Synthesis and antiproliferative activity of 2-(([1,2,4]triazolo[4,3-b]- pyridazin-6-yloxy)methyl)-2,4-dimethyl-3,4-dihydro-2Hbenzo[b][1,4]oxazine derivatives

Miloš Ilić, Janez Ilaš, Sandra Liekens, Péter Mátyus, Danijel Kikelj

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A small library of [1,2,4]triazolo[4,3-b]pyridazin-6-yloxy derivatives 14-17 of N-benzyl-N-(2-((4-amidinophenoxy)methyl)-2,4-dimethyl-3,4-dihydro-2H- benzo[b][1,4]oxazin-7-yl)-oxalic acid monoamides 1 was prepared by replacement of benzamidine with a [1,2,4]triazolo[4,3-b]pyridazine-6-yl moiety. Thrombin inhibitory and fibrinogen receptor antagonistic activities inherent to benzamidine compounds 1 were lost in the [1,2,4]triazolo[4,3-b]pyridazine derivatives 14-17 which, on the other side, in their ester form (R2 = Et) inhibited the proliferation of endothelial and tumor cells.

Original languageEnglish
Pages (from-to)298-311
Number of pages14
JournalArkivoc
Volume2011
Issue number10
Publication statusPublished - Oct 23 2011

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Keywords

  • 2,4-dimethyl-3,4-dihydro-2H-benzo[b][1,4]- oxazine
  • Benzamidine
  • Cell proliferation
  • Mitsunobu reaction
  • Thrombin inhibitor
  • [1,2,4]Triazolo[4,3-b]pyridazine

ASJC Scopus subject areas

  • Organic Chemistry

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