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Journal of Chemistry
Volume 2016, Article ID 2739832, 7 pages
http://dx.doi.org/10.1155/2016/2739832
Research Article

Synthesis and Bacteriostatic Activities of Bis(thiourea) Derivatives with Variable Chain Length

Department of Chemistry, Faculty of Resources Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia

Received 1 September 2016; Revised 18 November 2016; Accepted 24 November 2016

Academic Editor: Radhey Srivastava

Copyright © 2016 Ainaa Nadiah Abd Halim and Zainab Ngaini. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

A series of 1,4-bis(decoxyphenyl)carbamothioyl-terephthalamide derivatives was successfully synthesised by reaction of benzene-1,4-dicarbonyl isothiocyanate intermediates with long alkyl chain. The alkylation was performed via Williamson etherification of 4-acetamidophenol with bromoalkanes. The synthesised bis(thiourea) derivatives differed in the chain length, CnH2n+1, where , 12, and 14. The structures of all compounds were characterised by elemental CHN analysis, IR, 1H, and 13C NMR spectroscopies. Bacteriostatic activities of bis(thiourea derivatives which consisted of two folds of N-H, C=O, and C=S and long alkyl chain substituents were carried out against Gram-negative bacteria (Escherichia coli, ATCC 25922) via turbidimetric kinetic method. Bis(thiourea) derivatives with and displayed excellent activity against E. coli with MIC of 135 µg/mL and 145 µg/mL, respectively, while bis(thiourea) derivatives with acted as cutoff point with no antibacterial properties. Similar trend was observed in binding affinity to the active site of enoyl ACP reductase (FabI), which demonstrated binding free energy of Kcal/mol and and  Kcal/mol, respectively.