Synthesis and biological evaluation of 4,5,6,7-tetrahydrothieno[2,3-c]pyridine–based β-aminonitriles and their derivatives: β-amino carboxamides, (thio)ureas, and tetracycles

Ramóna Madácsi, Péter Traj, László Hackler, Lajos I. Nagy, Beáta Kari, László G. Puskás, Iván Kanizsai

Research output: Contribution to journalArticle

Abstract

The preparation and cytotoxic characterization of 4,5,6,7-tetrahydrothieno[2,3-c]pyridine–based β-aminonitriles, β-amino carboxamides, and their (thio)urea and annulated derivatives were accomplished. Following a synthetic route involving Gewald three-component reactions (G-3CR) and a Lewis acid–catalyzed iso (thio)cyanate coupling, 30 compounds were prepared for antitumor evaluation. For derivatizations, a catalytic amount of CuOAc2 (20 mol%) was essential for improving the reactivity of either the C-2 amino function of thiophene or isocyanates. The synthesized analogues demonstrated a weak to moderate antitumor activity in a low micromolar range against A549 and K562 cancer cell lines.

Original languageEnglish
JournalJournal of Heterocyclic Chemistry
DOIs
Publication statusAccepted/In press - Jan 1 2019

ASJC Scopus subject areas

  • Organic Chemistry

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