyme, and secondly to the enzyme-bound Mn(II) ion. Binding of 1,10-phenanthroline to pyruvate carboxylase results in complete loss of ATP/Pi exchange activity, but only a 61% decrease in pyruvate/oxaloacetate exchange activity. The rate of inactivation is greater at low enzyme concentrations, implying that binding of 1,10-phenanthroline to monomers and dimers is preferred relative to that of tetramers. Furthermore, in the presence of acetyl-CoA, which stabilizes the tetrameric structure, no dependence of inactivation on enzyme concentration is observed. As monitored by gel-permeation liquid chromatography, formation of the enzyme-Mn(II)-phenanthroline complex results in loss of the tetrameric structure of the enzyme. From atomic-absorption measurements, inactivation by 1,10-phenanthroline also causes some loss of Mn(II) from the enzyme. It is concluded that the Mn(II) atom does not participate directly in the reaction mechanism, but may play a structural role essential to the integrity of the enzyme's tetrameric structure.

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32

Liu, Hai-Xing, Gui-Ying Dong, Zhi-Hong Ma, and Guang-Hua Cui. "Diaquabis(1,10-phenanthroline)magnesium dichromate(VI) 1,10-phenanthroline disolvate." Acta Crystallographica Section E Structure Reports Online 65, no. 9 (August 8, 2009): m1026. http://dx.doi.org/10.1107/s1600536809030128.

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33

Guillon, Jean, Anita Cohen, Clotilde Boudot, Sarah Monic, Solène Savrimoutou, Stéphane Moreau, Sandra Albenque-Rubio, et al. "Design, Synthesis, and Antiprotozoal Evaluation of New Promising 2,9-Bis[(substituted-aminomethyl)]-4,7-phenyl-1,10-phenanthroline Derivatives, a Potential Alternative Scaffold to Drug Efflux." Pathogens 11, no. 11 (November 13, 2022): 1339. http://dx.doi.org/10.3390/pathogens11111339.

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A series of novel 2,9-bis[(substituted-aminomethyl)]-4,7-phenyl-1,10-phenanthroline derivatives was designed, synthesized, and evaluated in vitro against three protozoan parasites (Plasmodium falciparum, Leishmania donovani and Trypanosoma brucei brucei). Pharmacological results showed antiprotozoal activity with IC50 values in the sub and μM range. In addition, the in vitro cytotoxicity of these original molecules was assessed with human HepG2 cells. The substituted diphenylphenanthroline 1l was identified as the most potent antimalarial derivative with a ratio of cytotoxic to antiparasitic activities of 505.7 against the P. falciparum CQ-resistant strain W2. Against the promastigote forms of L. donovani, the phenanthrolines 1h, 1j, 1n and 1o were the most active with IC50 from 2.52 to 4.50 μM. The phenanthroline derivative 1o was also identified as the most potent trypanosomal candidate with a selectivity index (SI) of 91 on T. brucei brucei strain. FRET melting and native mass spectrometry experiments evidenced that the nitrogen heterocyclic derivatives bind the telomeric G-quadruplexes of P. falciparum and Trypanosoma. Moreover, as the telomeres of the parasites P. falciparum and Trypanosoma could be considered to be possible targets of this kind of nitrogen heterocyclic derivatives, their potential ability to stabilize the parasitic telomeric G-quadruplexes have been determined through the FRET melting assay and by native mass spectrometry.

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34

Zhong, Kai-Long, and Chao Ni. "Bis(6-nitro-1,10-phenanthrolin-1-ium) 2,5-dicarboxyterephthalate." Acta Crystallographica Section E Structure Reports Online 70, no. 3 (February 8, 2014): o256—o257. http://dx.doi.org/10.1107/s1600536814002414.

