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Design, Synthesis and <i>in Vitro</i>Antibacterial Activity of 2-thiomethyl-benzimidazole Derivatives

Advances in Biological Chemistry 2021年第4期11卷 165-177页

作者： Ablo Evrard coulibali siomenan Camara Tchambaga Etienne Toure Daouda Coulibaly Souleymane Sissouma Drissa Adjou Ané Laboratoire de Constitution et Réaction de la Matière UFR Sciences des Structures de la Matière et Technologie Université Félix Houphou&euml t Boigny de Cocody Abidjan C&ocirc te d’Ivoire Département de Biologie UFR des Sciences Biologiques Université Peleforo Gon Coulibaly Korhogo C&ocirc te d’Ivoire

A series of novel substituted benzimidazole (7a - n) derivatives were synthesized and characterized by 1H, 13C Nuclear Magnetic Resonance (NMR) spectra and High Resolution Mass Spectrometry (HRMS). The substitution was done in position -1 and -2 by appropriate groups. These compounds are obtained by N-alkylation reaction with thiomethyl-1H-benzimidazole intermediates (5a - g). Design of intermediates (5a - g) was made by condensation reaction between 2-methylbenzimidazole thiourunium salt

关键词： Antibacterial Activity Benzimidazole 2-Methylbenzimidazole Thiouronium Halide

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Theoretical Investigation on the Stability and Reactivity of Imidazo [1,2-a] Pyridine N-Acylhydrazone Derivatives Using Density Functional Theory

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Computational Chemistry 2024年第1期12卷 1-23页

作者： Camara Tchambaga Etienne Sangare Kassoum Dosso Ouehi Ablo Evrard Sekou Diomande Souleymane Coulibaly siomenan coulibali Laboratoire de Constitution et de Raction de la Matire (LCRM) de lUFR SSMT Universit Flix Houphout-Boigny Abidjan Cte dIvoire Dpartement des Sciences et Technologies Agro-industrielles (STAgI) UFR Agriculture ressources halieutiques et agro-industrie (ARHAI) Universit de San Pedro San Pedro Cte dIvoire Laboratoire des Procds Industriels de Synthse de lEnvironnement et des nergies Nouvelles (LAPISEN) Institut National Polytechnique FlixHouphout-Boigny Yamoussoukro Cte dIvoire

The reactivity and stability of seventeen (17) imidazo [1,2-a]pyridine N-acylhydrazone derivatives were investigated using density functional theory at the B3LYP/6-31+ G (d, p) level. Analysis of the molecular electrostatic potential (MEP) and determination of the dual descriptor revealed that in most cases, the nitrogen atoms of the 6-πelectron conjugation, the oxygen, and the sulfur atom are nucleophilic site. Chemical reactivity of the compounds was assessed through analysis of frontier molecular orbitals (HOMO and LUMO), energy gap (Δℰ), chemical hardness (η), and the softness (S). Consequently, the compound 9e exhibited the lowest reactivity, least electron donating, and the highest stability. This comprehensive study offers valuable insights into the chemical behavior of these derivatives, crucial for further exploration and potential applications.

关键词： N-Acylhydrazones Imidazo [1 2-a] Pyridine DFT Molecular Electrostatic Potential Reactivity Stability

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Synthesis and Antibacterial Activities of New 2-(Benzylthio)pyrimidines and 2-(Benzimidazolylmethylthio)pyrimidines Derivatives

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Open Journal of Medicinal Chemistry 2021年第3期11卷 27-39页

作者： Achi Patrick-Armand coulibali siomenan Zon Doumade Timotou Adéyolé Bolou Eric Touré Daouda Sissouma Drissa Adjou Ané Laboratoire de Constitution et Réaction de la Matière UFR Sciences des Structures de la Matière et Technologie Université Félix Houphou&#235t Boigny de Cocody Abidjan C&#244te d’Ivoire Département de Mathématiques-Physique-Chimie UFR des Sciences Biologiques Université Peleforo Gon Coulibaly Korhogo C&#244te d’Ivoire Centre National de Floristique Université Félix Houphou&#235t-Boigny de Cocody Abidjan C&#244te d’Ivoire Département de Biochimie-Génétique UFR des Sciences Biologiques Université Peleforo Gon Coulibaly Korhogo C&#244te d’Ivoire

