Synthesis and characterization of novel triazol compounds containing a thiophen ring as potential antifungal agents and the structure of 2-(2-hydroxy-2-p-tolyethyl)-5-(thiophen-2-ylmethyl)-4-(4H-1,2,4-triazol-4-yl)-2H-1,2,4-triazol-3(4H)-one


ÜNVER Y. , DUGDU E., SANCAK K. , Er M., Ustabas R.

TURKISH JOURNAL OF CHEMISTRY, vol.34, no.4, pp.551-563, 2010 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 34 Issue: 4
  • Publication Date: 2010
  • Doi Number: 10.3906/kim-0904-11
  • Title of Journal : TURKISH JOURNAL OF CHEMISTRY
  • Page Numbers: pp.551-563

Abstract

A series of new 4-(3,5-disubstitue-4H-1,2,4-triazol-4-yl)-5-(thiophen-2-yl-methyl)-2H-1,2,4-triazol-3(4H)-ones (3a-c) were obtained by reaction N'-1-ethoxy-2-thiophen-2-yl-ethylydene hydrazino carboxylic acid ethyl ester (1) and 4-amino-4H-1,2,4-triazoles (2). 4-(3,5-disubstitue-4H-1,2,4-triazol-4-yl)-2-(2-oxo-2-arylethyl)-5-(thiophen-2-yl-methyl)-2H-1,2,4-triazol-3(4H)-ones (4a-e) and ethyl 2-(4-(3,5-disubstitue-4H-1,2,4-triazol-4-yl)-5-oxo-3-(thiophen-2-ylmethyl)-4,5-dihydro-1,2,4-triazol-1-yl) acetates (6a-c) were obtained by reaction of compounds 3 and bromoacetophenon derivatives and bromo ethylacetate, respectively. Compounds 5a-e were synthesized from the reaction of corresponding compounds 4a-e with NaBH4. Compounds 7a-c were obtained by the reaction compounds 6 and LiAlH4. Seventeen new compounds were synthesized and characterized by elemental analyses, IR, H-1-NMR, and C-13-NMR spectral data. The structure of compound 5d was inferred through IR, H-1-, C-13-NMR, elemental analyses, and X-ray spectral techniques. In addition, the newly synthesized chemicals were screened for their antibacterial and antifungal properties. Among the chemicals tested, 6a and 6b exhibited the highest degree of antifungal activity.