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In the structure of the title 2:1 proton-transfer compound, 2C12H8N3O2+·C10H4O82−, the 6-nitro-1,10-phenanthroline molecules act as proton sponges, accepting protons from pyromellitic acid. The –NO2group of one of the 6-nitro-1,10-phenanthrolin-1-ium cations is disordered and was refined with a site-occupancy ratio of 0.624 (15):0.376 (15). Two –COOH(–COO−) groups of the 2,5-dicarboxyterephthalate dianion are disordered and were refined with site-occupancy ratios of 0.769 (4):0.231 (4) and 0.766 (5):0.234 (5). The –NO2group of the second cation is also disordered about a pseudo-twofold rotation axis and was refined with a site-occupancy ratio of 0.903 (3):0.097 (3). There is an intramolecular O—H...O hydrogen bond in the anion. The phenanthroline rings of the two cations are inclined to one another by 31.3 (1)°. In the anions, considering the major components only, the carboxylic acid groups (–COOH) are inclined to the benzene ring by 17.3 (2) and 22.3 (3)°. The carboxylate groups (–COO−) are twisted by 9.3 (2) and 13.6 (6)° with respect to the benzene ring. In the crystal, adjacent 2,5-dicarboxyterephthalate anions are linkedviaO—H...O hydrogen bonds, forming chains propagating along [010]. The cations are attached to the chain of anions by N—H...O hydrogen bonds.

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35

Nocton, Grégory, and Louis Ricard. "Reversible C–C coupling in phenanthroline complexes of divalent samarium and thulium." Chemical Communications 51, no. 17 (2015): 3578–81. http://dx.doi.org/10.1039/c5cc00289c.

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36

Najóczki, Ferenc, Mária Szabó, Norbert Lihi, Antal Udvardy, and István Fábián. "Synthesis and Characterization of 1,10-Phenanthroline-mono-N-oxides." Molecules 26, no. 12 (June 14, 2021): 3632. http://dx.doi.org/10.3390/molecules26123632.

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N-oxides of N-heteroaromatic compounds find widespread applications in various fields of chemistry. Although the strictly planar aromatic structure of 1,10-phenanthroline (phen) is expected to induce unique features of the corresponding N-oxides, so far the potential of these compounds has not been explored. In fact, appropriate procedure has not been reported for synthesizing these derivatives of phen. Now, we provide a straightforward method for the synthesis of a series of mono-N-oxides of 1,10-phenanthrolines. The parent compounds were oxidized by a green oxidant, peroxomonosulfate ion in acidic aqueous solution. The products were obtained in high quality and at good to excellent yields. A systematic study reveals a clear-cut correlation between the basicity of the compounds and the electronic effects of the substituents on the aromatic ring. The UV spectra of these compounds were predicted by DFT calculations at the TD-DFT/TPSSh/def2-TZVP level of theory.

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37

Hill, Walter E., Douglas J. Bucklin, James M. Bullard, Alana L. Galbraith, Narasimham V. Jammi, Charles C. Rettberg, Brennan S. Sawyer, and Michael A. Van Waes. "Identification of ribosome–ligand interactions using cleavage reagents." Biochemistry and Cell Biology 73, no. 11-12 (December 1, 1995): 1033–39. http://dx.doi.org/10.1139/o95-110.

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To characterize ribosome–ligand interactions, we have used a cleavage reagent, 1,10-orthopenanthroline–Cu(II), tethered to various ligands, to cleave nearby regions of rRNA. The phenanthroline is tethered to the ligand using either an internal 4-thiouridine or a terminal thiophosphate. When Cu2+ and a reducing agent, such as mercaptopropionic acid, are present, cleavage of nearby nucleic acids occurs. The cleavage sites can be identified using primer-extension analysis. We have identified rRNA cleavage sites resulting from transcribed tRNAPhe having randomly placed phenanthroline–Cu(II), tRNAPhe with phenanthroline–Cu(II) at position 8, and a DNA oligomer complementary to positions 2655–2667 (α-sarcin region) with phenanthroline–Cu(II) placed at the 5′ end. These results provide important new information on the structure of the rRNA within ribosomal subunits and on the proximity of rRNA neighborhoods to these bound ligands.Key words: ribosomal RNA structure, cleavage, phenanthroline, tRNA interactions, ribosome structure.

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38

Fernandes, José A., Olufunso Abosede, and Simona Galli. "Powder X-ray diffraction structural characterization of the coordination complex cis-[Co(κ2N,N′-1,10-phenanthroline-5,6-dione)2Cl2]." Powder Diffraction 33, no. 1 (February 19, 2018): 55–61. http://dx.doi.org/10.1017/s0885715618000143.

