Synthesis and antiproliferative evaluation of 3,5-disubstituted 1,2,4-triazoles containing flurophenyl and trifluoromethanephenyl moieties

Li Ya Wang, Wen Che Tseng, Tian Shung Wu, Kimiyoshi Kaneko, Hiroyuki Takayama, Masayuki Kimura, Wen Chin Yang, Jin Bin Wu, Shin Hun Juang, Fung Fuh Wong

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Abstract

An efficient 1,3-dipolar cycloaddition method was performed for the synthesis of a series of monofluoro- and trifluoromethane-3,5-disubstituted 1,2,4-triazoles. This efficient cycloaddition method was to react hydrazonoyl hydrochlorides with a series of aldehydes in the presence of NEt 3 as catalytic basic agent to provide the corresponding product in 28-94%. Their growth inhibitory results against cancer cells indicated that some of the fluorine- and trifluoromethane-containing compounds could effectively inhibit the growth of NCI-H226 and T-cell leukemia (Jurkat) cells. Among the compounds, trifluoromethane-containing 1,2,4-triazoles possessed the five-membered ring groups on the C-5 position of the triazolic ring, including cyclopentyl, 3-furyl, 3-thienyl, and 2-pyrrolyl, possessed the significant inhibitory activity for NCI-H226 cancer cells.

Original languageEnglish
Pages (from-to)5358-5362
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume21
Issue number18
DOIs
Publication statusPublished - 2011 Sep 15

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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    Wang, L. Y., Tseng, W. C., Wu, T. S., Kaneko, K., Takayama, H., Kimura, M., Yang, W. C., Wu, J. B., Juang, S. H., & Wong, F. F. (2011). Synthesis and antiproliferative evaluation of 3,5-disubstituted 1,2,4-triazoles containing flurophenyl and trifluoromethanephenyl moieties. Bioorganic and Medicinal Chemistry Letters, 21(18), 5358-5362. https://doi.org/10.1016/j.bmcl.2011.07.009