Sulfonamide and carbamate derivatives of 6-chloropurine: synthesis, characterization and antimicrobial activity evaluation

K. Venkata Narayana, D. Subba Rao, G. Madhava, N. Venkateswarlu, T. Vijaya, and C. Naga Raju

Department of Chemistry, Sri Venkateswara University, Tirupati-517502, A. P., India

Research and Development Centre, API Division, Micro Labs Ltd, KIADB INDL Area, Bommasandra, Banglore-560100, Karnataka, India

Department of Botany, Sri Venkateswara University, Tirupati-517 502, A. P., India

Abstract: A series of new sulfonamide derivatives, 9-(substitutedbenzenesulfonyl)-6-chloro-9H-purines 7(a-e) and carbamate derivatives, 6-chloro-purine-9-carboxylic acid substituted alkyl/arylester 9(a-d), have been synthesized through an intermediate, sodium salt of 6-chloro-9(H)-purine (6) which was prepared by the treatment of 6-chloro-9(H)-purine (4) with sodium hydride. Structures of the newly synthesized compounds were elucidated by IR, NMR ( 1H and 13C), mass spectra and elemental analysis. Antimicrobial activity against three bacterial strains and three fungal strains at two different concentrations, 100 and 200 µg/mL including MIC values was investigated. Bio-screening data disclosed that most of the sulfonamide derivatives, 7a, 7c and 7d, and one carbamate derivative 9a showed promising antimicrobial activity having MIC values in the range of 18.0-25.0 µg/mL.

Keywords : 6-Chloro-9(H)-purine; sulfonamides; carbamates; antimicrobial activity; minimum inhibitory concentration. © 2014 ACG Publications. All rights reserved.