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Synthesis, Characterization, and Evaluation for Antibacterial and Antifungal Activities of N-Heteroaryl Substituted Benzene Sulphonamides

DOI: 10.1155/2014/419518

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Abstract:

The synthesis and biological activity of N-heteroaryl substituted benzene sulphonamides (3a–h) were successful. Simple condensation reaction of benzene sulphonyl chloride (1) with substituted heteroaromatic compounds (2a–h) under dry pyridine and acetone gave the target molecules (3a–h) in good to excellent yield. The compounds were characterized using FTIR, 1HNMR, and 13CNMR. The compounds were screened for antibacterial activity against E. coli, Salmonella typhi, P. aeruginosa, B. cereus, K. pneumonia, and Sarcina??lutea and antifungal activity against C. albicans and A. niger. The results of the antimicrobial activity showed improved biological activity against some tested organisms. 1. Introduction A large number of sulphonamide derivatives have ultimately been reported to show substantial protease inhibitory properties [1]. Sulphonamides are synthetic antimicrobial agents which act as competitive inhibitors of the enzyme dihydropteroate synthetase (DHPS) [2]. The basic sulphonamide group, SO2NH, occurs in various biological active compounds widely used as antimicrobial drugs, antithyroid agents, antitumor, antibiotics, and carbonic anhydrase inhibitors [3, 4]. Clinically, sulphonamides are used to treat several urinary tract infections and gastrointestinal infections [5]. Aromatic or heteroaromatic sulphonamides that are used as antitumor agent act by inhibiting carbonic anhydrase. Structurally, sulphonamides are similar to p-aminobenzoic acid (PABA) which is a cofactor needed by bacteria for the synthesis of folic acid and therefore could compete for incorporation. Sulphonamide antibiotics are used as veterinary medicines to treat infections in livestock herds [6, 7]. Additionally, sulphonamides are extremely useful pharmaceutical compounds because they exhibit a wide range of biological activities such as anticancer, anti-inflammatory, and antiviral activity [8–12]. The sulphonylation of amines with sulphonyl chlorides in the presence of a base is still being used as the method of choice because of high efficiency and simplicity of the reaction [13]. However, this approach is limited by the formation of undesired disulphonamides with primary amines and by the need of harsh reaction conditions for less nucleophilic amines such as anilines [14]. Additionally, side reactions take place in the presence of a base. Sulphonamides have been used as protecting groups of OH or NH functionalities for easy removal under mild conditions [15, 16]. Resistance to sulphonamides by bacteria is most likely a result of a compensatory increase in the biosynthesis of

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