Synthesis and biological evaluation of 1-(6-methylpyridin-2-yl)-5- (quinoxalin-6-yl)-1,2,3-triazoles as transforming growth factor-β type 1 receptor kinase inhibitors

Fei Li, Yunjeong Park, Jung Mi Hah, Jae Sang Ryu

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17 Scopus citations

Abstract

A series of 1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1,2,3-triazoles has been synthesized and evaluated for their ALK5 inhibitory activity. The 1-(6-methylpyridin-2-yl)-1,2,3-triazoles were assembled by Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition. Following this, quinoxaline was introduced through Pd-catalyzed direct arylation. The synthesized 1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1,2,3-triazoles revealed significant selectivity differences with respect to p38α MAP kinase. In particular, 12k showed 80.8% ALK5 inhibitory activity at a concentration of 10 μM and IC50 value of 4.69 μM, but did not show p38α MAP kinase inhibitory activity (-1.94% inhibition at a concentration of 10 μM).

Original languageEnglish
Pages (from-to)1083-1086
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume23
Issue number4
DOIs
StatePublished - 15 Feb 2013

Keywords

  • 1,2,3-Triazole
  • ALK5
  • Anticancer
  • Click chemistry
  • TGF-β type 1 receptor kinase

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