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Synthesis and biological properties of 4‐substituted quinolin‐2(1 H )‐one analogues
Author(s) -
Jung JaeChul,
Oh Seikwan,
Kim WonKi,
Park WooKyu,
Kong Jae Yang,
Park OeeSook
Publication year - 2003
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.5570400410
Subject(s) - chemistry , nmda receptor , neurotoxicity , stereochemistry , ring (chemistry) , biological activity , receptor , in vitro , biochemistry , organic chemistry , toxicity
A variety of 4‐substituted quinolin‐2(1 H )‐ones were prepared and evaluated for N ‐methyl‐D‐aspar‐tate (NMDA) receptor binding site activity and their abilities to inhibit neurotoxicity. The 4‐(2‐car‐bethoxyethanamino)‐7‐chloro‐3‐nitroquinolin‐2(1 H )‐one ( 9b ) exhibited favorable NMDA receptor binding site activity and 7‐chloro‐4‐(benzylamino)‐3‐nitroquinolin‐2(1 H )‐one ( 9c ) showed the most potent neurotoxicity among them. The synthetic strategies involve the use of well known keto ester condensation and reductive ring cyclization of intermediates ( 2a‐d ) to afford 4‐substituted quinolin‐2(1 H )‐ones.