Syntheses and Structure−Activity Relationships of 5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-quinoxaline Derivatives with Retinoic Acid Receptor α Agonistic Activity

In the course of our studies on retinoic acid receptor (RAR) agonists, we have designed and synthesized a series of quinoxaline derivatives. One of them, 4-[5-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-quinoxalinyl)-1H-2-pyrrolyl]benzoic acid (3a), which possesses a 2,5-disubstituted pyrrole moiety,...

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Bibliographic Details
Published in:Journal of medicinal chemistry 2000-02, Vol.43 (3), p.409-419
Main Authors: Kikuchi, Kouichi, Hibi, Shigeki, Yoshimura, Hiroyuki, Tokuhara, Naoki, Tai, Kenji, Hida, Takayuki, Yamauchi, Toshihiko, Nagai, Mitsuo
Format: Article
Language:English
Subjects:
Antineoplastic agents
Benzoates - chemical synthesis
Benzoates - chemistry
Benzoates - metabolism
Benzoates - pharmacology
Binding, Competitive
Biological and medical sciences
Cell Differentiation - drug effects
Cell Line
General aspects
Humans
Medical sciences
Pharmacology. Drug treatments
Quinoxalines - chemical synthesis
Quinoxalines - chemistry
Quinoxalines - metabolism
Quinoxalines - pharmacology
Receptors, Retinoic Acid - agonists
Receptors, Retinoic Acid - metabolism
Retinoic Acid Receptor alpha
Retinoids - chemical synthesis
Retinoids - chemistry
Retinoids - metabolism
Retinoids - pharmacology
Structure-Activity Relationship
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Summary:In the course of our studies on retinoic acid receptor (RAR) agonists, we have designed and synthesized a series of quinoxaline derivatives. One of them, 4-[5-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-quinoxalinyl)-1H-2-pyrrolyl]benzoic acid (3a), which possesses a 2,5-disubstituted pyrrole moiety, showed selectivity for the RARα receptor and exerted highly potent cell-differentiating activity on HL-60 cells.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm990063w