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Journal articles on the topic 'Bi-heterocycles'

Author: Grafiati

Published: 4 June 2021

Last updated: 11 February 2022

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1

M. Abadleh, Mohammed, Mustafa M. El-Abadelah, Firas F. Awwadi, and Monther S. Zreid. "Bis-Heterocycles. Part II. Tetrahydro-3,3'-bi(1,2,4,5-oxatriazines)." HETEROCYCLES 98, no. 2 (2019): 205. http://dx.doi.org/10.3987/com-18-14015.

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2

Kinjo, Rei, and Bochao Su. "Construction of Boron-Containing Aromatic Heterocycles." Synthesis 49, no. 14 (June 6, 2017): 2985–3034. http://dx.doi.org/10.1055/s-0036-1588832.

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Boron-containing aromatic systems exhibit unique electronic properties and reactivities that have been extensively studied for a long time. This review highlights the recent developments in the synthesis of aromatic boron-containing heterocycles. The organization of the contents is based on the sizes of rings and the heteroatoms other than boron. Early work in the field is briefly introduced, but the main focus is on recent reports published during the period of 2008 through 2016.1 Introduction2 Five-Membered Rings2.1 Borole Derivatives2.2 B,N-Heterocycles2.3 B,O-Heterocycles3 Six-Membered Rings3.1 Borabenzene Derivatives3.2 Boratabenzene Derivatives3.3 1,4-Diborabenzene3.4 B,N-Heterocycles3.5 B,E-Heterocycles (E = O, S, P, Te)4 Three-Membered Rings4.1 Borirenes4.2 Azadiboriridines4.3 Triboracyclopropenyl Dianion5 Four-Membered Rings5.1 bicyclo-Tetraborane(4)5.2 1,3-Diborete5.3 B,E-Heterocycles (E = N, P, As, Sb, Bi, O, S, Se)6 Seven-Membered Rings (Borepines)7 Conclusion and Perspective

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3

Dockendorff, Chris, Patrick W. Faloon, Andrew Germain, Miao Yu, Willmen Youngsaye, Partha P. Nag, Melissa Bennion, et al. "Discovery of bisamide-heterocycles as inhibitors of scavenger receptor BI (SR-BI)-mediated lipid uptake." Bioorganic & Medicinal Chemistry Letters 25, no. 12 (June 2015): 2594–98. http://dx.doi.org/10.1016/j.bmcl.2015.03.074.

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4

Pino-Rios, Ricardo, Alejandro Vásquez-Espinal, Luis Alvarez-Thon, and William Tiznado. "Relativistic effects on the aromaticity of E3M3H3 (E = C–Pb; M = N–Bi) benzene analogues." Physical Chemistry Chemical Physics 22, no. 40 (2020): 22973–78. http://dx.doi.org/10.1039/d0cp04446f.

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The relativistic effects on the aromaticity of a set of benzene analogues, E₃M₃H₃ (E = C–Pb; M = N–Bi) heterocycles, using magnetically induced current density (MICD) and the NICS_zz component of the conventional nucleus independent chemical shift (NICS), is hereby examined.

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5

Mohammad, Hanan H., Mustafa M. El-Abadelah, Salim S. Sabri, Firas F. Awwadi, and Wolfgang Voelter. "Bis-heterocycles. Part I: tetrahydro-5,5′- bi(1,2,4-triazin-6-ones)." Zeitschrift für Naturforschung B 73, no. 12 (December 19, 2018): 965–74. http://dx.doi.org/10.1515/znb-2018-0148.

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AbstractSelected sets of tetrahydro-5,5′-bi(1,2,4-triazines) (1–3) appended with acetyl, benzoyl, and ester moieties at C-3 position and N-1 (p-substituted)phenyl ring have been prepared and characterized by spectral (IR, NMR, MS) data and X-ray diffraction for compound 3a. Their synthesis was achieved in high yield via the reaction of diethyl aminomalonate with various N-(aryl)hydrazonoyl chlorides in the presence of triethylamine.

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6

Yizun, Jin, Gerald E. Adams, John Parrick, and Ian J. Stratford. "Nitro derivatives of bi- and tri-cyclic heterocycles as potential radio-sensitizers." European Journal of Medicinal Chemistry 24, no. 5 (September 1989): 511–16. http://dx.doi.org/10.1016/0223-5234(89)90056-1.

