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Synthesis and biological assessment of six novel 2-substituted mercaptobenzimidazole derivatives is performed. The title compounds are characterized by their analytical and spectral data. All the synthesized compounds are screened for their anti-ulcer and anti-microbial activity. 2-(1H-benzimidazole-2-sulfinyl) –N-(4-benzyloxy-phenyl)-acetamide, N-(4-benzyloxy-phenyl)-4-(1H-benzimidazole-2-sulfinyl)-butyramide, N-(4-benzyloxy phenyl)-4-(5-methoxy 1H-benzimidazole-2-sulfinyl)-butyramide showed significant antiulcer activity. All the compounds moderate antibacterial and antifungal activity.