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

Research output: Contribution to journalArticle

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

Fingerprint

Amine Oxidase (Copper-Containing)
Aniline Compounds
Derivatives
Cyclization
Isomerization
Rats
Microwaves
1,2,3,4-tetrahydroquinoline
Hot Temperature

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Versatile synthesis of novel tetrahydroquinolines as potentially active semicarbazide-sensitive amine oxidase (SSAO) inhibitors via tert-Amino effect. / Deme, Ruth; Schlich, Michele; Mucsi, Zoltán; Karvaly, Gellért; Tóth, Gergo; Mátyus, P.

In: Arkivoc, Vol. 2016, No. 5, 21.09.2016, p. 164-196.

Research output: Contribution to journalArticle

Deme, Ruth ; Schlich, Michele ; Mucsi, Zoltán ; Karvaly, Gellért ; Tóth, Gergo ; Mátyus, P. / Versatile synthesis of novel tetrahydroquinolines as potentially active semicarbazide-sensitive amine oxidase (SSAO) inhibitors via tert-Amino effect. In: Arkivoc. 2016 ; Vol. 2016, No. 5. pp. 164-196.
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