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The reduction of cis-[CoIII(κ2N,N′-1,10-phenanthroline-5,6-dione)2Cl2]Cl into the neutral compound cis-[CoII(κ2N,N′-1,10-phenanthroline-5,6-dione)2Cl2] was observed during developmental studies of new antimalarial drugs. The crystal structure of cis-[CoII(κ2N,N′-1,10-phenanthroline-5,6-dione)2Cl2] was unveiled by powder X-ray diffraction studies (PXRD). PXRD details, unit cell parameters, and space group for cis-[CoII(κ2N,N′-1,10-phenanthroline-5,6-dione)2Cl2], C24H12Cl2CoN4O4, are reported [a = 41.4951 (13) Å, b = 8.2768 (2) Å, c = 12.4994 (3) Å, unit cell volume V = 4292.9 (2) Å3, Z = 8, and space group Fdd2]. Infrared spectroscopy features are also discussed.

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39

Hadanu, Ruslin, Sabirin Mastjeh, Jumina Jumina, Mustofa Mustofa, Mahardika Agus Widjayanti, and Eti Nurwening Sholikhah. "SYNTHESIS AND ANTIPLASMODIAL ACTIVITY TESTING OF (1)-N-(4-METHOXYBENZYL)-1,10-PHENANTHROLINIUM BROMIDE." Indonesian Journal of Chemistry 7, no. 2 (June 20, 2010): 197–201. http://dx.doi.org/10.22146/ijc.21698.

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Synthesis of (1)-N-(4-methoxybenzyl)-1,10-phenanthroline bromide from 1,10-phenanthroline monohydrate and 4-methoxybenzaldehyde as starting material and evaluation of its antiplasmodial activities have been carried out. The 4-methoxybenzyl alcohol was prepared from 4-methoxy-benzaldehyde using sodium borohydride (NaBH4) reagent and ethanol absolute solution. The mixture was refluxed for 3 h. To yield colorless dilution compound with 90.41 % in efficiency. Furthermore, bromination of 4-methoxybenzyl alcohol with phosphorus bromide (PBr3) was conducted by refluxing for 3 h. The product of this reaction was yellow liquid of 4-methoxybenzyl bromide, 79.03% yield and 95.34 % purity. The final step of reaction was benzylation of 1,10-phenanthroline monohydrate with 4-methoxybenzyl bromide reagent. It was conducted by refluxing in aceton for 8 h at 55 oC. The yield of the reaction was (1)-N-(4-methoxybenzyl)-1,10-phenanthroline bromide (77.63%). It is pink solid form, and its melting point is 192-193 oC. Identification of the product was carried out by means of GC-MS, IR and 1H-NMR spectrometers. The in vitro antiplasmodial activity on chloroquine-resistant Plasmodium falciparum FCR-3 strain and chloroquine sensitive P. falciparum D10 strain for (1)-N-(4-methoxybenzyl)-1,10-phenanthroline bromide were determined by microscopic method. The result showed that after 72 h incubation, it has IC50 0.93±0.02 µM and 1.21±0.09 µM, respectively. Keywords: 1,10-phenanthroline, (1)-N-(4-methoxybenzyl)-1,10-phenanthroline bromide, 4 methoxybenzaldehyde, antiplasmodial activities

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40

Cusumano, Matteo, Maria Letizia Di Pietro, and Antonino Giannetto. "DNA Interaction of Platinum(II) Complexes with 1,10-Phenanthroline and Extended Phenanthrolines." Inorganic Chemistry 45, no. 1 (January 2006): 230–35. http://dx.doi.org/10.1021/ic050880o.

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41

Hadanu, Ruslin, Mustofa Mustofa, and Nazudin Nazudin. "Synthesis and Antimalarial Activity of 2-Phenyl-1,10-Phenanthroline Derivative Compounds." Jurnal Natur Indonesia 15, no. 1 (July 14, 2014): 57. http://dx.doi.org/10.31258/jnat.15.1.57-62.

