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Journal articles on the topic 'Hydroxypyridine ligands'

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Published: 4 June 2021

Last updated: 1 February 2022

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1

Breit, Bernhard, and Wolfgang Seiche. "Self-assembly of bidentate ligands for combinatorial homogeneous catalysis based on an A-T base pair model." Pure and Applied Chemistry 78, no. 2 (January 1, 2006): 249–56. http://dx.doi.org/10.1351/pac200678020249.

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A new concept for generation of chelating ligand libraries for homogeneous metal complex catalysis based on self-assembly is presented. Thus, self-assembly of structurally simple monodentate ligands in order to give structurally more complex bidentate ligands is achieved employing hydrogen bonding. Based on this concept and on the 2-pyridone/hydroxypyridine tautomeric system, a new rhodium catalyst was identified which operated with excellent activity and regioselectivity upon hydroformylation of terminal alkenes. In order to generate defined unsymmetrical heterodimeric ligands, an A-T base pair analog-the aminopyridine/isoquinolone system-was developed which allows for complementary hydrogen bonding. Based on this platform, a 4 x 4 phosphine ligand library was screened in the course of the rhodium-catalyzed hydroformylation of 1-octene. A catalyst operating with outstanding activity and regioselectivity in favor of the linear aldehyde was discovered.

2

Kremer, Marius, and Ulli Englert. "Zn and Ni complexes of pyridine-2,6-dicarboxylates: crystal field stabilization matters!" Acta Crystallographica Section E Crystallographic Communications 75, no. 6 (May 31, 2019): 903–11. http://dx.doi.org/10.1107/s2056989019007461.

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Six reaction products of ZnII and NiII with pyridine-2,6-dicarboxylic acid (H2Lig1), 4-chloropyridine-2,6-dicarboxylic acid (H2Lig2) and 4-hydroxypyridine-2,6-dicarboxylic acid (H2Lig3) are used to pinpoint the structural consequences of crystal field stabilization by an incomplete d shell. The pseudo-octahedral ZnII coordination sphere in bis(6-carboxypicolinato)zinc(II) trihydrate, [Zn(C7H4NO4)2]·3H2O or [Zn(HLig1)2]·3H2O, (1), is significantly less regular than that about NiII in the isostructural compound bis(6-carboxypicolinato)nickel(II) trihydrate, [Ni(C7H4NO4)2]·3H2O or [Ni(HLig1)2]·3H2O, (2). The ZnII complexes poly[(4-chloropyridine-2,6-dicarboxylato)zinc(II)], [Zn(C7H2ClNO4)] n or [Zn(Lig2)] n , (3), and poly[[(4-hydroxypyridine-2,6-dicarboxylato)zinc(II)] monohydrate], {[Zn(C7H3NO5)]·H2O} n or {[Zn(Lig3)]·H2O} n , (4), represent two-dimensional coordination polymers with chelating and bridging pyridine-2,6-dicarboxylate ligands in which the coordination polyhedra about the central cations cannot be associated with any regular shape; their coordination environments range between trigonal–bipyramidal and square-pyramidal geometries. In contrast, the corresponding adducts of the diprotonated ligands to NiII, namely triaqua(4-chloropyridine-2,6-dicarboxylato)nickel(II), [Ni(C7H2ClNO4)(H2O)3] or [NiLig2(OH2)3)], (5), and triaqua(4-hydroxypyridine-2,6-dicarboxylato)nickel(II) 1.7-hydrate, [Ni(C7H3NO5)(H2O)3]·1.7H2O or [NiLig3(OH2)3)]·1.7H2O, (6), feature rather regular octahedral coordination spheres about the transition-metal cations, thus precluding the formation of analogous extended structures.

3

Bare, William D., Nathan H. Mack, J. N. Demas, and B. A. DeGraff. "pH-Dependent Photophysical Behavior of Rhenium Complexes Containing Hydroxypyridine Ligands." Applied Spectroscopy 58, no. 9 (September 2004): 1093–100. http://dx.doi.org/10.1366/0003702041959316.

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4

Oh, Yunghee, Chul Ho Lee, Burm Jong Lee, and Byoung Chul Shin. "Photoluminescent Europium Complexes with Oxygen and/or Nitrogen Donating Ligands." Key Engineering Materials 277-279 (January 2005): 966–71. http://dx.doi.org/10.4028/www.scientific.net/kem.277-279.966.

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The reaction of EuX3 ·nH2O (X=Cl¯ , NO3¯ ), a- pyridoin anion (P) and 2,2¢-dipyridylamine in ethanol solution yields a hydroxo complex, EuP2(OH) 2(H2O) 2, which is characterized by NMR, IR, and elemental analyses. Europium complexes coordinated by nitrogen donating ligands such as 2,2¢-dipyridylamine or 2¢-hydroxypyridine are unstable in solution and are prone to decompose to europium hydroxo complex and pyridinium amine salt. The UV and PL spectra of europium complexes are reported and a decomposition mechanism is proposed.

5

Perdih, Franc. "Copper(II) bis(4,4,4-trifluoro-1-phenylbutane-1,3-dionate) complexes with pyridin-2-one, 3-hydroxypyridine and 3-hydroxypyridin-2-one ligands: molecular structures and hydrogen-bonded networks." Acta Crystallographica Section C Structural Chemistry 73, no. 11 (October 19, 2017): 960–67. http://dx.doi.org/10.1107/s2053229617014875.