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7

Cruz, Alejandro, Itzia I. Padilla Martínez, and Angel A. Ramos-Organillo. "Methods to Access 2-aminobenzimidazoles of Medicinal Importance." Current Organic Chemistry 23, no. 23 (January 9, 2020): 2573–97. http://dx.doi.org/10.2174/1385272823666191023150201.

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: Benzimidazole (BI) and derivatives are interesting because several of these compounds have been found to have a diversity of biological activities with clinical applications. In view of their importance, the synthesis of BI and its derivatives is still considered as a challenge for synthetic chemists. Examples of compounds used in medicinal chemistry containing BI, as important nucleus, are Astemizole (antihistaminic), Omeprazole (antiulcerative) and Rabendazole (fungicide), some of these compounds have the 2- aminobenzimidazole (2ABI) as base nucleus. The structure of 2ABI derivatives contains a cyclic guanidine moiety, which is interesting because of its free lone pairs, labile hydrogen atoms and planar delocalized structure. The delocalized 10-π electron system and the extension of the electron conjugation with the exocyclic amino group, in 2ABI, making these heterocycles to have amphoteric character. The 2ABI has been used as building blocks for the synthesis of several BI derivatives as medicinally important molecules. On these bases, herein, we present a bibliographic review concerning the recent methodologies used in the synthesis of 2ABIs, including the substituted ones.

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8

Herrera, Lizzi, David E. Stephens, Abigail D'Avila, Kathryn G. George, Hadi Arman, Yu Zhang, George Perry, Ricardo Lleonart, Oleg V. Larionov, and Patricia L. Fernández. "Insights into the structural patterns of the antileishmanial activity of bi- and tricyclic N-heterocycles." Organic & Biomolecular Chemistry 14, no. 29 (2016): 7053–60. http://dx.doi.org/10.1039/c6ob01149g.

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9

Abbasi, Muhammad, Muhammad Ramzan, A. Aziz-Ur-Rehman, Sabahat Siddiqui, Mubashir Hassan, Hussain Raza, Syed Shah, Bushra Mirza, and Sung-Yum Seo. "Structure-activity relationship and in silico study of unique bi-heterocycles: 5-[(2-amino-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazole-2-thiol derivatives." Journal of the Serbian Chemical Society 84, no. 7 (2019): 649–61. http://dx.doi.org/10.2298/jsc180203019a.

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This paper presents the synthesis of some unique bi-heterocyclic hybrid molecules with a thiazole and an oxadiazole ring. The synthesis was initiated by the conversion of ethyl 2-(2-amino-1,3-thiazol-4-yl)acetate (1) to the corresponding 2-(2-amino-1,3-thiazol-4-yl)acetohydrazide (2) by the reaction with hydrazine hydrate in methanol. The treatment of the acid hydrazide, 2, with carbon disulfide gave the bi-heterocyclic nucleophile, 5-[(2-amino-1,3- -thiazol-4-yl)methyl]-1,3,4-oxadiazole-2-thiol (3). Finally, the target compounds, 5a?o, were synthesized by stirring the nucleophile 3 with different electrophiles, 4a?o, in DMF using LiH as a base and an activator. The structures of the newly synthesized molecules were confirmed through spectroscopic techniques, such as IR, EI-MS, 1H-NMR and 13C-NMR. The structure? ?activity relationship of all these bi-heterocycles was established by evaluating them against four enzymes, namely, acetylcholinesterase, butyrylcholinesterase, urease and ?-glucosidase, followed by their in silico study. Moreover, their cytotoxicity was also profiled by killing data of brine shrimps at various concentrations.

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10

Shawali, Ahmad S. "Synthesis and tautomerism of aryl- and hetaryl-azo derivatives of bi- and tri-heterocycles." Journal of Advanced Research 1, no. 4 (October 2010): 255–90. http://dx.doi.org/10.1016/j.jare.2010.07.002.

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11

Periasamy, Mariappan, Boda Venkanna, and Lakavathu Mohan. "Methods for Synthesis of Chiral Alcohols and Their Conversion to Heterocycles Containing Bi‐2‐Naphthyl Moiety." ChemistrySelect 5, no. 3 (January 20, 2020): 1088–91. http://dx.doi.org/10.1002/slct.201903644.

