Versatile synthesis of novel tetrahydroquinolines as potentially active semicarbazide-sensitive amine oxidase (SSAO) inhibitors via tert-Amino effect

Ruth Deme, Michele Schlich, Zoltán Mucsi, Gellért Karvaly, Gergo Tóth, P. Mátyus

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3 Citations (Scopus)

Abstract

Several aminomethyl tetrahydroquinoline derivatives were synthesized in a facile three-ste procedure, in order to develop a semicarbazide-sensitive amine oxidase (SSAO) inhibitor library as proved by in vitro test on rat aorta microsomal fraction. The efficient microwave-Assisted cisdiastereoselectiv cyclization of 2-dicyanovinyl-Tert-Anilines is based on tert-Amino effect as thermal isomerization reaction. The cyclized dicarbonitrile intermediates were subjected to decyanation reaction and a subsequent reduction, providing the biologically active aminomethy tetrahydroquinoline derivatives.

Original languageEnglish
Pages (from-to)164-196
Number of pages33
JournalArkivoc
Volume2016
Issue number5
DOIs
Publication statusPublished - Sep 21 2016

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Keywords

  • Diastereoselective cyclization
  • Microwave-Assisted reaction
  • SSAO activity
  • Tert-Amino effect
  • Tetrahydroquinolines

ASJC Scopus subject areas

  • Organic Chemistry

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