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Copper(II) bis(4,4,4-trifluoro-1-phenylbutane-1,3-dionate) complexes with pyridin-2-one (pyon), 3-hydroxypyridine (hpy) and 3-hydroxypyridin-2-one (hpyon) were prepared and the solid-state structures of (pyridin-2-one-κO)bis(4,4,4-trifluoro-3-oxo-1-phenylbutan-1-olato-κ2 O,O′)copper(II), [Cu(C10H6F3O2)2(C5H5NO)] or [Cu(tfpb-κ2 O,O′)2(pyon-κO)], (I), bis(pyridin-3-ol-κO)bis(4,4,4-trifluoro-3-oxo-1-phenylbutan-1-olato-κ2 O,O′)copper(II), [Cu(C10H6F3O2)2(C5H5NO)2] or [Cu(tfpb-κ2 O,O′)2(hpy-κO)2], (II), and bis(3-hydroxypyridin-2-one-κO)bis(4,4,4-trifluoro-3-oxo-1-phenylbutan-1-olato-κ2 O,O′)copper(II), [Cu(C10H6F3O2)2(C5H5NO2)2] or [Cu(tfpb-κ2 O,O′)2(hpyon-κO)2], (III), were determined by single-crystal X-ray analysis. The coordination of the metal centre is square pyramidal and displays a rare example of a mutual cis arrangement of the β-diketonate ligands in (I) and a trans-octahedral arrangement in (II) and (III). Complex (II) presents the first crystallographic evidence of κO-monodentate hpy ligation to the transition metal enabling the pyridine N atom to participate in a two-dimensional hydrogen-bonded network through O—H...N interactions, forming a graph-set motif R 2 2(7) through a C—H...O interaction. Complex (III) presents the first crystallographic evidence of monodentate coordination of the neutral hpyon ligand to a metal centre and a two-dimensional hydrogen-bonded network is formed through N—H...O interactions facilitated by C—H...O interactions, forming the graph-set motifs R 2 2(8) and R 2 2(7).

6

Pivarcsik, Tamás, Gábor Tóth, Nikoletta Szemerédi, Anita Bogdanov, Gabriella Spengler, Jakob Kljun, Jerneja Kladnik, Iztok Turel, and Éva A. Enyedy. "Comparison of Solution Chemical Properties and Biological Activity of Ruthenium Complexes of Selected β-Diketone, 8-Hydroxyquinoline and Pyrithione Ligands." Pharmaceuticals 14, no. 6 (May 27, 2021): 518. http://dx.doi.org/10.3390/ph14060518.

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In this work, the various biological activities of eight organoruthenium(II) complexes were evaluated to reveal correlations with their stability and reactivity in aqueous media. Complexes with general formula [Ru(η6-p-cymene)(X,Y)(Z)] were prepared, where (X,Y) represents either an O,O-ligand (β-diketone), N,O-ligand (8-hydroxyquinoline) or O,S-pyrithione-type ligands (pyrithione = 1-hydroxypyridine-2(1H)-thione) with Cl− or 1,3,5-triaza-7-phosphaadamantane (PTA) as a co-ligand (Z). The tested complexes inhibit the chlamydial growth on HeLa cells, and one of the complexes inhibits the growth of the human herpes simplex virus-2. The chlorido complexes with N,O- and O,S-ligands displayed strong antibacterial activity on Gram-positive strains including the resistant S. aureus (MRSA) and were cytotoxic in adenocarcinoma cell lines. Effect of the structural variation on the biological properties and solution stability was clearly revealed. The decreased bioactivity of the β-diketone complexes can be related to their lower stability in solution. In contrast, the O,S-pyrithione-type complexes are highly stable in solution and the complexation prevents the oxidation of the O,S-ligands. Comparing the binding of PTA and the chlorido co-ligands, it can be concluded that PTA is generally more strongly coordinated to ruthenium, which at the same time decreased the reactivity of complexes with human serum albumin or 1-methylimidazole as well as diminished their bioactivity.

7

Hejrani-Dalir, Ali, Masumeh Tabatabaee, and Ali Sheibani. "Synthesis and crystal structure of 2-amino-3-hydroxypyridinium dioxido(pyridine-2,6-dicarboxylato-κ3O2,N,O6)vanadate(V) and its conversion to nanostructured V2O5." Acta Crystallographica Section C Structural Chemistry 71, no. 2 (January 12, 2015): 89–92. http://dx.doi.org/10.1107/s2053229614027983.

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2-Amino-3-hydroxypyridinium dioxido(pyridine-2,6-dicarboxylato-κ3O2,N,O6)vanadate(V), (C5H7N2O)[V(C7H3NO4)O2] or [H(amino-3-OH-py)][VO2(dipic)], (I), was prepared by the reaction of VCl3with dipicolinic acid (dipicH2) and 2-amino-3-hydroxypyridine (amino-3-OH-py) in water. The compound was characterized by elemental analysis, IR spectroscopy and X-ray structure analysis, and consists of an anionic [VO2(dipic)]−complex and an H(amino-3-OH-py)+counter-cation. The VVion is five-coordinated by oneO,N,O′-tridentate dipic dianionic ligand and by two oxide ligands. Thermal decomposition of (I) in the presence of polyethylene glycol led to the formation of nanoparticles of V2O5. Powder X-ray diffraction (PXRD) and scanning electron microscopy (SEM) were used to characterize the structure and morphology of the synthesized powder.

8

Argibay-Otero, Saray, Rosa Carballo, and Ezequiel M. Vázquez-López. "Crystal structure offac-tricarbonylchloridobis(4-hydroxypyridine)rhenium(I)–pyridin-4(1H)-one (1/1)." Acta Crystallographica Section E Crystallographic Communications 73, no. 10 (September 29, 2017): 1551–54. http://dx.doi.org/10.1107/s2056989017013512.

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The asymmetric unit of the title compound, [ReCl(C5H5NO)2(CO)3]·C5H5NO, contains one molecule of the complexfac-[ReCl(4-pyOH)2(CO)3] (where 4-pyOH represents 4-hydroxypyridine) and one molecule of pyridin-4(1H)-one (4-HpyO). In the molecule of the complex, the Re atom is coordinated to two N atoms of the two 4-pyOH ligands, three carbonyl C atoms, in a facial configuration, and the Cl atom. The resulting geometry is slightly distorted octahedral. In the crystal structure, both fragments are associated by hydrogen bonds; two 4-HpyO molecules bridge between two molecules of the complex using the O=C group as acceptor for two different HO– groups of coordinated 4-pyOH from two neighbouring metal complexes. The resulting square arrangements are extented into infinite chains by hydrogen bonds involving the N—H groups of the 4-HpyO molecule and the chloride ligands. The chains are further stabilized by π-stacking interactions.

