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

Dalian Zhao; Xu Feng; Cheng yi Chen; Rich D. Tillyer; Edward J.J. Grabowski; Paul J. Reider; Cameron Black; Nathalie Quimet; Peppi Prasit

doi:10.1016/S0040-4020(99)00274-4

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

Dalian Zhao
, Xu Feng
, Cheng yi Chen
, Rich D. Tillyer
, Edward J.J. Grabowski
, Paul J. Reider
, Cameron Black
, Nathalie Quimet
, Peppi Prasit

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

24 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	6001-6018
Number of pages	18
Journal	Tetrahedron
Volume	55
Issue number	19
DOIs	https://doi.org/10.1016/S0040-4020(99)00274-4
State	Published - May 7 1999
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Acylation
Alkylation
COX-II inhibitor
Suzuki coupling
Synthesis

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10.1016/S0040-4020(99)00274-4

Cite this

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title = "Efficient syntheses of 2-(3',5'-difluorophenyl)-3-(4'- methylsulfonylphenyl)-cyclopent-2-enone, a potent COX-2 inhibitor",

abstract = "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.",

keywords = "Acylation, Alkylation, COX-II inhibitor, Suzuki coupling, Synthesis",

author = "Dalian Zhao and Xu Feng and Chen, \{Cheng yi\} and Tillyer, \{Rich D.\} and Grabowski, \{Edward J.J.\} and Reider, \{Paul J.\} and Cameron Black and Nathalie Quimet and Peppi Prasit",

year = "1999",

month = may,

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doi = "10.1016/S0040-4020(99)00274-4",

language = "English (US)",

volume = "55",

pages = "6001--6018",

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TY - JOUR

T1 - Efficient syntheses of 2-(3',5'-difluorophenyl)-3-(4'- methylsulfonylphenyl)-cyclopent-2-enone, a potent COX-2 inhibitor

AU - Zhao, Dalian

AU - Feng, Xu

AU - Chen, Cheng yi

AU - Tillyer, Rich D.

AU - Grabowski, Edward J.J.

AU - Reider, Paul J.

AU - Black, Cameron

AU - Quimet, Nathalie

AU - Prasit, Peppi

PY - 1999/5/7

Y1 - 1999/5/7

N2 - 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.

AB - 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.

KW - Acylation

KW - Alkylation

KW - COX-II inhibitor

KW - Suzuki coupling

KW - Synthesis

UR - https://www.scopus.com/pages/publications/0033532012

UR - https://www.scopus.com/pages/publications/0033532012#tab=citedBy

U2 - 10.1016/S0040-4020(99)00274-4

DO - 10.1016/S0040-4020(99)00274-4

M3 - Article

AN - SCOPUS:0033532012

SN - 0040-4020

VL - 55

SP - 6001

EP - 6018

JO - Tetrahedron

JF - Tetrahedron

IS - 19

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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