Synthesis, characterisation and evaluation of N-mannich bases of 2-substituted Benzimidazole derivatives

Abstract

a b s t r a c tRationale: Benzimidazoles and its derivatives represent one of the mainly biological active classes of literature. Aim: In this present study aimed to synthesize N-mannich bases derivatives compounds bearing of 2-substituted benzimidazole moiety, in order to investigate their possible biological activity. Method: Benzimidazole compounds were prepared from the condensation reaction between ortho phenylene diamine and various acids. Mannich base of newly synthesized Benzimidazole derivatives were synthesized from 2-substituted Benzimidazoles by reacting with secondary amines. The purity of the compounds was ascertained by melting point (m.p) and thin layer chromatography (TLC). Structures of the synthesized compounds were elucidated by spectral data. Antimicrobial assay was performed by microbroth dilution method. Bacterial genomic DNA cleavage was assessed by Agarose gel electrophoresis. Toxicity of the most effective compounds was studied by Brine-shrimp lethality assay. Result: Among the synthesized compounds, compound 5E (a) and (b) was establish to be the most potent against all tested microorganisms. This two compounds exhibited complete bacterial DNA cleavage and non-toxic. Conclusion: These results suggest that it an interesting compound compared to the current therapeutic agents and are considered to investigate further for the same.

Pharmacological and Toxicological Screening of Novel Benzimidazole-Morpholine Derivatives as Dual-Acting Inhibitors

“…The origin of the special interest towards benzimidazole derivatives has been the 5,6-dimethyl-1-(α- d -ribofuranosyl)-benzimidazole structure, which is a basic part of vitamin B12 [ 8 ]. Furthermore, the benzimidazole ring is a structural bioisostere of some of the nucleobases existing in natural nucleotides, which can interact easily with the biopolymers in living systems [ 9 ]; this feature is often accepted as the responsible for its biological importance, either alone or as incorporated into different templates. It has been reported to show many pharmacological activities including antimicrobial, MAO or cyclooxygenase (COX) inhibitory, or anticholinesterase [ 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 ].…”

General Aspects, Applications, and Recent Advancements of 1, 2-Disubstituted Benzimidazole Mannich Bases: A Privileged Scaffold

“…Fluconazole and ampicillin were utilized as reference drugs for antifungal and antibacterial study respectively. The analogues 4(a) and 4(b) were found to be more efficient and potent among other derivatives (12).…”

“…Another series of mannich base of N-(benzimidazol-1-yl methyl)-4-chlorobenzamide analogues (2) were prepared and characterized for antimicrobial action against various bacterial strains like S. aureus, B. subtilis, E. coli and P. aeruginosa along with fungal strains, C. albicans and A. niger. Amongst various synthesized derivatives some compounds showed effective antimicrobial activity (12).…”

Mannich Bases of 2-Substituted Benzimidazoles – A Review

“…17) A series of mannich bases of benzimidazole derivatives were synthesized from o-phenylenediaamine in two steps via benzimidazole intermediates. The anti fungal and anti bacterial activities of synthesized compounds 3a-c (18,19,20) were also checked andit was found that compounds 3a, 3b and 3c showed excellent antibacterial activity and compound 3a showed good antifungal activity than others (Aanadhi et al, 2013). …”