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12

Zaki, Yasser H., and Mahmoud A. Mohamed. "Convenient Synthesis of Some New Bi-heterocycles conataining 3-Aminoquinazolin-4(3H)-one and 1,2,4-Triazole moieties." JOURNAL OF ADVANCES IN CHEMISTRY 10, no. 9 (November 16, 2014): 3108–15. http://dx.doi.org/10.24297/jac.v10i9.876.

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Dicarboxylic acids, thiosemicarbazides and methylanthranilate reacted to give methyl-2-(3-(5-mercapto-4-s-1,2,4-triazol-3-yl)-3-oxoalkylamino)benzoates 4. The laters, cyclized with hydrazine hydrate to give 3-amino-2-((5-mercapto-4 substitued-1,2,4-triazol-3-yl)alkyl)quinazolin-4(3H)-ones 5 which expected to have biological effects.

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13

Chang, Xiaohong, Yu Wang, Yuchun Jiang, Yonglin Guo, Dandan Song, Ximing Song, and Francis Verpoort. "Synthesis, reactivity and characterization of mono-, bi- and tri-nuclear Schiff-base palladacycles with aromatic N-heterocycles." Journal of Organometallic Chemistry 713 (August 2012): 134–42. http://dx.doi.org/10.1016/j.jorganchem.2012.04.026.

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14

Yadav, Jhillu, Basi Subbareddy, Avvaru Krishna, Ailuri Reddy, and Akkirala Narsaiah. "Bi(OTf)3 as Mild, Efficient and Cost-Effective Catalyst for the Alkylation of N-Heterocycles with Epoxides." Letters in Organic Chemistry 5, no. 6 (September 1, 2008): 455–60. http://dx.doi.org/10.2174/157017808785740453.

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15

Bartlett, Stephen, Robert Hodgson, Joanne M. Holland, Matthew Jones, Colin Kilner, Adam Nelson, and Stuart Warriner. "Exploiting predisposition in the stereoselective synthesis of mono-, bi- and tetracyclic oxygen heterocycles: Equilibration between, and trapping of, alternative di- and tetraacetals." Organic & Biomolecular Chemistry 1, no. 13 (2003): 2393. http://dx.doi.org/10.1039/b303089j.

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16

KOEPF, H., and H. BALZ. "ChemInform Abstract: Synthesis of Benzo-Bridged, Five-Membered ES2C2 Heterocycles with ECl Moieties (E: P, As, Sb, Bi) Starting from 1,2,4,5-Tetramercaptobenzene." ChemInform 26, no. 25 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199525184.

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17

Köpf, Hartmut, and Hellfried Balz. "Synthese benzoverbrückter, fünfgliedriger ES2C2-Heterocyclen mit ECl-Baueinheiten (E = P, As, Sb, Bi) ausgehend von 1.2.4.5-Tetramercaptobenzol / Synthesis of Benzo-Bridged, Five-Membered ES2C2 Heterocycles with ECl Moieties (E = P, As, Sb, Bi) Starting from 1,2,4,5-Tetramercaptobenzene." Zeitschrift für Naturforschung B 49, no. 12 (December 1, 1994): 1674–76. http://dx.doi.org/10.1515/znb-1994-1210.

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The benzo-bridged, heterocyclic compounds [E(Cl)S2-1,2]C6H2[4,5-S2E(Cl)] (E = P (1), As (2), Sb (3), Bi (4)) have been obtained as air-stable solids from the reaction of ECl3 with 1.2.4.5-(HS)4C6H2 in diethyl ether. 1-4 are insoluble in common solvents and have been characterized mainly by elemental analyses and their infrared and mass spectra.

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18

Ramzan, Muhammad S., Muhammad A. Abbasi, Aziz Ur-Rehman, Sabahat Z. Siddiqui, Syed A. A. Shah, Muhammad Ashraf, Muhammad A. Lodhi, Farman A. Khan, and Bushra Mirza. "Synthesis of 2-{[5-(aralkyl/aryl)-1,3,4-oxadiazol-2- yl]sulfanyl}-N-(4-methyl-1,3-thiazol-2-yl)acetamides: Novel bi-heterocycles as potential therapeutic agents." Tropical Journal of Pharmaceutical Research 17, no. 5 (June 4, 2018): 913. http://dx.doi.org/10.4314/tjpr.v17i5.23.

