Efficient syntheses of 2-(3′,5′-difluorophenyl)-3-(4′-methylsulfonylphenyl)cyclopent-2-enone, a potent COX-2 inhibitor

Autor:	Nathalie Ouimet, Feng Xu, Cameron Black, Paul J. Reider, Edward J. J. Grabowski, Peppi Prasit, R. D. Tillyer, Dalian Zhao, Cheng-yi Chen
Rok vydání:	1999
Předmět:	Stereochemistry Organic Chemistry High selectivity Alkylation Biochemistry Acylation chemistry.chemical_compound Malonate chemistry Suzuki reaction Intramolecular force Drug Discovery COX-2 inhibitor Enone
Zdroj:	Tetrahedron. 55:6001-6018
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(99)00274-4
Popis:	2-(3′,5′-Difluorophenyl)-3-(4′-methylsulfonylphenyl)cyclopent-2-enone (1) displays high selectivity and potency against COX-2. Three efficient syntheses of this diarylcyclopentenone are described. The first approach employs a Suzuki coupling reaction as the key step while the second synthesis features an intramolecular Friedel-Crafts acylation. The third, and preferred route to this compound involves a sequential malonate alkylation and acylation and ring-closure sequence.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9e654e9402b1cf57eae1262f172dbf45 https://doi.org/10.1016/s0040-4020(99)00274-4 Zobrazit plný text záznamu Full Text from ScienceDirect