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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
Author(s) -
Madácsi Ramóna,
Traj Péter,
Hackler László,
Nagy Lajos I.,
Kari Beáta,
Puskás László G.,
Kanizsai Iván
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3800
Subject(s) - chemistry , thio , pyridine , thiophene , reactivity (psychology) , catalysis , lewis acids and bases , cyanate , organic chemistry , combinatorial chemistry , medicine , alternative medicine , pathology
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 CuOAc 2 (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.