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Synthesis of Some Oxadiazole Derivatives as New Anticandidal Agents

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, 26470 Eskişehir, Turkey
Molecules 2011, 16(9), 7662-7671; https://doi.org/10.3390/molecules16097662
Received: 25 July 2011 / Revised: 23 August 2011 / Accepted: 6 September 2011 / Published: 7 September 2011
(This article belongs to the Section Medicinal Chemistry)
In this study, 5-[(pyrimidin-2-ylthio)methyl]-1,3,4-oxadiazole-2(3H)-thione (3) was synthesized via the ring closure reaction of 2-(pyrimidin-2-ylthio)acetohydrazide (2) with carbon disulphide. New oxadiazole derivatives 4a-f were obtained by the nucleophilic substitution reaction of compound 3 with various phenacyl bromides. The chemical structures of the compounds were elucidated by IR, 1H-NMR, 13C-NMR and FAB+-MS spectral data and elemental analyses. The newly synthesized derivatives 4a-f were tested in vitro by using a microbroth dilution method against C. albicans (clinical isolate, Osmangazi University, Faculty of Medicine, Eskişehir, Turkey), C. albicans (ATCC 90028), C. glabrata (clinical isolate, Osmangazi University, Faculty of Medicine, Eskişehir, Turkey), C. tropicalis (NRRL Y-12968), C. krusei (NRRL Y-7179), C. parapsilosis (NRRL Y- 12696), C. albicans (NRRL Y-12983), C. glabrata (clinical isolate, Anadolu University, Faculty of Science, Department of Biology, Eskişehir, Turkey). Among these compounds, compound 4a was found to be the most potent derivative (MIC = 0.007–0.06 versus ketoconazole: 0.001–0.007 mg/mL) against Candida species, except C. tropicalis and C. krusei when compared with the standard antifungal ketoconazole. View Full-Text
Keywords: oxadiazole; pyrimidine; anticandidal activity oxadiazole; pyrimidine; anticandidal activity
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MDPI and ACS Style

Kaplancikli, Z.A. Synthesis of Some Oxadiazole Derivatives as New Anticandidal Agents. Molecules 2011, 16, 7662-7671. https://doi.org/10.3390/molecules16097662

AMA Style

Kaplancikli ZA. Synthesis of Some Oxadiazole Derivatives as New Anticandidal Agents. Molecules. 2011; 16(9):7662-7671. https://doi.org/10.3390/molecules16097662

Chicago/Turabian Style

Kaplancikli, Zafer Asim. 2011. "Synthesis of Some Oxadiazole Derivatives as New Anticandidal Agents" Molecules 16, no. 9: 7662-7671. https://doi.org/10.3390/molecules16097662

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