A series of 2-(benzylthio)pyrimidines (6a-l) and 2-(benzimidazolylmethylthio)-pyrimidines derivatives (6m and 6n) analogues of ethyl 2-(benzylthio)-6-methyl-4-phenyl-1,4-dihydropyrimidine-5-carboxylates and ethyl 2-(((1H-benzimidazol-2-yl)methyl)thio)-6-methyl-4-phenyl-1,4-dihydropyri-midine-5-carboxylates were prepared and evaluated for antibacterial activity. These compounds were obtained by condensation of 2-thiopyrimidines (4) with benzyl halides or 2-(chloromethyl)-1H

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Novel Mannich Bases of Benzimidazole Derivatives: An Antibacterial Study of Environmental Bacterial Strains

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Advances in Biological Chemistry 2023年第5期13卷 182-191页

作者： Evrard Ablo Ouehi Dosso Bakary Coulibaly Kouassi Franscesco Adingra Penayori Marie-Aimée Coulibaly Armand Patrick Achi Tchambaga Etienne Camara Souleymane Coulibaly siomenan coulibali Laboratoire de Constitution et Réaction de la Matière UFR Sciences des Structures de la Matière et Technologie Université Félix Houphou&#235t-Boigny de Cocody Abidjan C&#244te d’Ivoire Laboratoire des Procédés Industriels de Synthèse de l’Environnement et des énergies Nouvelles (LAPISEN) Institut National Polytechnique Félix Houphou&#235t-Boigny Yamoussoukro C&#244te d’Ivoire Laboratoire d’Agrovalorisation Département de Biochimie-Microbiologie UFR Agroforesterie Université Jean Lorougnon Guédé Daloa C&#244te d’Ivoire

A previous study was conducted on the synthesis and antibacterial evaluation of Mannich bases of 2-(thioalkyl)-1H-methylbenzimidazole derivatives. The results of this study showed that certain 2-(thioalkyl)-1H-methylbenzimidazole and 2-(thioalkyl)-methyl-1-(piperidin-1-ylmethyl)benzimidazole derivatives possess antibacterial activities against clinical strains, such as Escherichia coli, Klebsiella pneumonia (Gram-negative bacteria), Staphylococcus aureus and Pseudomonas aeruginosa (Gram-positive bacteria). Following these favorable results, we extended the antibacterial evaluation of this series of molecules to environmental strains. The aim of this study was to assess the impact of the methyl-piperidine group fixed at position-1 of this new series of benzimidazoles on the antibacterial activity of environmental strains. In addition, we first evaluated the antibacterial activity of four 2-(thioalkyl)methylbenzimidazole derivatives and then that of five 2-(thioalkyl)-methyl-1-(piperidin-1-ylmethyl) benzimidazole derivatives. This study allowed us to show that compounds 1d and 1e could inhibit bacterial growth in vitro of the Enterobacteria P1 strain with inhibition diameters of 17.3 ± 0.6 mm and 10 ± 0.0 mm, respectively. However, addition of methyl-piperidinyl in this series showed that five (5) of 2-(thioalkyl)-methyl-1-(piperidin-1-ylmethyl) benzimidazole derivatives had an inhibitory effect on the in vitro growth of bacterial strains used except on Enterobacteria P2 with inhibition diameters between 10.0 ± 0.8 mm and 27.9 ± 1.4 mm. The introduction of the methyl-piperidinyl group at the 1-position of 2-(thioalkyl)-1H-methylbenzimidazole derivatives greatly improved the antibacterial activity against environmental bacteria such as Escherichia coli A1, A2, A3, and A4 and two Enterobacteria P1.

关键词： Methylbenzimidazole Derivatives Inhibit Bacterial Growth Mannich Base Enterobacteria Escherichia coli

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