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19

Muhammad Athar Abbasi, Muhammad Shahid Ramzan, Aziz-ur-Rehman, Sabahat Zahra Siddiqui, Syed Adnan Ali Shah, Muhammad Arif Lodhi, Farman Ali Khan, and Bushra Mirza. "Synthesis of Novel Bi-Heterocycles as Valuable Anti-Diabetic Agents: 2-({5-((2-Amino-1,3-Thiazol-4-yl)methyl)-1,3,4-Oxadiazol-2-yl}sulfanyl)-N-(Substituted)acetamides." Russian Journal of Bioorganic Chemistry 46, no. 4 (July 2020): 590–98. http://dx.doi.org/10.1134/s1068162020040020.

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20

Olubiyi, Olujide O., Maryam Olagunju, Monika Keutmann, Jennifer Loschwitz, and Birgit Strodel. "High Throughput Virtual Screening to Discover Inhibitors of the Main Protease of the Coronavirus SARS-CoV-2." Molecules 25, no. 14 (July 13, 2020): 3193. http://dx.doi.org/10.3390/molecules25143193.

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We use state-of-the-art computer-aided drug design (CADD) techniques to identify prospective inhibitors of the main protease enzyme, 3CLpro of the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) causing COVID-19. From our screening of over one million compounds including approved drugs, investigational drugs, natural products, and organic compounds, and a rescreening protocol incorporating enzyme dynamics via ensemble docking, we have been able to identify a range of prospective 3CLpro inhibitors. Importantly, some of the identified compounds had previously been reported to exhibit inhibitory activities against the 3CLpro enzyme of the closely related SARS-CoV virus. The top-ranking compounds are characterized by the presence of multiple bi- and monocyclic rings, many of them being heterocycles and aromatic, which are flexibly linked allowing the ligands to adapt to the geometry of the 3CLpro substrate site and involve a high amount of functional groups enabling hydrogen bond formation with surrounding amino acid residues, including the catalytic dyad residues H41 and C145. Among the top binding compounds we identified several tyrosine kinase inhibitors, which include a bioflavonoid, the group of natural products that binds best to 3CLpro. Another class of compounds that decently binds to the SARS-CoV-2 main protease are steroid hormones, which thus may be endogenous inhibitors and might provide an explanation for the age-dependent severity of COVID-19. Many of the compounds identified by our work show a considerably stronger binding than found for reference compounds with in vitro demonstrated 3CLpro inhibition and anticoronavirus activity. The compounds determined in this work thus represent a good starting point for the design of inhibitors of SARS-CoV-2 replication.

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21

FARFAN, N., R. SANTILLAN, B. CASTILLO, P. CARRETERO, M. DE JESUS ROSALES, E. GARCIA-BAEZ, A. FLORES-VELA, J. C. DARAN, and S. HALUT. "ChemInform Abstract: Nuclear Magnetic Resonance and X-Ray Study of a (1,4)Benzothiazino(3,2- b) (1,4)benzothiazine and a Bi(benzothiazolyl), Isomeric N,S- Heterocycles Derived from the Reactions of o-Aminobenzenethiol with Some 1,2-Diones." ChemInform 26, no. 22 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199522024.

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22

Bräu, Elmar, Rüdiger Falke, Andreas Ellner, Mike Beuter, Ute Kolb, and Martin Dräger. "On heterocyclic systems containing bismuth(III) 2. Eight-membered heterocycles Cl/Br/I-M(CH2CH2CH2)2X with lewis acidic group 15 atoms M  As, Sb, Bi and donor atoms X  NR, S: a contribution to the value of the electronegativity of bismuth(III)." Polyhedron 13, no. 3 (January 1994): 365–74. http://dx.doi.org/10.1016/s0277-5387(00)81647-2.

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23

El Ashry, El Sayed H., Laila F. Awad, Mahmoud Nasr, Ahmed A. Kassem, and Mohamed A. Zakaria. "Novel Synthesis of N-(1,3-Dioxoisoindol-2-yl)aminothiocarbohydrazide, and its Arylidenes and Glycosylidines as Precursors for Hybrids with Thiadiazoline Ring. Equilibration of the Glycosylidine Open Chain with the Cyclic Structures and Conformation of the Acyclic Analogues." Current Organic Synthesis 15, no. 7 (October 16, 2018): 1005–13. http://dx.doi.org/10.2174/1570179415666180731123111.

