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Synthesis and antimicrobial activity of novel 2-substituted-1Hbenzimidazole derivatives

Khaled R.A.Abdellatif, Heba A.H.Elshemy, Ossama M.El-Badry, Hamdy M.Ragab, Mervat M.El-Enany

The reaction of chloromethyl-1-methyl-1H-benzimidazole (1) with ethyl 4- aminobenzoate yielded the ester 2 which upon hydrazinolysis resulted in [(1-methyl-1H-benzimidazol-2-ylmethyl) amino]benzohydrazide (3).Condensation of 3 with 2-nitrobenzaldhyde afforded the arylidene derivative 4 which was cyclised to thiazolidinone derivative 5. Substituted benzamide 6 and oxadiazole derivative 7 were prepared via reacting 3 with phthalic anhydride and benzoic acid, respectively. Reaction of 3 with 4-chlorophenyl isocyanate and ethyl isothiocyanate gave the corresponding semicarbazide 8 and thiosemicarbazide 9. The thiosemicarbazide 9 was cyclized to triazole and thiadiazole derivatives 10 and 11.Also, reacting 9with both chloroacetic acid and maleic anhydride afforded thiazolidinone derivatives 12 and 13. The prepared compounds were evaluated for in vitro antimicrobial activity using ciprofloxacin and triflucan as standard references.