9

Jotani, Mukesh M., Hadi D. Arman, Pavel Poplaukhin, and Edward R. T. Tiekink. "Bis(N,N-diethyldithiocarbamato-κ2S,S′)(3-hydroxypyridine-κN)zinc and bis[N-(2-hydroxyethyl)-N-methyldithiocarbamato-κ2S,S′](3-hydroxypyridine-κN)zinc: crystal structures and Hirshfeld surface analysis." Acta Crystallographica Section E Crystallographic Communications 72, no. 12 (November 1, 2016): 1700–1709. http://dx.doi.org/10.1107/s205698901601728x.

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The common feature of the molecular structures of the title compounds, [Zn(C5H10NS2)2(C5H5NO)], (I), and [Zn(C4H8NOS2)2(C5H5NO)], (II), are NS4donor sets derived fromN-bound hydroxypyridyl ligands and asymmetrically chelating dithiocarbamate ligands. The resulting coordination geometries are highly distorted, being intermediate between square pyramidal and trigonal bipyramidal for both independent molecules comprising the asymmetric unit of (I), and significantly closer towards square pyramidal in (II). The key feature of the molecular packing in (I) is the formation of centrosymmetric, dimeric aggregates sustained by pairs of hydroxy-O—H...S(dithiocarbamate) hydrogen bonds. The aggregates are connected into a three-dimensional architecture by methylene-C—H...O(hydroxy) and methyl-C—H...π(chelate) interactions. With greater hydrogen-bonding potential, supramolecular chains along thecaxis are formed in the crystal of (II), sustained by hydroxy-O—H...O(hydroxy) hydrogen bonds, with ethylhydroxy and pyridylhydroxy groups as the donors, along with ethylhydroxy-O—H...S(dithiocarbamate) hydrogen bonds. Chains are connected into layers in theacplane by methylene-C—H...π(chelate) interactions and these stack along thebaxis, with no directional interactions between them. An analysis of the Hirshfeld surfaces clearly distinguished the independent molecules of (I) and reveals the importance of the C—H...π(chelate) interactions in the packing of both (I) and (II).

10

Al-Saeedi, Sameerah, Laila Abdel-Rahman, Ahmed Abu-Dief, Shimaa Abdel-Fatah, Tawfiq Alotaibi, Ali Alsalme, and Ayman Nafady. "Catalytic Oxidation of Benzyl Alcohol Using Nanosized Cu/Ni Schiff-Base Complexes and Their Metal Oxide Nanoparticles." Catalysts 8, no. 10 (October 13, 2018): 452. http://dx.doi.org/10.3390/catal8100452.

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In this work, nanosized Cu and Ni Schiff-base complexes, namely ahpvCu, ahpnbCu, and ahpvNi, incorporating imine ligands derived from the condensation of 2-amino-3-hydroxypyridine, with either 3-methoxysalicylaldehyde (ahpv) or 4-nitrobenzaldehyde (ahpnb), were synthesized using sonochemical approach. The structure and properties of the new ligands and their complexes with Ni(II) and Cu(II) were determined via infrared (IR), nuclear magnetic resonance (NMR), electronic spectra (UV-Vis), elemental analysis (CHN), thermal gravimetric analysis (TGA), molar conductivity (Λm), and magnetic moment (μeff). The combined results revealed the formation of 1:1 (metal: ligand) complexes for ahpvCu and ahpvNi and 1:2 for ahpnbCu. Additionally, CuO and NiO nanoparticles were prepared by calcination of the respective nanosized Cu/Ni complexes at 500 °C, and characterized by powder X-ray diffraction (XRD) and transmission electron microscopy (TEM). Significantly, the as-prepared nanosized Schiff-base Cu/Ni complexes and their oxides showed remarkable catalytic activity towards the selective oxidation of benzyl alcohol (BzOH) in aqueous H2O2/ dimethylsulfoxide (DMSO) solution. Thus, catalytic oxidation of BzOH to benzaldehyde (BzH) using both ahpvCu complex and CuO nanoparticles in H2O2/DMSO media at 70 °C for 2 h yielded 94% and 98% BzH, respectively, with 100% selectivity.

11

Kladnik, Jerneja, Samuel Ristovski, Jakob Kljun, Andrea Defant, Ines Mancini, Kristina Sepčić, and Iztok Turel. "Structural Isomerism and Enhanced Lipophilicity of Pyrithione Ligands of Organoruthenium(II) Complexes Increase Inhibition on AChE and BuChE." International Journal of Molecular Sciences 21, no. 16 (August 6, 2020): 5628. http://dx.doi.org/10.3390/ijms21165628.

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The increasing number of Alzheimer’s disease (AD) cases requires the development of new improved drug candidates, possessing the ability of more efficient treatment as well as less unwanted side effects. Cholinesterase enzymes are highly associated with the development of AD and thus represent important druggable targets. Therefore, we have synthesized eight organoruthenium(II) chlorido complexes 1a–h with pyrithione-type ligands (pyrithione = 1-hydroxypyridine-2(1H)-thione, a), bearing either pyrithione a, its methyl (b-e) or bicyclic aromatic analogues (f–h) and tested them for their inhibition towards electric eel acetylcholinesterase (eeAChE) and horse serum butyrylcholinesterase (hsBuChE). The experimental results have shown that the novel complex 1g with the ligand 1-hydroxyquinoline-2-(1H)-thione (g) improves the inhibition towards eeAChE (IC50 = 4.9 μM) and even more potently towards hsBuChE (IC50 = 0.2 μM) in comparison with the referenced 1a. Moreover, computational studies on Torpedo californica AChE have supported the experimental outcomes for 1g, possessing the lowest energy value among all tested complexes and have also predicted several interactions of 1g with the target protein. Consequently, we have shown that the aromatic ring extension of the ligand a, though only at the appropriate position, is a viable strategy to enhance the activity against cholinesterases.

12

Kosone, Takashi, Yusuke Suzuki, and Takafumi Kitazawa. "A Novel Bi-Metal NiIICdIISupramolecular Structure with 4-Hydroxypyridine Ligands, [{CdII(4-OHpy)2}{NiII(CN)4}], and Deprotonated 3-Hydroxypyridine Ligands, [{CdII3(3-O−py)2(mea)2}{NiII(CN)4}2]." Bulletin of the Chemical Society of Japan 82, no. 8 (August 15, 2009): 984–86. http://dx.doi.org/10.1246/bcsj.82.984.

