Synthesis and bacteriostatic activities of bis(Thiourea) derivatives with variable Chain Length

Ainaa Nadiah, Abd Halim and Ngaini, Zainab (2016) Synthesis and bacteriostatic activities of bis(Thiourea) derivatives with variable Chain Length. Journal of Chemistry, 2016. ISSN 20909063

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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 n = 10, 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 n = 10 and n = 12 displayed excellent activity against E. coli with MIC of 135 μg/mL and 145 μg/mL, respectively, while bis(thiourea) derivatives with n = 14 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 -5.3 Kcal/mol and -4.9 and -4.8 Kcal/mol, respectively.

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