Synthesis, Investigation of Anticancer and Antioxidant Activity of Certain 2,4-Diaryl Substituted Benzodiazepine and Benzothiazepines Derived From Vanillin

In search of new more effective and selective anticancer agents a series of 2-3-methoxy-4-hydroxy phenyl-4-p-substituted phenyl1-H-15-benzodiazepines 2a-j and 2-3-methoxy-4-hydroxy phenyl-4-P-substituted phenyl 23-dihydro-15-benzothiazepines 3a-j were synthesized from the corresponding chalcone intermediates derived from the reaction between vanillin and substituted acetophenones by condensing with o-phenylenediamine and o-aminothiophenol respectively. Completion of reaction was monitored by TLC compounds were purified by recrystallization and structures were confirmed by UV IR 1HNMR 13CNMR and Mass spectral data. Title compounds were screened for anticancer activity against A549 Lung carcinoma cell line by MTT and antioxidant activity by DPPH radical scavenging assays. 5-Flurouracil and ascorbic acid were used as standard drugs. Among the compounds evaluated in the series compound 3i emerged showing highly active anticancer and antioxidant activity with a IC50 value of 19.20microM and 0.023microM respectively. The compounds that exhibited excellent to good antioxidant activity did not exhibit good anticancer activity. Thus some of the title compounds were found to possess good anticancer and antioxidant activity warranting further research.nbsp