Biological importance of imidazole nucleus in the new millennium

New imidazole derived thiosemicarbazones and hydrazones were prepared by condensation of 4(5)-imidazole carboxaldehyde, 4-(1H-imidazole-1-yl)benzaldehyde and 4-(1H-imidazole-1-yl)acetophenone with a thiosemicarbazide or hydrazide. All compounds were characterized by quantitative elemental analysis, IR and NMR techniques. Eight structures were determined by single crystal X-ray diffraction. The antifungal activities of the compounds were evaluated. None of the compounds exhibited significant activity against Aspergillus flavus and Candida albicans, while 4(5)-imidazolecarboxaldehyde thiosemicarbazone (ImT) and 4-(1H-imidazole-1-yl)benzaldehyde thiosemicabazone (4ImBzT) were highly and selectively active against Cladosporium cladosporioides. 4(5)-Imidazolecarboxaldehyde benzoyl hydrazone (4(5)ImPh), 4(5)-imidazolecarboxaldehydepara-chlorobenzoyl hydrazone (4(5)ImpClPh), 4(5)-imidazolecarboxaldehyde-paranitrobenzoyl hydrazone (4(5)ImpNO 2 Ph), 4-(imidazole-1-yl)acetophenone-para-chlorobenzoyl hydrazone (4ImAcpClPh) and 4-(imidazole-1-yl)acetophenone-para-nitrobenzoylhydrazone (4ImAcpNO 2 Ph) were highly active against Candida glabrata. 4(5)ImpClPh and 4(5)ImpNO 2 Ph were very effective against C. cladosporioides. In many cases, activity was superior to that of the reference compound nystatin.

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“…Among them seven compounds (2)(3)(4)(5)(6)(7)(8) were original. Microanalyses were compatible with the proposed formulations.…”

Section: Characterization Of the Thiosemicarbazone Derivativesmentioning

confidence: 99%

“…Imidazole derivatives are the most used class of antifungal drugs [1], being active against pathogenic and nonpathogenic fungi [2]. Due to their antifungal properties imidazole-derived compounds have been used in agriculture as effective ingredients for controlling plants pests.…”

Section: Introductionmentioning

confidence: 99%

Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi

et al. 2013

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“…are heterocyclic compounds possessing a wide spectrum of biological activities, especially benzimidazole. [3][4][5][6][7][8][9][10] The biological relevance of benzimidazole-derived compounds is due to their structural similarity to the naturally occurring nucleotides, which facilitate their interaction with biopolymers of living systems. [11] Benzimidazoles, their derivatives and transition metal complexes have received considerable attention in coordination chemistry due to their well-documented biological activities.…”

Section: Introductionmentioning

confidence: 99%

“…These results show that 6 and 7 (binuclear silver complexes) are the most sensitive against both bacteria. These binuclear Ag(I)-NHC complexes (6 and 7) have relatively better anti-bacterial potential compared with their mononuclear counterparts (8)(9)(10), considering the fact that the number of Ag atoms in complexes 6 and 7 is twice that of complexes 8-10. This further underscores the existing literature that the number of silver centres within a complex molecule determines its biological activities.…”

mentioning

confidence: 98%

Benzimidazole‐based silver(I)–N‐heterocyclic carbene complexes as anti‐bacterials: synthesis, crystal structures and nucleic acids interaction studies

Asekunowo

Haque

Razali

et al. 2014

Applied Organom Chemis

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A series of new benzimidazolium salts as N-heterocyclic carbene (NHC) precursors has been synthesized. Reactions of these salts with Ag 2 O with varying metal-to-salt ratio facilitate the formation of a series of new binuclear and mononuclear Ag(I)-NHC complexes. All compounds were characterized using physicochemical and spectroscopic techniques. Single-crystal X-ray diffraction study reveals a binuclear structure for one of the complexes and a mononuclear one for two others. These complexes exist as cationic Ag(I)-NHC complexes with the chelation of carbene carbons to the silver centre in an almost linear manner. The compounds were screened for their anti-bacterial activities against Staphylococcus aureus (ATCC 12600) as a Gram-positive bacterium and Escherichia coli (ATCC 25922) as a Gram-negative bacterium. The results show that both bacteria appear markedly inhibited. Furthermore, the results suggest the possibility of steric variation as a modulation of the anti-bacterial activities. The nuclease activities of the compounds were assessed using gel electrophoresis and the results indicate that these complexes can cleave or degrade DNA and RNA via a non-oxidative mechanism.

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“…Incorporation of an imidazole nucleus, a biologically wellestablished pharmacophore [13,14], in 2-(pyridin-3-yl)-1H-benzo[d]imidazoles and 2-(pyridin-3-yl)-3H-imidazo [4,5-b]pyridine derivatives has resulted in versatile heterocyclic systems with a wide range of biological activity [13,[15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of antibacterial 2-(pyridin-3-yl)-1H-benzo[d]imidazoles and 2-(pyridin-3-yl)-3H-imidazo[4,5-b]pyridine derivatives

Mallemula

Sanghai²,

Himabindu

et al. 2013

Res Chem Intermed

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The increasing clinical importance of drug-resistant fungal and bacterial pathogens has stimulated microbiological research into and development of new antimicrobial agents. Hence, in this study, we synthesized novel series of 2-(pyridin-3-yl)-1H-benzo[d]imidazoles and 2-(pyridin-3-yl)-3H-imidazo[4,5-b]pyridine derivatives. The structures of the compounds were confirmed by spectral and CHN analysis. The compounds were examined for in-vitro antimicrobial activity against Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), and the fungus Candida albicans.

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Biological importance of imidazole nucleus in the new millennium

Cited by 173 publications

References 77 publications

Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi

Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi

Benzimidazole‐based silver(I)–N‐heterocyclic carbene complexes as anti‐bacterials: synthesis, crystal structures and nucleic acids interaction studies

Synthesis and characterization of antibacterial 2-(pyridin-3-yl)-1H-benzo[d]imidazoles and 2-(pyridin-3-yl)-3H-imidazo[4,5-b]pyridine derivatives

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