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Aim and Objective: Reaction of phthalic anhydride (1) with thiocarbohydrazide (2) in methanol gave the intermediate (6) whose boiling in water or ethanol gave N-(1,3-dioxoisoindol-2-yl)aminothiocarbohydrazide (5); where its Condensation with aldehydes and aldoses 9a-d afforded the respective thiosemicarbazide derivatives. The manno-derivative 10, the D-galacto derivative 11 and the L-arabino derivative 12 exist in the cyclic pyranosyl structures undergo equilibration, in solution of DMSO, with their acyclic structures. Dehydrative cyclization to the thiadiazoline derivatives and the acyclo C-nucleoside was done by refluxing in acetic anhydride. Materials and Methods: Commercially available solvents and reagents were purified according to the standard procedures. Thin layer chromatography (TLC) was performed on plastic plates Silica Gel 60 F254 (E-Merk, layer thickness 0.2 mm) with detection by UV light absorption. IR spectra were recorded for the compounds in a KBr matrix with a Unicam SP 1025 spectrophotometer. NMR spectra were measured with Jeol spectrometer (500 MHz). Chemical shifts (δ) are given in ppm relative to the signal for TMS as internal standard, and coupling constants in Hz. The 13C NMR spectra were recorded with JEOL spectrometer at 125.7 MHz. The assignments of 1H NMR spectra were based on chemical-shift correlation DQFCOSY spectra, while the assignment of 13C NMR spectra were based on heteronuclear multiple quantum coherence, HMQC experiments. Results: The N-(1,3-dioxoisoindol-2-yl)aminothiocarbohydrazide (5) was prepared, which incorborated the 1,3-dioxoisoindole ring that linked to thiosemicarbazide moiety. Such feature found to be excellent precursor for the synthesis of hybrid of bi-heterocycles, the dioxoisoindolyl and thiadiazoline rings which could of potential biological activity. The reaction of thiocarbohydrazide with phthalic anhydride in a detailed manner and investigate its further reaction with aromatic aldehydes and sugars, then converting them to the target biheterocycles and nucleosides was studied. The conformations of the acyclic alditolyl residues or the acyclic Cnucleosides have been explained. Conclusion: The new functionalized isoindolyl ring with thiosemicarbazide as in N-(1,3-dioxoisoindol-2- yl)aminothiocarbohydrazide (5) resulted from the reaction of phthalic anhydride with thiocarbohydrazide via the intermediate open chain derivative 6. It is a valuable precursor for the synthesis of thiosemicarbazones containing sugar moieties 10-13. Their solutions in DMSO-d6 showed that the products exist in one form after immediate dissolution that equilibrated with time to show a mixture of acyclic and cyclic forms. They have been exploited as scaffolds for generation of potential hybrids of thiadiazoline derivatives containing isoindolyl rings as well as their acyclo C-nucleosides 10a-13a and 14-15. The conformations of the acyclic alditolyl residues or the acyclic C-nucleosides have been deduced from their spectral analysis.

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24

Kurahashi, Takuya, Seijiro Matsubara, Rei Tomifuji, Shunpei Murano, Satoru Teranishi, and Daiki Kuroda. "Multiple Activation Catalyst for Asymmetric [4+2] Cycloaddition of Aldehydes with Dienes." Synlett, September 9, 2021. http://dx.doi.org/10.1055/s-0040-1720885.

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AbstractThe enantioselective oxa-Diels–Alder reaction of nonactivated substrates by utilizing FeCl3 and a 1,1′-bi-2-naphthol (BINOL) derived chiral phosphoric acid as a multiple activation catalyst is reported. Various oxygen-containing six-membered heterocycles were obtained in high yields and in an enantioselective manner. Density functional theory (DFT) calculations elucidate that both Lewis acidic and Brønsted acidic moieties in the catalyst system synergistically activate two lone pairs of an aldehyde to facilitate enantioselective addition reaction of dienes.

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25

Yadav, Jhillu S., Basi V. Subbareddy, Avvaru D. Krishna, Ailuri R. Reddy, and Akkirala V. Narsaiah. "ChemInform Abstract: Bi(OTf)3as Mild, Efficient and Cost-Effective Catalyst for the Alkylation of N-Heterocycles with Epoxides." ChemInform 39, no. 51 (December 16, 2008). http://dx.doi.org/10.1002/chin.200851038.

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