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

Deme R.;Schlich M.;Mucsi Z.;Karvaly G.;Toth G.;Matyus P.

2016-01-01

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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.