Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Synthesis and Antimicrobial Activity of 2-Trifluoroacetonylbenzoxazole Ligands and Their Metal Complexes
Genki WatanabeHiroshi SekiyaEiji TamaiRyosuke SaijoHidemitsu UnoShigeki MoriToru TanakaJun MakiMasami Kawase
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2018 Volume 66 Issue 7 Pages 732-740

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Abstract

Three 2-fluoroacetonylbenzoxazole ligands 1ac and their new Zn(II) complexes 2ac have been synthesized. In addition, syntheses of new metal [Mg(II), Ni(II), Cu(II), Pd(II), and Ag(I)] complexes from 1a have been also described. The molecular and crystal structures of six metal complexes 2b and 2dh were determined by single-crystal X-ray diffraction analyses. Their antibacterial activities against six Gram-positive and six Gram-negative bacteria were evaluated by minimum inhibitory concentrations (MIC), which were compared with those of appropriate antibiotics and silver nitrate. The results indicate that some metal compounds have more antibacterial effects in comparison with free ligands and have preferred antibacterial activities that may have potential pharmaceutical applications. Noticeably, the Ag(I) complex 2h exhibited low MIC value of 0.7 µM against Pseudomonas aeruginosa, which was even superior to the reference drug, Norfloxacin with that of 1.5 µM. Against P. aeruginosa, 2h is bacteriostatic, exerts the cell surface damage observed by scanning electron microscopy (SEM) and is less likely to develop resistance. The new 2h has been found to display effective antimicrobial activity against a series of bacteria.

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© 2018 The Pharmaceutical Society of Japan
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