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Abstract
A series of acetoxybenzoylthioureas derivatives with aryl and amino acid ester side chains were prepared by reaction of acetoxybenzoyl isothiocyanate, an acyloxy benzyl ester-based derivative of aspirin, with aryl amines or amino-functionalized amino acids with overall yields of 46–73%. The products that display a thiourea segment as a linker showed improved antibacterial properties in comparison with aspirin. The structures of the synthesized compounds were characterized by infra red spectroscopy, 13C nuclear magnetic resonance (NMR), and 1H NMR spectroscopy. The compounds were screened for their antibacterial activity by using gram-negative bacteria (E. coli ATCC 8739). [2-(phenylcarbamothioylcarbamoyl)phenyl] acetate showed the highest antibacterial activity against E. coli compared with other synthesized compounds.
Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
GRAPHICAL ABSTRACT
Acknowledgments
The authors wish to thank the University Malaysia Sarawak and the Ministry of Science, Technology, and Innovation (MOSTI) for the financial support through research grants 01(S27)684/2008(19) and FRGS/01(14)/743/2010(29), respectively. The authors would also like to thank Associate Professor Dr. Ling Teck Yee for providing technical help for this manuscript.