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.

A new series of aspirin bearing alkylated amines moieties 1–12 were synthesised by reacting isothiocyanate with a series of aniline derivatives in overall yield of 16–56%. The proposed structures of all the synthesised compounds were confirmed using elemental analysis, FTIR, and 1H and  13C NMR spectroscopy. All compounds were evaluated for antibacterial activities against E. coli and S. aureus via turbidimetric kinetic and Kirby Bauer disc diffusion method. Compound 5 bearing meta -CH3 substituent showed the highest relative inhibition zone diameter against tested bacteria compared to ortho and para substituent. Furthermore, aspirin derivatives bearing shorter chains exhibited better bacterial inhibition than longer alkyl chains.

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In this study, hexasubstituted thiourea was carried out via reaction of isothiocyanato cyclophosphazene intermediates with a series of aromatics amines and amino acids in a one-pot reaction system. The reaction was not as straightforward as typical thiourea synthesis. Six unexpected thiourea derivatives a-f were formed in the presence of cyclotriphosphazene moieties in good yields (53-82%). The structures of a-f were characterized by elemental analysis and FTIR, 1 H, 13 C, and 31 P NMR spectroscopies. The occurrence of reverse thioureas formation in a one-pot reaction system is discussed. The possible binding interaction of the synthesised thiourea a-b in comparison to the predicted phenyl thiourea a-b and the targeted a with enzyme enoyl ACP reductase (FabI) is also discussed. Molecular docking of the targeted hexasubstituted thiourea a is able to give higher binding affinity of −7.5 kcal/mol compared to a-b (−5.9 kcal/mol and −6.3 kcal/mol) and thiourea a-b (−4.5 kcal/mol and −4.7 Kcal/mol).

In searching for drugs from natural product scaffolds has gained interest among researchers. In this study, a series of twelve halogenated thiourea (ATX 1-12) via chemical modification of aspirin (a natural product derivative) and evaluated for cytotoxic activity against nasopharyngeal carcinoma (NPC) cell lines, HK-1 via MTS-based colorimetric assay. The cytotoxicity studies demonstrated that halogens at meta position of ATX showed promising activity against HK-1 cells (IC 50 value 15 mM) in comparison to cisplatin, a positive cytotoxic drug (IC 50 value ¼8.9 ± 1.9 mM). ATX 11, bearing iodine at meta position, showed robust cytotoxicity against HK-1 cells with an IC 50 value of 4.7 ± 0.7 mM. Molecular docking interactions between ATX 11 and cyclooxygenase-2 demonstrated a robust binding affinity value of À8.1 kcal/mol as compared to aspirin's binding affinity value of À6.4 kcal/mol. The findings represent a promising lead molecule from natural product with excellent cytotoxic activity against NPC cell lines.

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