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Paper | Regular issue | Vol 29, No. 8, 1989, pp.1497-1516
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4947
Design and Synthesis of 4-Oxoquinolin-2-yl-6-heptenoic Acid Derivatives as HMG-CoA Reductase Inhibitors

Gary M. Coppola,* Terrence J. Scallen, Ann DelPrete, and Rita Montano

*Sandoz Research Institute, Sandoz, Inc., Route 10, East Hanover, New Jersey 07936, U.S.A.

Abstract

Syntheses of two isomeric series of 4-oxoquinolin-2-yl-6-heptenoic acid derivatives 7 and 8 are described. The quinolinone portion of the molecules was constructed from the reaction of either an N-alkyl- or N-arylisatoic anhydride with an appropriate ketone enolate. The side-chain was elaborated by way of an aldol condensation using ethyl acetoacetate dianion fllowed by stereoselective ketone reduction. The N-aryl series 8 exhibited significantly greater inhibitory activity than the N-alkyl series 7.