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To develop new potential antimalarial drugs of 2-phenyl-1,10-phenanthroline 5 derivatives from 8-aminoquinoline as startingmaterial were synthesized in good yields. The synthesis of 2-phenyl-1,10-phenanthroline 5 derivatives compoundswith 8-aminoquinoline 4 as starting material through three steps has been carried out. The first step of reactions is aldolcondensation of benzaldehyde 1 with acetaldehyde 2. The result of reactions is cinnamaldehyde 3 (92.14%) in the form ofyellow solid. The second step of reactions was synthesized of 2-phenyl-1,10-phenanthroline 5 (brown solid, 54.63%)through cyclization of 8-aminoquinoline 4 with cinnamaldehyde 3 compound. The third step of reactions is methylation andethylation of 2-phenyl-1,10-phenanthroline using dimethyl sulphate (DMS) and diethyl sulphate (DES) reagents that it wasrefluxed for 17 and 19 h, respectively. The results of reactions are (1)-N-methyl-9-phenyl-1,10-phenanthrolinium sulphate 6and (1)-N-ethyl-9-phenyl-1,10-phenanthrolinium sulphate 7 in yield from 90.62% and 89.70%, respectively. The results oftesting in vitro antiplasmodial activity at chloroquine-resistant Plasmodium falciparum FCR3 strain to 2-phenyl-1,10-phenanthroline 5 derivatives obtained that (1)-N-ethyl-9-phenyl-1,10-phenanthrolinium sulphate 7 compound has higherantimalarial activity (IC 50 :0.13 ± 0.02 μM) than antimalarial activity of (1)-N-methyl-9-phenyl-1,10-phenanthrolinium sulphate6 compound (IC 50 :0.25 ± 0.01 μM) and 2-phenyl-1,10-phenanthroline 5 compound (IC 50 :2.45 ± 0.09 μM). While, the resultsof testing in vitro antiplasmodial activity at chloroquine-resistant Plasmodium falciparum D10 strain to 2-phenyl-1,10-phenanthroline 5 derivatives obtained that (1)-N-methyl-9-phenyl-1,10-phenanthrolinium sulphate 6 compound has higherantimalarial activity (IC 50 :0.10± 0.04 μM) than antimalarial activity of (1)-N-ethyl-9-phenyl-1,10-phenanthrolinium sulphate7 (IC 50 :0.18 ± 0.01 μM) and 2-phenyl-1,10-phenanthroline 5 compound (IC 50 :0.55 ± 0.07 μM).

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42

Nejatipour, Hajar, and Mehrdad Dadsetani. "First principles study of the structural, electronic and optical properties of crystalline o-phenanthroline." International Journal of Modern Physics B 30, no. 14 (June 2, 2016): 1650077. http://dx.doi.org/10.1142/s0217979216500776.

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In a comprehensive study, structural properties, electronic structure and optical response of crystalline o-phenanthroline were investigated. Our results show that in generalized gradient approximation (GGA) approximation, o-phenanthroline is a direct bandgap semiconductor of 2.60 eV. In the framework of many-body approach, by solving the Bethe–Salpeter equation (BSE), dielectric properties of crystalline o-phenanthroline were studied and compared with phenanthrene. Highly anisotropic components of the imaginary part of the macroscopic dielectric function in o-phenanthroline show four main excitonic features in the bandgap region. In comparison to phenanthrene, these excitons occur at lower energies. Due to smaller bond lengths originated from the polarity nature of bonds in presence of nitrogen atoms, denser packing, and therefore, a weaker screening effect, exciton binding energies in o-phenanthroline were found to be larger than those in phenanthrene. Our results showed that in comparison to the independent-particle picture, excitonic effects highly redistribute the oscillator strength.

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43

Shahroosvand, Hashem, Parisa Abbasi, Behrouz Notash, and Leyla Najafi. "Separation of Functionalized 5,6-Disubstituted-1,10-Phenanthroline for Dye-Sensitized Solar Cell Applications." Journal of Chemistry 2013 (2013): 1–8. http://dx.doi.org/10.1155/2013/475843.

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5,6-Epoxy-1,10-phenanthroline is used as a convenient starting material for 5-hydroxy-6-Aryl-1,10-phenanthroline ligands containing carboxylic and sulfonic groups useful for further anchoring of the sensitizer on TiO2for dye-sensitized solar cells (DSCs). Based on the crystal growth of the mixture of products, a convenient separation route for the extension of the p-system on 5,6-disubstituted-1,10-phenanthroline was used to develop a novel series of functionalized 1,10-phenanthroline ligands with electron-withdrawing end-capping group. Also, we report the epoxy opening of 5,6-epoxy-1,10-phenanthroline by aromatic amines stoichiometrically in refluxing water and ethanol in the absence of any catalyst. The dyes were characterized by1H-NMR, FT-IR, UV-Vis, and X-ray single crystal diffraction analyses. It crystallizes in the monoclinic space groupC 2/c,a= 20.920(4) Å,b= 10.340(2) Å,c= 16.187(3) Å,β= 92.30(3)°,V= 3498.6(12) Å3, andZ= 8. The reaction details and features were described in detail.

