Synthesis of Some Oxadiazole Derivatives as New Anticandidal Agents

Creative Commons License

KAPLANCIKLI Z. A.

MOLECULES, cilt.16, sa.9, ss.7662-7671, 2011 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 16 Sayı: 9
  • Basım Tarihi: 2011
  • Doi Numarası: 10.3390/molecules16097662
  • Dergi Adı: MOLECULES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.7662-7671
  • Anahtar Kelimeler: oxadiazole, pyrimidine, anticandidal activity, ANTIFUNGAL AGENTS, ANTIMICROBIAL ACTIVITIES, INVASIVE CANDIDIASIS, 1,3,4-OXADIAZOLES, RESISTANCE, ALBICANS, AZOLE
  • Bilecik Şeyh Edebali Üniversitesi Adresli: Hayır

Özet

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, (1)H-NMR, (13)C-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, Eskisehir, Turkey), C. albicans (ATCC 90028), C. glabrata (clinical isolate, Osmangazi University, Faculty of Medicine, Eskisehir, 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, Eskisehir, 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.