212126-32-4Relevant academic research and scientific papers
A three-component coupling approach to cyclopentanoids
Trost,Pinkerton
, p. 7714 - 7722 (2007/10/03)
A new approach to 2,3-disubstituted cyclopentenones has been developed. This approach consists of a two-step protocol involving the cyclization of a Z-vinyl bromide under Barbier type conditions to form a cyclopentenol, which is then oxidatively rearranged to generate the cyclopentenone. The Z-vinyl bromide is in turn derived from a ruthenium catalyzed three-component coupling of an alkyne, an enone, and a HBr equivalent. A range of 2,3-disubstituted cyclopentenones has been generated, including short syntheses of jasmone and dihydrojasmone. Further applicability of this strategy is shown in the total syntheses of tetrahydrodicranenone B, rosaprostol, and a selective COX-2 inhibitor.
Enhanced geometrical control in a Ru-catalyzed three component coupling
Trost,Pinkerton
, p. 9627 - 9631 (2007/10/03)
Exclusive Z-selectivity in the Ru-catalyzed bromoalkylation of alkynes with vinyl ketones is observed with aryl and other tertiary substituted acetylenic substrates, a feature that has led to an efficient synthesis of a COX-2 inhibitor. (C) 2000 Elsevier
Efficient syntheses of 2-(3',5'-difluorophenyl)-3-(4'- methylsulfonylphenyl)-cyclopent-2-enone, a potent COX-2 inhibitor
Zhao, Dalian,Feng, Xu,Chen, Cheng-yi,Tillyer, Rich D.,Grabowski, Edward J. J.,Reider, Paul J.,Black, Cameron,Quimet, Nathalie,Prasit, Peppi
, p. 6001 - 6018 (2007/10/03)
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.
2,3-diarylcyclopentenones as orally active, highly selective cyclooxygenase-2 inhibitors
Black, W. Cameron,Brideau, Christine,Chan, Chi-Chung,Charleson, Stella,Chauret, Nathalie,Claveau, David,Ethier, Diane,Gordon, Robert,Greig, Gillian,Guay, Jocelyne,Hughes, Gregory,Jolicoeur, Paule,Leblanc, Yves,Nicoll-Griffith, Deborah,Ouimet, Nathalie,Riendeau, Denis,Visco, Denise,Wang, Zhaoyin,Xu, Lijing,Prasit, Petpiboon
, p. 1274 - 1281 (2007/10/03)
Cyclopentenones containing a 4-(methylsulfonyl)phenyl group in the 3- position and a phenyl ring in the 2-position are selective inhibitors of cyclooxygenase-2 (COX-2). The selectivity for COX-2 over COX-1 is dramatically improved by substituting the 2-phenyl group with halogens in the meta position or by replacing the phenyl ring with a 2- or 3-pyridyl ring. Thus the 3,5-difluorophenyl derivative 7 (L-776,967) and the 3-pyridyl derivative 13 (L-784,506) are particularly interesting as potential antiinflammatory agents with reduced side-effect profiles. Both exhibit good oral bioavailability and are potent in standard models of pain, fever, and inflammation yet have a much reduced effect on the GI integrity of rats compared to standard nonsteroidal antiflammatory drugs.
2-(3,5-difluorophenyl)-3-(4-(methyl-sulfonyl)phenyl)-2-cyclopenten-1-one useful as an inhibitor of cyclooxygenase-2
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, (2008/06/13)
The invention encompasses the novel compound A, 2-(3,5-difluorophenyl)-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one, pharmaceutical compositions and use of the compound in the preparation of medicaments for the treatment of cyclooxygenase-2 mediated diseases.
3,4-diaryl-2-hydroxy-2,5-dihydrofurans as prodrugs to COX-2 inhibitors
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, (2008/06/13)
The invention encompasses the novel compound of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases. STR1 The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.
