Synthesis of Some Novel 2,4-Disubstituted Thiazoles as Possible Antimicrobial Agents

Authors: Wagle, Shivananda¹; Adhikari, Airody Vasudeva²; Kumari, Nalilu Suchetha³

Source: Phosphorus, Sulfur, and Silicon and the Related Elements, Volume 183, Number 5, May 2008 , pp. 1285-1300(16)

Publisher: Taylor and Francis Ltd

Abstract:

A series of 4-aryl-2-(3-methyl-7-substituted quinoxaline-2-one-1-yl)-1,3-thiazoles (6a-l) and 4-substituted alkyl-2-(3-methyl-7-substituted quinoxaline-2-one-1-yl)-1,3-thiazoles (8a-i) were synthesized in good yield by condensing 2-(3-methyl-7-substituted l,2-oxoquinoxalin-1(2H)-yl)ethanethioamides (5a-c) with substituted phenacyl bromide and dichloroacetone followed by treatment with secondary amines, respectively. The intermediates, 5a-c were conveniently obtained by reacting phosphorus pentasulphide with 2-(3-methyl-7-substituted-2-oxoquinoxalin-1(2H)-yl) acetamides (4a-c) which in turn were synthesized from ethyl (3-methyl-7-substituted-2-oxoquinoxalin-1(2H)-yl) acetates (3a-c) by aqueous ammonia treatment. The newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and Mass spectral and elemental analyses. These compounds were screened for in vitro antibacterial activity against five pathogenic strains and antifungal activity against four fungi. Preliminary results revealed that some of the synthesized compounds showed promising antimicrobial activity.

Keywords: 2,4-Disubstituted thiazoles; 3,7-Dimethyl quinoxalines; antibacterial; antifungal activity; phenacyl bromide

Document Type: Research article

DOI: http://dx.doi.org/10.1080/10426500701641049

Affiliations: 1: Strides Research and Specialty Chemicals Ltd., New Mangalore, India,Department of Chemistry, National Institute of Technology Karnataka, Surathkal, Mangalore, India 2: Department of Chemistry, National Institute of Technology Karnataka, Surathkal, Mangalore, India 3: Department of Biochemistry, Justice K. S. Hegde Medical Academy, Deralakatte, Mangalore, India

Publication date: 2008-05-01

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