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13

Badr, Ahmed M. A., Assem Barakat, Jörg H. Albering, Mona M. Sharaf, Zaheer Ul-Haq, and Saied M. Soliman. "Structure, Antimicrobial Activity, Hirshfeld Analysis, and Docking Studies of Three Silver(I) Complexes-Based Pyridine Ligands." Applied Sciences 10, no. 14 (July 15, 2020): 4853. http://dx.doi.org/10.3390/app10144853.

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Three broad spectrum Ag(I) complexes against MDR (multi drug resistance) and ATCC standard bacteria as well as the fungus C. albicans were presented. The three well-known structurally-related Ag(I) complexes, [Ag(pyridine-3-carboxaldhyde)2NO3], 1, [Ag3(2-pyridone)3(NO3)3]n, 2, and [Ag(3-hydroxypyridine)2]NO3, 3, were prepared by the direct combination of AgNO3 with the corresponding pyridine ligands in a water-ethanol mixture. 1 and 3 are molecular compounds while, 2 is a 2D coordination polymer with sheets bridged by strong homoleptic R2,2(8) hydrogen bonds between ligands giving the ins topology. Different contacts affecting the molecular packing in their crystal structures were computed by employing Hirshfeld analysis. Charge transferences from the ligand groups to Ag(I) were analyzed using natural population analysis. The effect of protonation and metal coordination on the tautomerism of 2-pyridone was analyzed using data from the Cambridge Structure Database (CSD). It was found that Lewis acid attachment to both N and O sites favor a state in between the two formal tautomers. All compounds were significantly more active than 17 tested commercial antibiotics against three clinically isolated strains of Ps. Aeruginosa, with 2 and 3 performing best on average against all ten tested bacterial strains but with 3 containing less Ag per weight. Finally, docking studies were carried out to unravel the inhibition mechanism of the synthesized silver(I) complexes.

14

Mirzaei, Masoud, Hossein Eshtiagh-Hosseini, Zahra Karrabi, and Behrouz Notash. "catena-Poly[[di-μ2-aqua-hexaaquabis(μ3-4-oxidopyridine-2,6-dicarboxylato)trimanganese(II)] trihydrate]: a new one-dimensional coordination polymer based on a trinuclear MnIIcomplex of chelidamic acid." Acta Crystallographica Section C Crystal Structure Communications 69, no. 10 (September 28, 2013): 1140–43. http://dx.doi.org/10.1107/s0108270113025006.

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4-Hydroxypyridine-2,6-dicarboxylic acid (chelidamic acid, hypydc[H]H2) reacts with MnCl2·2H2O in the presence of piperazine in water to afford the title complex, {[Mn3(C7H2NO5)2(H2O)8]·3H2O}nor {[Mn3(hypydc)2(H2O)8]·3H2O}n. This compound is a one-dimensional coordination polymer, with the twofold symmetric repeat unit containing three metal centres. Two different coordination geometries are observed for the two independent MnIImetal centres,viz.a distorted pentagonal bipyramid and a distorted octahedron. The 4-oxidopyridine-2,6-dicarboxylate anions and two of the water molecules act as bridging ligands. The zigzag-like geometry of the coordination polymer is stabilized by hydrogen bonds. O—H...O and C—H...O hydrogen bonds and water clusters consolidate the three-dimensional network structure.

15

Gao, Shan, Zhen-Zhong Lu, Li-Hua Huo, Hui Zhao, and Jing-Gui Zhao. "Unprecedented strong blue fluorescent cadmium(II) coordination polymer based on neutral and deprotonated 3-hydroxypyridine ligands." Inorganic Chemistry Communications 8, no. 1 (January 2005): 96–98. http://dx.doi.org/10.1016/j.inoche.2004.11.008.

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16

Hommes, Paul, and Hans-Ulrich Reissig. "Synthesis of highly functionalized 2,2'-bipyridines by cyclocondensation of β-ketoenamides – scope and limitations." Beilstein Journal of Organic Chemistry 12 (June 9, 2016): 1170–77. http://dx.doi.org/10.3762/bjoc.12.112.

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The scope of a flexible route to unsymmetrically functionalized bipyridines is described. Starting from 1,3-diketones 1a–e, the corresponding β-ketoenamines 2a–e were converted into different β-ketoenamides 3a–g by N-acylation with 2-pyridinecarboxylic acid derivatives. These β-ketoenamides were treated with a mixture of TMSOTf and Hünig’s base to promote the cyclocondensation to 4-hydroxypyridine derivatives. Their immediate O-nonaflation employing nonafluorobutanesulfonyl fluoride provided the expected 4-nonafloxy-substituted bipyridine derivatives 5a–g in moderate to good overall yields. The bipyridyl nonaflates are excellent precursors for palladium-catalyzed reactions as demonstrated by representative Suzuki and Sonogashira couplings. Thus, a library of specifically substituted bipyridine derivatives was generated, showing the versatility of the simple 1,3-diketone-based approach to this important class of ligands.

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Galván-Hidalgo, José M., Diana M. Roldán-Marchán, Arturo González-Hernández, Teresa Ramírez-Apan, Antonio Nieto-Camacho, Simón Hernández-Ortega, and Elizabeth Gómez. "Organotin (IV) complexes from Schiff bases ligands based on 2-amino-3-hydroxypyridine: synthesis, characterization, and cytotoxicity." Medicinal Chemistry Research 29, no. 12 (September 22, 2020): 2146–56. http://dx.doi.org/10.1007/s00044-020-02630-4.

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18

Rodriguez, Christina, Rachel Kiriakopoulos, Lana K. Hiscock, Zachary Schroeder, and Louise N. Dawe. "Pyridazinones from maleic hydrazide: a new substrate for the Mitsunobu reaction." Canadian Journal of Chemistry 98, no. 6 (June 2020): 273–77. http://dx.doi.org/10.1139/cjc-2019-0474.

