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

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.

• Authors: 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
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 21 Issue 18 Pg. 5358-62 (Sep 15 2011) ISSN: 1464-3405 [Electronic] England
• PMID: 21802949 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Crown Copyright © 2011. Published by Elsevier Ltd. All rights reserved.

Chemical References

• Antineoplastic Agents
• Triazoles
• 1,2,4-triazole

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Cell Proliferation (drug effects)
• Chemistry Techniques, Synthetic
• Cyclization
• Dose-Response Relationship, Drug
• Drug Screening Assays, Antitumor
• Humans
• Molecular Structure
• Stereoisomerism
• Structure-Activity Relationship
• Triazoles (chemical synthesis, chemistry, pharmacology)