Derivatives of benzimidazole pharmacophore: Synthesis, anticonvulsant, antidiabetic and DNA cleavage studies

In seeking broad spectrum pharmacological activities of benzimidazole derivatives, a group of 4-thiazolidinones 5(a-j) and 1,3,4-oxadiazoles 6(a-j) containing 2-mercapto benzimidazole moiety were synthesized and screened for in vivo anticonvulsant activity by Maximal Electroshock (MES) model and antidiabetic activity using Oral Glucose Tolerance Test (OGTT). Compounds (5c), (5d), (5g) and (5i) exhibited potent anticonvulsant results and (6c), (6d), (6h) and (6i) showed excellent antidiabetic activities and also pharmacophore derived from active molecules suggested that presence of -OH group was a common feature in all active compounds. In DNA cleavage studies, compound (5d) cleaved DNA completely as no trace of DNA was found. On the other hand, a sharp streak was found for compounds (5c), (6a) and (6d). (C) 2010 Elsevier Masson SAS. All rights reserved.