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Crystal engineered organic frameworks assembled using hydrogen bonding are known, and examples constructed from hydroxypyridine/pyridone as the dominant source of hydrogen bonding have been reported. Less explored are analogous systems based on maleic hydrazide. Herein, a two-step route (Mitsunobu followed by Schiff base reactions) to asymmetrically substituted pyridazinones from maleic hydrazide (step 1) is reported with 2-, 3-, or 4-pyridinecarboxaldehyde (step 2). Upon reaction with 4-pyridinecarboxaldehyde, single crystals suitable for analysis via X-ray diffraction were obtained. Careful examination of this solid state structure and comparison with a large number of related structures in the Cambridge Structural Database revealed a pyridazinone (vs. pyridazinol) core and persistent [Formula: see text] “head-to-tail” hydrogen bonded dimers. Although these pyridazinones were originally considered suitable for use as ligands for metal cation coordination, challenges in achieving this outcome were encountered.

19

Chiriac, Florentina L., Monica Iliş, Augustin Madalan, Doina Manaila-Maximean, Mihail Secu, and Viorel Cîrcu. "Thermal and Emission Properties of a Series of Lanthanides Complexes with N-Biphenyl-Alkylated-4-Pyridone Ligands: Crystal Structure of a Terbium Complex with N-Benzyl-4-Pyridone." Molecules 26, no. 7 (April 1, 2021): 2017. http://dx.doi.org/10.3390/molecules26072017.

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This work focuses on the investigation of the liquid crystalline behavior and luminescence properties of the lanthanide complexes of Eu(III), Sm(III) and Tb(III) with N-biphenyl-alkylated-4-pyridone ligands. The organic ligands having a biphenyl group attached via a long flexible spacer with either 9 or 10 carbon atoms were synthesized by the reaction between 4-hydroxypyridine and the corresponding bromide compounds. The chemical structures of the organic and lanthanide complexes were assigned based on elemental analysis, single-crystal X-ray diffraction, 1H, 13C NMR and IR spectroscopies, and thermogravimetric analysis (TGA). The X-ray diffraction analysis of a parent compound shows that the lanthanide ions are surrounded by three monodentate pyridone ligands and three bidentate nitrate ions, giving a 9-coordinate environment. The mesogenic behavior and the type of liquid crystalline phases exhibited by the new complexes were analyzed by differential scanning calorimetry (DSC) and polarizing optical microscopy (POM), and powder X-ray diffraction (XRD) studies. Only the lanthanide complexes with longer spacer (10) display a monotropic SmA phase, typically on a short thermal range (less than 10 °C). The complexes with shorter flexible chains (9) show no liquid crystalline properties with melting temperatures lower than their analogs with longer spacers. The emission spectra recorded in solid state at room temperatures show typical emission bands for each lanthanide ion employed (Eu(III), Tb(III) and Sm(III)).

20

Liu, Cai-Ming, De-Qing Zhang, Xiang Hao, and Dao-Ben Zhu. "Trinuclear [CoIII2-LnIII] (Ln=Tb, Dy) Single-Ion Magnets with Mixed 6-Chloro-2-Hydroxypyridine and Schiff Base Ligands." Chemistry - An Asian Journal 9, no. 7 (May 7, 2014): 1847–53. http://dx.doi.org/10.1002/asia.201402001.

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21

Chattopadhyay, Swarup, Phillip E. Fanwick, and Richard A. Walton. "The reactions of 2-hydroxypyridine ligands with Re2Cl4(μ-dppm)2 (dppm=Ph2PCH2PPh2) that lead to 2-pyridonate complexes." Inorganica Chimica Acta 357, no. 3 (February 2004): 764–68. http://dx.doi.org/10.1016/j.ica.2003.06.018.

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22

Feng, X., Q. Q. Sun, X. G. Shi, L. Y. Wang, and J. S. Zhao. "Hydrothermal synthesis and properties of a new 3D lanthanum supramolecule based on the 4-hydroxypyridine 2,6-dicarboxylate and water ligands." Russian Journal of Coordination Chemistry 37, no. 1 (January 2011): 57–63. http://dx.doi.org/10.1134/s1070328410121012.

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Gao, Hong-Ling, Long Yi, Bin Zhao, Xiao-Qing Zhao, Peng Cheng, Dai-Zheng Liao, and Shi-Ping Yan. "Synthesis and Characterization of Metal−Organic Frameworks Based on 4-Hydroxypyridine-2,6-dicarboxylic Acid and Pyridine-2,6-dicarboxylic Acid Ligands." Inorganic Chemistry 45, no. 15 (July 2006): 5980–88. http://dx.doi.org/10.1021/ic060550j.

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24

Nakatsuji, Yohji, Jerald S. Bradshaw, Pui-Kwan Tse, Giuseppi Arena, Bruce E. Wilson, N. Kent Dalley, and Reed M. Izatt. "New proton-ionizable macrocyclic ligands. Synthesis, basicity, reactions, and structures of two aza crown ethers containing the 4-hydroxypyridine unit." Journal of the Chemical Society, Chemical Communications, no. 12 (1985): 749. http://dx.doi.org/10.1039/c39850000749.

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25

Izatt, Reed M., Jerald S. Bradshaw, Mary Lee Colter, Yohji Nakatsuji, Neil O. Spencer, Michael F. Brown, Giuseppi Arena, Pui Kwan Tse, and Bruce E. Wilson. "Proton-ionizable crown compounds. 2. Synthesis, complexation properties, and structural studies of macrocyclic polyether-diester ligands containing a 4-hydroxypyridine subcyclic unit." Journal of Organic Chemistry 50, no. 24 (November 1985): 4865–72. http://dx.doi.org/10.1021/jo00224a043.

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26

Lobana, Tarlok S., and Paramjit K. Bhatia. "Chemistry of mercaptopyridines and related ligands. Part 3. Novel examples of copper(II)–tertiary phosphine complexes stabilized by 1-hydroxypyridine-2-thione." J. Chem. Soc., Dalton Trans., no. 8 (1992): 1407–10. http://dx.doi.org/10.1039/dt9920001407.

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27

Sharma, Garima, and Anudeep Kumar Narula. "Synthesis and optoelectronic properties of three Eu(III)-dipicolinate complexes based on α-picolinic acid, 2-aminopyridine and 2-hydroxypyridine as secondary ligands." Journal of Materials Science: Materials in Electronics 26, no. 2 (November 16, 2014): 1009–17. http://dx.doi.org/10.1007/s10854-014-2497-7.

