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Abstract

SYNTHESIS AND BIOLOGICAL INVESTIGATION OF NOVEL N-(((2- (DIMETHYLAMINO)ETHYL) DISULFANYL)METHYL) SUBSTITUTED AMIDE DERIVATIVES

Chandrakant D. Pawar, Dattatraya N. Pansare, Rohini N. Shelke,
Devanand B. Shinde*

ABSTRACT

Objectives: A novel method for synthesis of N-(2-(2-(2-(dimethyl amino) ethyl disulfonyl substituted amides is developed by using simple peptide coupling, N-methylation and displacement reaction in good yields. We have synthesized 26 molecules in gram scale. This method is extremely useful for the synthesis of disulfide compounds in excellent yields. All synthesized compounds were evaluated for antimicrobial activity in vitro. Method: Antimicrobial activity against two bacteria; Staphylococcus aureus (NCIM-2901), Escherichia coli (NCIM-2256) and two fungal strains; Candida albicans (NCIM-3471) and Aspergillus Niger (NCIM-1196). Results: We have synthesized 26 different N-(2-(2-(2- (dimethyl amino)ethyl)disulfonyl) substituted amides compounds (Scheme 1). We have synthesized target in simple three step procedure. We have optimized all the steps. There is no need for purification in first two steps and only silica gel column required in final stage. We have optimized condition for amide formations by varying different coupling reagents, varying bases, varying solvents, reaction time, different equivalents of coupling reagents and purifications. Conclusion: Amongst these, the compounds 7a, 7b, 7c, 7d, 7e, 7f, 7m, 7n and 7v-7z showed highest antibacterial and antifungal activity. The compound 7a-7f exhibited significant antimicrobial activity; the in vitro antimicrobial studies revealed that 7f, 7m, 7n, 7x and 7z are the most active compounds against tested strain, which can be regarded as the promising drug candidate for development of antimicrobial drugs.

Keywords: Disulfides; Amide synthesis; 2-Chloro-N,N-dimethylethanamine; antimicrobial activity.


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