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44

Wang, Z. X., H. B. Wu, X. C. Wang, H. M. Zhou, and C. L. Tsou. "Kinetics of the course of inactivation of aminoacylase by 1,10-phenanthroline." Biochemical Journal 281, no. 1 (January 1, 1992): 285–90. http://dx.doi.org/10.1042/bj2810285.

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The kinetic theory of the substrate reaction during modification of enzyme activity previously described [Tsou (1988) Adv. Enzymol. Relat. Areas Mol. Biol. 61, 381-436] has been applied to a study on the kinetics of the course of inactivation of aminoacylase by 1,10-phenanthroline. Upon dilution of the enzyme that had been incubated with 1,10-phenanthroline into the reaction mixture, the activity of the inhibited enzyme gradually increased, indicating dissociation of a reversible enzyme–1,10-phenanthroline complex. The kinetics of the substrate reaction with different concentrations of the substrate chloroacetyl-L-alanine and the inactivator suggest a complexing mechanism for inactivation by, and substrate competition with, 1,10-phenanthroline at the active site. The inactivation kinetics are single phasic, showing that the initial formation of an enzyme-Zn(2+)-1,10-phenanthroline complex is a relatively rapid reaction, followed by a slow inactivation step that probably involves a conformational change of the enzyme. The presence of Zn2+ apparently stabilizes an active-site conformation required for enzyme activity.

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45

Sun, Jing, Wen-Xiu Chen, Xing-Dong Song, Shu-Fen He, Jia-Xi Chen, Jun Mei, Xiao-Xian Zhu, and Tie Wu. "Synthesis, Characterization, and Inducing Tumor Cell Apoptosis of Two Ru(II) Complexes Containing Guanidinium as Ligands." Anti-Cancer Agents in Medicinal Chemistry 18, no. 1 (March 16, 2018): 110–20. http://dx.doi.org/10.2174/1871520617666170419122056.

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Description: Two new ruthenium(II) complexes containing guanidinium as ligands, [Ru(dip)2 (L1)]3+ (Ru1) and [Ru(dip)2(L2)]3+ (Ru2) (dip=4,7-diphenyl-1,10-phenanthroline; L1=1-(4-(1H-imidazo[4,5- f][1,10]phenanthrolin-2-yl)phenyl)guanidine cation; L2 = 1-(3-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl) phenyl)guanidine cation) have been synthesized and characterized. Both complexes display higher cytotoxicity against several cancer cell lines compared to cisplatin and are less cytotoxic on the nontumorigenic cell line LO2. Intracellular distribution studies show that these complexes are selectively localized in the cytoplasm. Findings: Further analysis revealed that Ru1 and Ru2 had no obvious effects on the cell cycle and induced apoptosis in HeLa cells via the mitochondrial pathway, which involved reactive oxygen species (ROS) accumulation, mitochondrial dysfunction, and Bcl-2 family member activation. Taken together, the two complexes have the potential to be utilized as anticancer agents.

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46

Feng, Liang Dong, Bo Qing Chen, Ying Ying Shi, Ying Wei Guo, Jing Huang, Man Sun, Ya Xin Gu, and Deng Hao Li. "Adsorption Characters of Mn²⁺ onto Palygorskites Modified by 1, 10-Phenanthroline and Triethylamine." Advanced Materials Research 178 (December 2010): 8–16. http://dx.doi.org/10.4028/www.scientific.net/amr.178.8.

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1, 10-phenanthroline and triethylamine modified palygorskites were prepared by microwave irradiation, and characterized with FT-IR technique. The effects of contact time, adsorbent dosage, and pH value of the initial solution on the adsorption characters of Mn2+ were investigated. The adsorption of Mn2+ from aqueous solutions using 1, 10-phenanthroline or triethylamine modified palygorskites were investigated. Experiment results indicated that 1,10-phenanthroline and triethylamine molecules have been successfully grafted to palygorskite. The adsorption was rapid during the ﬁrst 5 minuts and equilibrium were attained within 60 minutes in the initial concentration of Mn2+ of 50 and 100 mg•L-1, and fast adsorption in the first 10 minutes and slowly increased with the contact time due to the adsorption of palygorskite. The 1, 10-phenanthroline modified palygorskites had higher adsorption capacity than triethylamine modified palygorskites. Compared with natural palggorskites, the Mn2+ ions adsorption capacities of palggorskite modified by 1, 10-phenanthroline or triethylamine were significantly improved. There were less difference in the adsorption capacity between different dasages of 1, 10-phenanthroline modified palygorskites, but the adsorption capacity of Mn2+ adsorbed onto triethylamine modified palygorskites decreased with increasing the dosages. A Lagergren pseudo-second order model best described the kinetics of adsorption of Mn2+ onto the modified palygorskites.