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28

Castillo, Oscar, Antonio Luque, Sonia Iglesias, Pablo Vitoria, and Pascual Román. "Synthesis, crystal structure, thermal behaviour and magnetic properties of a novel one-dimensional copper(II) complex containing neutral and deprotonated 3-hydroxypyridine ligands." New Journal of Chemistry 24, no. 10 (2000): 771–75. http://dx.doi.org/10.1039/b004072j.

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29

Mirzaei, Masoud, Vito Lippolis, M. Carla Aragoni, Manoochehr Ghanbari, Mojtaba Shamsipur, Franc Meyer, Serhiy Demeshko, and Seied Mahdi Pourmortazavi. "Extended structures in copper(II) complexes with 4-hydroxypyridine-2,6-dicarboxylate and pyrimidine derivative ligands: X-ray crystal structure, solution and magnetic studies." Inorganica Chimica Acta 418 (July 2014): 126–35. http://dx.doi.org/10.1016/j.ica.2014.04.027.

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30

Breeze, Steven R., and Suning Wang. "Hydrogen-bond-directed assembly of one-dimensional and two-dimensional polymeric copper(II) complexes with trifluoroacetate and hydroxypyridine as ligands: syntheses and structural investigations." Inorganic Chemistry 32, no. 26 (December 1993): 5981–89. http://dx.doi.org/10.1021/ic00078a014.

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31

Zhou, Tao, Robert C. Hider, and Xiaole Kong. "Mode of iron(iii) chelation by hexadentate hydroxypyridinones." Chemical Communications 51, no. 26 (2015): 5614–17. http://dx.doi.org/10.1039/c4cc10339d.

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Abstract:

Tripodal hexadentate hydroxypyridin-4-ones are increasingly utilised as iron(iii) and gallium(iii) ligands, their attachment to proteins being particularly useful for positron emission tomography (PET). A tripodal ligand NTA(BuHP)₃, which is reported to form 1 : 1 iron(iii) and gallium(iii) complexes in aqueous, media forms 2 : 2 complexes under physiological conditions.

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Bhat, Irshad Ahmad, Iruthayaraj Avinash, and Ganapathi Anantharaman. "Nickel(II)- and Palladium(II)-NHC Complexes from Hydroxypyridine Functionalized C,O Chelate Type Ligands: Synthesis, Structure, and Catalytic Activity toward Kumada–Tamao–Corriu Reaction." Organometallics 38, no. 8 (February 19, 2019): 1699–708. http://dx.doi.org/10.1021/acs.organomet.8b00878.

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33

Saberi, Sedigheh, Zeynab Zarrabi, Lotfollah Saghaie, Afshin Fassihi, and Nader Pestechian. "Synthesis and comparison of anti-Leishmania major activity of antimony and iron complexes of 3-hydroxypyran-4-one and 3-hydroxypyridine-4-one as bi-dentate ligands." Journal of Reports in Pharmaceutical Sciences 9, no. 2 (2020): 177. http://dx.doi.org/10.4103/jrptps.jrptps_64_18.

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34

Derikvand, Zohreh, Gholam Reza Talei, Hossein Aghabozorg, Marilyn M. Olmstead, Azadeh Azadbakht, Andya Nemati, and Jafar Attar Gharamaleki. "Synthesis, Crystal Structure, Spectroscopic, Electrochemical and Antimicrobial Properties of Cu(II) Complex with the Mixed Ligands of 2,9-Dimethyl-1,10-phenanthroline and 4-Hydroxypyridine-2,6-dicarboxylic Acid." Chinese Journal of Chemistry 28, no. 11 (November 2010): 2167–73. http://dx.doi.org/10.1002/cjoc.201090358.

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35

Zahid, Kanwal, Shazia Nisar, Saima Imad, Shazia Perveen, Shazia Ghaffar, and Nasreen Fatima. "Synthesis and Characterization of Homo and Mixed Ligand Complexes of Fe(III) with Hydroxypyridinone and Hydroxypyranone Type Ligands." Pakistan Journal of Scientific & Industrial Research Series A: Physical Sciences 63, no. 1 (March 18, 2020): 12–17. http://dx.doi.org/10.52763/pjsir.phys.sci.63.1.2020.12.17.

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Abstract:

Hydroxypyridinone and hydroxypyranone are known to be used for the treatment of iron overload by chelation therapy for a long time. Both the ligands have their own side effects when used as medicines. In the present study homo and mixed ligand complexes of both the ligands with iron were prepared and characterized by UV-visible spectrophotometry, Potentiometric study, IR spectroscopy, SEM/EDX and XRD. Overlay spectra obtained from UV-visible spectroscopy of our studied system show the formation of different types of species and confirm that mixed ligand complex is different from the other two systems. Potentiometric titration curves of homo and mixed ligand complexes show the formation of different types of species at different pH and confirm the formation of mixed ligand complex. The comparative results of SEM images of these systems show different surface topologies and hence conform to the formation of mixed ligand complex.

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Ma, Michelle T., Levente K. Meszaros, Brett M. Paterson, David J. Berry, Maggie S. Cooper, Yongmin Ma, Robert C. Hider, and Philip J. Blower. "Tripodal tris(hydroxypyridinone) ligands for immunoconjugate PET imaging with 89Zr4+: comparison with desferrioxamine-B." Dalton Transactions 44, no. 11 (2015): 4884–900. http://dx.doi.org/10.1039/c4dt02978j.

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Abstract:

A tris(hydroxypyridinone) chelator coordinates the PET imaging isotope, ⁸⁹Zr⁴⁺, rapidly and quantitatively under ambient conditions, but a ⁸⁹Zr-labelled tris(hydroxypyridinone)-immunoconjugate is not stable to in vivo demetallation.

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Cheng, Chen, Yulin Chen, Yue Cao, Yongmin Ma, and Robert C. Hider. "Synthesis and characterization of methyl substituted 3-hydroxypyridin-4-ones and their complexes with iron(III)." Canadian Journal of Chemistry 96, no. 3 (March 2018): 293–98. http://dx.doi.org/10.1139/cjc-2017-0545.

