Synthesis and anticandidal activity of new triazolothiadiazine derivatives

ALTINTOP M. D., KAPLANCIKLI Z. A., Turan-Zitouni G., ÖZDEMİR A., İŞCAN G., AKALIN ÇİFTÇİ G., ...More

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol.46, no.11, pp.5562-5566, 2011 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 46 Issue: 11
  • Publication Date: 2011
  • Doi Number: 10.1016/j.ejmech.2011.09.020
  • Journal Name: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Page Numbers: pp.5562-5566
  • Keywords: Triazole, Triazolothiadiazine, Anticandidal activity, Cytotoxicity, INVASIVE CANDIDIASIS, ANTIFUNGAL, EPIDEMIOLOGY, TRIAZOLE
  • Anadolu University Affiliated: Yes

Abstract

New triazolothiadiazine derivatives were synthesized via the ring closure reaction of 4-amino-5-substituted-2,4-dihydro-3H-1,2,4-triazol-3-thiones with phenacyl bromides. The compounds were tested in vitro against various Candida species and compared with ketoconazole. Among these compounds, the compound bearing cyclohexyl moiety and p-chlorophenyl substituent on triazolothiadiazine ring (21) was found to be the most potent derivative against Candida albicans (ATCC 90028). It is clear that there is a positive correlation between anticandidal activity and two functional moieties, namely cycloaliphatic group and p-chlorophenyl substituent on triazolothiadiazine ring. The compounds were also investigated for their cytotoxic effects using MTT assay. Compound 2a exhibited the highest cytotoxic activity, whereas compound 2f possessed the lowest cytotoxic activity against NIH/3T3 cells. (C) 2011 Elsevier Masson SAS. All rights reserved.