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47

Gueneau, Basile, Nathalie Marlin, Alain Deronzier, and Dominique Lachenal. "Pulp delignification with oxygen and copper(II)-polyimine complexes." Holzforschung 68, no. 4 (May 1, 2014): 377–84. http://dx.doi.org/10.1515/hf-2013-0134.

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Abstract Ten Cu(II)-polyimine complexes were tested as potential catalysts in oxygen delignification of softwood kraft pulps. The ligands were chosen from the terpyridine and the phenanthroline families, including several neocuproines. One diamine-phenanthrene (daphen) was also investigated. The main purpose was to examine whether the presence of methyl or phenyl substituents would direct the oxidation toward lignin. As a catalyst for comparison, unsubstituted 1,10-phenanthroline was selected, which is known to activate both delignification and carbohydrate degradation during oxygen bleaching of kraft pulp. The variation of ligands was aiming at the complex solubility and redox potential of the parameters. The experiments were performed on a mixture of mechanical pulp and fully bleached kraft pulps, a fully bleached pulp alone, and an industrial unbleached pulp. Concerning the oxygen activation in delignification of kraft pulp, 4,7-diphenyl-1,10-phenanthroline was as good as 1,10-phenanthroline, but appeared to be more selective, which resulted in a higher DPv of cellulose after treatment. This was interpreted by the structural similarities between the ligand and the kraft lignin and by a better stability of the intermediate complex with lignin. Two Cu(II)-phenanthroline derivatives complexes (4,7- and 5,6-dimethyl-1,10-phenanthroline) were also identified as effective oxygen activators for the removal of native lignin.

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Fagnani, Francesco, Alessia Colombo, Graziella Malandrino, Claudia Dragonetti, and Anna Lucia Pellegrino. "Luminescent 1,10-Phenanthroline β-Diketonate Europium Complexes with Large Second-Order Nonlinear Optical Properties." Molecules 27, no. 20 (October 18, 2022): 6990. http://dx.doi.org/10.3390/molecules27206990.

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Substitution of the diglyme ligand of [Eu(hfa)3(diglyme)] (where hfa is hexafluoroacetylacetonate) with a simple 1,10-phenanthroline leads to a six-fold increase of the product μβEFISH, as measured by the Electric-Field-Induced Second Harmonic generation (EFISH) technique. Similarly, [Eu(tta)3(1,10-phenanthroline)] (where Htta is 2-thenoyltrifluoroacetone) is characterized by a large second-order NLO response. Both 1,10-phenanthroline europium complexes have great potential as multifunctional materials for photonics.

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49

Dehghani, Ali, Mostafa M. Amini, Ezzatollah Najafi, Azadeh Tadjarodi, and Behrouz Notash. "Dibromido(2,9-dimethyl-1,10-phenanthroline-κ2 N,N′)zinc." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (May 26, 2012): m811. http://dx.doi.org/10.1107/s1600536812022738.

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The reaction of equimolar amounts of zinc bromide and 2,9-dimethyl-1,10-phenanthroline in dry methanol provided the title compound, [ZnBr2(C14H12N2)], in good yield. The ZnII ion is coordinated in a distorted tetrahedral environment by two N atoms from the chelating 2,9-dimethyl-1,10-phenanthroline ligand and two bromide ions. There is intermolecular π–π stacking between adjacent phenanthroline units, with centroid–centroid distances of 3.594 (3) and 3.652 (3) Å.

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50

Tsubomura, Taro, Kaoru Kimura, Michihiro Nishikawa, and Toshiaki Tsukuda. "Structures and photophysical properties of copper(i) complexes bearing diphenylphenanthroline and bis(diphenylphosphino)alkane: the effect of phenyl groups on the phenanthroline ligand." Dalton Transactions 44, no. 16 (2015): 7554–62. http://dx.doi.org/10.1039/c5dt00835b.

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Emissive copper(i) complexes bearing a phenanthroline ligand having diphenyl groups and diphosphines were synthesized. The quantum yields are enhanced by the diphenyl groups on the phenanthroline ligand.

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Journal articles on the topic 'Phenanthroline'

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