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SYNTHESIS AND ANTIFUNGAL ACTIVITY OF BENZOXAZOLE DERIVATIVES WITH THEIR SAR ANALYSIS BY SAS-MAP

KAMIAR ZOMORODIAN 1, SOGHRA KHABNADIDEH 2, AMIRHOSSEIN SAKHTEMAN 2, BI BI FATEMEH MIRJALILI 3, MOHSEN RANJBAR 2, LEILA ZAMANI 2*

1.Department of Parasitology & Mycology, School of Medicine, Shiraz University of Medical Sciences, Shiraz, I.R. Iran
2.Faculty of Pharmacy and Pharmaceutical Sciences Research Centre, Shiraz University of Medical Sciences, Shiraz, I.R. Iran
3.Department of Chemistry, College of Science, Yazd University, Yazd, P. O. Box 8915813149, Iran

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A simple and efficient method has been developed for the synthesis of benzoxazole derivatives. In the first step, 2-aminophenols reacted with various aldehydes in the presence of titanium supported nano-silica to produce an imine intermediate. Then the imine was oxidized to get the final azole compounds. Eleven derivatives were synthesized (c)-(m) via this simple and environmentally friendly procedure with high yields. The simple methodology (only 2 steps) with high yields for the reactions and easy procedure are the advantages of the newly developed method. The identification and characterization of all the synthesized compounds were confirmed by melting point, thin layer chromatography, FT-IR, 1H NMR and 13C NMR spectral data. Also elemental analysis was applied for five compounds. All the compounds were screened for antimicrobial activity by broth microdilution methods as recommended by CLSI. Of the tested compounds 2-(2,4-dichlorophenyl)-1,3-benzoxazole (g), and 2-(4-chlorophenyl)-1,3-benzoxazole (f) inhibited the growth of all examined fungi, while 2-(4-nitrophenyl)-1,3-benzoxazole (c) exhibited inhibitory activities only against the tested yeasts.