Synthesis of 2-[4-(imidazolin-2-ylideneamino)benzyl]-Indan-1-ones as novel potent prostacyclin antagonists

Ching Yuh Chern, Yung Lee Yek, Yu Lin Chen, Wai Ming Kan

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Prostacyclin is involved in many pathological conditions, such as sensitization of inflammation induced pain and isovolumetic distention. Therefore, antagonism of prostacyclin action may be useful in the alleviation of these conditions. In this study, novel potent prostacyclin antagonists, 2-[4-(imidazolin-2-ylideneamino)benzyl]-indan-1 -ones were synthesized from their respective substituted indanones in three steps. The construction of the amino-imidazole moiety of these derivatives is achieved by using in situ generation of chloro-imidazole and reaction with their respective anilines. Thus, these -substituted 2-imidazolines can be prepared safely and efficiently. Moreover, these compounds show potent prostacyclin antagonistic activity by inhibition of prostacyclin agonist induced ERK1/2 phosphorylation in human erythroleukemia cells. Moreover, we observed an increase in activity with the increase in electro-donating property of the substitution on the indanone aromatic ring. Prostacyclin antagonists with increased potency may be designed based on these findings. These compounds may also be invaluable tools for the study of the physiological functions of prostacyclin.

Original languageEnglish
Pages (from-to)846-853
Number of pages8
JournalJournal of the Chinese Chemical Society
Volume55
Issue number4
DOIs
Publication statusPublished - 2008 Jan 1

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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