Synthesis and biological properties of 4-substituted quinolin-2(1H)-one analogues

Jae Chul Jung; Seikwan Oh; Won Ki Kim; Woo Kyu Park; Jae Yang Kong; Oee Sook Park

doi:10.1002/jhet.5570400410

Synthesis and biological properties of 4-substituted quinolin-2(1H)-one analogues

Jae Chul Jung, Seikwan Oh, Won Ki Kim, Woo Kyu Park, Jae Yang Kong, Oee Sook Park

Department of Molecular Medicine

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

A variety of 4-substituted quinolin-2(1H)-ones were prepared and evaluated for N-methyl-D-aspartate (NMDA) receptor binding site activity and their abilities to inhibit neurotoxicity. The 4-(2-carbethoxyethanamino)- 7-chloro-3-nitroquinolin-2(1H)-one (9b) exhibited favorable NMDA receptor binding site activity and 7-chloro-4-(benzylamino)-3- nitroquinolin-2(1H)-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(1H)-ones.

Original language	English
Pages (from-to)	617-623
Number of pages	7
Journal	Journal of Heterocyclic Chemistry
Volume	40
Issue number	4
DOIs	https://doi.org/10.1002/jhet.5570400410
State	Published - 2003

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title = "Synthesis and biological properties of 4-substituted quinolin-2(1H)-one analogues",

abstract = "A variety of 4-substituted quinolin-2(1H)-ones were prepared and evaluated for N-methyl-D-aspartate (NMDA) receptor binding site activity and their abilities to inhibit neurotoxicity. The 4-(2-carbethoxyethanamino)- 7-chloro-3-nitroquinolin-2(1H)-one (9b) exhibited favorable NMDA receptor binding site activity and 7-chloro-4-(benzylamino)-3- nitroquinolin-2(1H)-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(1H)-ones.",

author = "Jung, \{Jae Chul\} and Seikwan Oh and Kim, \{Won Ki\} and Park, \{Woo Kyu\} and Kong, \{Jae Yang\} and Park, \{Oee Sook\}",

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T1 - Synthesis and biological properties of 4-substituted quinolin-2(1H)-one analogues

AU - Jung, Jae Chul

AU - Oh, Seikwan

AU - Kim, Won Ki

AU - Park, Woo Kyu

AU - Kong, Jae Yang

AU - Park, Oee Sook

PY - 2003

Y1 - 2003

N2 - A variety of 4-substituted quinolin-2(1H)-ones were prepared and evaluated for N-methyl-D-aspartate (NMDA) receptor binding site activity and their abilities to inhibit neurotoxicity. The 4-(2-carbethoxyethanamino)- 7-chloro-3-nitroquinolin-2(1H)-one (9b) exhibited favorable NMDA receptor binding site activity and 7-chloro-4-(benzylamino)-3- nitroquinolin-2(1H)-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(1H)-ones.

AB - A variety of 4-substituted quinolin-2(1H)-ones were prepared and evaluated for N-methyl-D-aspartate (NMDA) receptor binding site activity and their abilities to inhibit neurotoxicity. The 4-(2-carbethoxyethanamino)- 7-chloro-3-nitroquinolin-2(1H)-one (9b) exhibited favorable NMDA receptor binding site activity and 7-chloro-4-(benzylamino)-3- nitroquinolin-2(1H)-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(1H)-ones.

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DO - 10.1002/jhet.5570400410

M3 - Article

AN - SCOPUS:0141842657

SN - 0022-152X

VL - 40

SP - 617

EP - 623

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

IS - 4

ER -

Synthesis and biological properties of 4-substituted quinolin-2(1H)-one analogues

Abstract

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