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Abstract:

Methyl substituted 3-hydroxypyridin-4(1H)-ones have been synthesized. The pKa values and Fe3+ affinity constants of these ligands were studied. The introduction of an electron-donating methyl group at a different position of pyridinone ring markedly influences the pKa values of 3-hydroxy and 4-oxo groups. The pFe3+ values were also affected and are in the range of 17.6–20.7. The findings can be used to guide a design of 3-hydroxypyridin-4-ones with desirable pKa and pFe3+ values.

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Deblonde, Gauthier J. P., Trevor D. Lohrey, and Rebecca J. Abergel. "Inducing selectivity and chirality in group IV metal coordination with high-denticity hydroxypyridinones." Dalton Transactions 48, no. 23 (2019): 8238–47. http://dx.doi.org/10.1039/c9dt01031a.

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39

Sadhu, Biswajit, and Vijayakriti Mishra. "The coordination chemistry of lanthanide and actinide metal ions with hydroxypyridinone-based decorporation agents: orbital and density based analyses." Dalton Transactions 47, no. 46 (2018): 16603–15. http://dx.doi.org/10.1039/c8dt03262a.

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Abstract:

Ligand-to-metal charge transfer, orbital-mixing, chelatoaromatic effect and topological constraints control the binding of lanthanide and actinide ions to hydroxypyridinone-based decorporation agents.

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Yih, Kuang-Hway, Hsiao-Fen Wang, Keh-Feng Huang, Chang-Chi Kwan, and Gene-Hsiang Lee. "The Nitrogen-Assisted Triphenylphosphine Displacement of 3-Hydroxypyridine and 3-Aminopyridine Ligands in Palladium(II) Complexes: Crystal Structures of [Pd(PPh3)Br]2{μ,η2-C5H3N(OH)}2and [Pd(PPh3)Br]2{μ,η2-C5H3N(NH2)}2." Journal of the Chinese Chemical Society 56, no. 4 (August 2009): 718–24. http://dx.doi.org/10.1002/jccs.200900107.

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41

Szigethy, Géza, and Kenneth N. Raymond. "Hexadentate Terephthalamide(bis-hydroxypyridinone) Ligands for Uranyl Chelation: Structural and Thermodynamic Consequences of Ligand Variation(1)." Journal of the American Chemical Society 133, no. 20 (May 25, 2011): 7942–56. http://dx.doi.org/10.1021/ja201511u.

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42

Piyamongkol, Sirivipa, Yong M Ma, Xiao L Kong, Zu D Liu, Mutlu D Aytemir, Dick van der Helm, and Robert C Hider. "Amido-3-hydroxypyridin-4-ones as Iron(III) Ligands." Chemistry - A European Journal 16, no. 21 (April 15, 2010): 6374–81. http://dx.doi.org/10.1002/chem.200902455.

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43

Zhou, Ying-Jun, Xiao-Le Kong, Jun-Pei Li, Yong-Min Ma, Robert C. Hider, and Tao Zhou. "Novel 3-hydroxypyridin-4-one hexadentate ligand-based polymeric iron chelator: synthesis, characterization and antimicrobial evaluation." MedChemComm 6, no. 9 (2015): 1620–25. http://dx.doi.org/10.1039/c5md00264h.

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Abstract:

A novel 3-hydroxypyridin-4-one hexadentate-based copolymeric iron chelator was prepared. The polymer was found to possess high iron affinity and appreciable inhibitory activity against both Gram-positive and Gram-negative bacteria.

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Leeaphon, Malee, Phillip E. Fanwick, and Richard A. Walton. "Reactions of the polyhydride complex ReH7(PPh3)2 with hydroxypyridine and mercaptopyridine ligands. Formation of hydrido complexes of rhenium(III), rhenium(IV), and rhenium(V) and the characterization of eight-coordinate isomers in the solid state and in solution." Inorganic Chemistry 30, no. 26 (December 1991): 4986–95. http://dx.doi.org/10.1021/ic00026a025.

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45

Gerlach, Deidra L., Ismael Nieto, Corey J. Herbst-Gervasoni, Gregory M. Ferrence, Matthias Zeller, and Elizabeth T. Papish. "Crystal structures of bis- and hexakis[(6,6′-dihydroxybipyridine)copper(II)] nitrate coordination complexes." Acta Crystallographica Section E Crystallographic Communications 71, no. 12 (November 4, 2015): 1447–53. http://dx.doi.org/10.1107/s205698901502037x.

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Abstract:

Two multinuclear complexes synthesized from Cu(NO3)2and 6,6′-dihydroxybipyridine (dhbp) exhibit bridging nitrate and hydroxide ligands. The dinuclear complex (6,6′-dihydroxybipyridine-2κ2N,N′)[μ-6-(6-hydroxypyridin-2-yl)pyridin-2-olato-1:2κ3N,N′:O2](μ-hydroxido-1:2κ2O:O′)(μ-nitrato-1:2κ2O:O′)(nitrato-1κO)dicopper(II), [Cu2(C10H7N2O2)(OH)(NO3)2(C10H8N2O2)] or [Cu(6-OH-6′-O-bpy)(NO3)(μ-OH)(μ-NO3)Cu(6,6′-dhbp)], (I), with a 2:1 ratio of nitrate to hydroxide anions and one partially deprotonated dhbp ligand, forms from a water–ethanol mixture at neutral pH. The hexanuclear complex bis(μ3-bipyridine-2,2′-diolato-κ3O:N,N′:O′)tetrakis(6,6′-dihydroxybipyridine-κ2N,N′)tetrakis(μ-hydroxido-κ2O:O′)bis(methanol-κO)tetrakis(μ-nitrato-κ2O:O′)hexacopper(II), [Cu6(C10H6N2O2)2(CH4O)2(OH)4(NO3)4(C10H8N2O2)4] or [Cu(6,6′-dhbp)(μ-NO3)2(μ-OH)Cu(6,6′-O-bpy)(μ-OH)Cu(6,6′dhbp)(CH3OH)]2, (II), with a 1:1 NO3–OH ratio and two fully protonated and fully deprotonated dhbp ligands, was obtained by methanol recrystallization of material obtained at pH 3. Complex (II) lies across an inversion center. Complexes (I) and (II) both display intramolecular O—H...O hydrogen bonding. Intermolecular O—H...O hydrogen bonding links symmetry-related molecules forming chains along [100] for complex (I) with π-stacking along [010] and [001]. Complex (II) forms intermolecular O—H...O hydrogen-bonded chains along [010] with π-stacking along [100] and [001].

