Abstract

SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL STUDY OF SOME NEW BENZIMIDAZOLE-2-THIONE DERIVATIVES

Sanjay K. Patil*, Sudhakar A. Nirmalkar, Hrushikesh P. Deokar and Vaishali S. Nirmalkar

Abstract

A series of Benzimidazole-2-thione derivatives synthesized by reaction of 2-[3/-chloro-1/methylthio-2/-propanol]-1-methyl-1H-benzimidazole 1(a-b) with hydrazine hydrate afford 1/-(1-methyl-1H-benzimidazol-2- yl) sulfanyl-3/-hydrazinylpropan-2/-ol 2(a-b) which on further heating with diethyl carbonate in presence of sodium methoxide gave 2-[3/- amino -5/- sulfanyl methyl -1/, 3/-oxazolidin-2-one]-1-methyl-1Hbenzimidazole 3(a-b) which on further condensation with choloroacetyl chloride gave 2-[3/-(amino-2//- chloro acetamide)-5/- sulfanyl methyl -1/, 3/-oxazolidin-2/-one ]- 1-methyl-1H-benzimidazole 4(a-b) which on further treatment with KSCN gave 2-[3/-(amino-2//- thiocynato acetamide) -5/- sulfanyl methyl -1/, 3/-oxazolidin-2-one ]- 1- methyl-1H-benzimidazole 5(a-b) which when refluxed in presence of solvent DMF formed 2//-imino-[1//-(5/-sulfanylmethyl-1/,3/-oxazolidin-2/-one)-1-methyl-1H-benzimidazole]-1//,3//- thiazolidin-5//-one 6(a-b) which when further refluxed with 2% HCl formed 1//-[ (5/- sulfanyl methyl -1/, 3/-oxazolidin-2/-one)-1-methyl-1H-benzimidazole]-1//,3//-thiazolidin-2//,5//dione 7(a-b). All synthesized novel Benzimidazole-2-thione derivatives were characterized by IR, NMR, Mass Spectroscopy and Elemental analysis. These compounds were screened against a series of Gram positive and Gram negative bacteria and showed significant to moderate activity.

Keywords: Benzimidazole-2-thione, oxazolidine, thiazolidinone, antimicrobial activity.