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Yadav, Paras Nath, Laxman Bhattrai, and Pramod K. Mehta. "Palladium(II) Complex of the 5-Hydroxypyridine-2-carbaldehyde N(4)-ethylthiosemicarbazone: Synthesis and Characterization." Journal of Nepal Chemical Society 28 (May 6, 2013): 34–41. http://dx.doi.org/10.3126/jncs.v28i0.8040.

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Abstract:

The novel complex of 5-hydroxypyridine-2-carbaldehyde N(4)-ethylthiosemicarbazone (HPyEt) with plalladium(II) have been prepared and characterized by elemental analysis, IR, 1H-NMR, UV-visible spectroscopy and mass spectrometry (FAB). Coordination of the anionic thiosemicarbazone ligand is via the pyridyl nitrogen, imine nitrogen and thiolato sulfur atoms and the fourth coordination site being occupied by chloride ion in square planar geometry. DOI: http://dx.doi.org/10.3126/jncs.v28i0.8040 Journal of Nepal Chemical Society Vol.28, 2011 Page 34-41 Uploaded date: March 6, 2013

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D’Aléo, Anthony, Jide Xu, Evan G. Moore, Christoph J. Jocher, and Kenneth N. Raymond. "Aryl-Bridged 1-Hydroxypyridin-2-one: Sensitizer Ligands for Eu(III)." Inorganic Chemistry 47, no. 14 (July 2008): 6109–11. http://dx.doi.org/10.1021/ic8003189.

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48

Piyamongkol, Sirivipa, Tao Zhou, Zu D. Liu, Hicham H. Khodr, and Robert C. Hider. "Design and characterisation of novel hexadentate 3-hydroxypyridin-4-one ligands." Tetrahedron Letters 46, no. 8 (February 2005): 1333–36. http://dx.doi.org/10.1016/j.tetlet.2004.12.115.

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49

Lord, Sarah J., Noah A. Epstein, Robert L. Paddock, Christopher M. Vogels, Tracy L. Hennigar, Michael J. Zaworotko, Nicholas J. Taylor, William R. Driedzic, Tom L. Broderick, and Stephen A. Westcott. "Synthesis, characterization, and biological relevance of hydroxypyrone and hydroxypyridinone complexes of molybdenum." Canadian Journal of Chemistry 77, no. 7 (July 1, 1999): 1249–61. http://dx.doi.org/10.1139/v99-111.

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Abstract:

We have prepared a number of complexes of the type cis-MoO2L2 where L represents a hydroxypyronato or hydroxypyridinonato ligand. Both the maltol (3-hydroxy-2-methyl-4-pyrone, Hma) and kojic acid (5-hydroxy-2-hydroxymethyl-4-pyrone, Hka) complexes, cis-MoO2(ma)2 (1) and cis-MoO2(ka)2 (2), have been characterized by X-ray diffraction studies. The pyrone ligands are bound to molybdenum in a cis bidentate fashion via the deprotonated hydroxyl groups and the ketone moieties. Crystals of 1 are orthorhombic, a = 12.107 (1), b = 8.6169 (8), c = 16.472 (1) Å, Z = 4, space group Pca21, and those of 2 are monoclinic, a = 8.4591 (5), b = 16.3453 (10), c = 10.2954 (7) Å, β = 103.0320 (10)°, Z = 4, space group P21/c. Hydroxypyridinone molybdenum complexes have been prepared for both maltol and kojic acid derivatives with the substituents Me, n-Pr, CH2Ph, Ph at the ring nitrogen. Crystals of the 3-hydroxy-2-methyl-1-phenyl-4-pyridinone (Hppp) derivative, MoO2(ppp)2 (9), are monoclinic, a = 10.9476 (6), b = 13.5353 (9), c = 17.4877 (10) Å, β = 93.465 (4)°, Z = 4, space group P21/n. Initial investigations into the effects molybdenum compounds have on diabetic hearts are presented. Both Na2MoO4 (used as a control) and 1 were effective in lowering blood glucose and free fatty acid levels. Diabetic rats treated with molybdate showed significant improvements in postischemic cardiac function.Key words: molybdenum, hydroxypyrones, hydroxypyridinones, heart function.

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Kavitha, Palakuri, and K. Laxma Reddy. "Synthesis, Structural Characterization, and Biological Activity Studies of Ni(II) and Zn(II) Complexes." Bioinorganic Chemistry and Applications 2014 (2014): 1–13. http://dx.doi.org/10.1155/2014/568741.

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Abstract:

Ni(II) and Zn(II) complexes were synthesized from tridentate 3-formyl chromone Schiff bases such as 3-((2-hydroxyphenylimino)methyl)-4H-chromen-4-one (HL1), 2-((4-oxo-4H-chromen-3-yl)methylneamino)benzoic acid (HL2), 3-((3-hydroxypyridin-2-ylimino)methyl)-4H-chromen-4-one (HL3), and 3-((2-mercaptophenylimino)methyl)-4H-chromen-4-one (HL4). All the complexes were characterized in the light of elemental analysis, molar conductance, FTIR, UV-VIS, magnetic, thermal, powder XRD, and SEM studies. The conductance and spectroscopic data suggested that, the ligands act as neutral and monobasic tridentate ligands and form octahedral complexes with general formula [M(L1–4)2]·nH2O (M = Ni(II) and Zn(II)). Metal complexes exhibited pronounced activity against tested bacteria and fungi strains compared to the ligands. In addition metal complexes displayed good antioxidant and moderate nematicidal activities. The cytotoxicity of ligands and their metal complexes have been evaluated by MTT assay. The DNA cleavage activity of the metal complexes was performed using agarose gel electrophoresis in the presence and absence of oxidant H2O2. All metal complexes showed significant nuclease activity in the presence of H2O2.