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ID: ALA1140241

Journal: Bioorg Med Chem Lett

Title: Discovery of new diphenyloxazole derivatives containing a pyrrolidine ring: orally active prostacyclin mimetics. Part 2.

Authors: Hattori K, Okitsu O, Tabuchi S, Taniguchi K, Nishio M, Koyama S, Seki J, Sakane K.

Abstract: Synthetic and biological evaluation of novel diphenyloxazole derivatives containing a pyrrolidine ring, as a prostacyclin mimetic without the PG skeleton, are described. Asymmetric reduction of a ketone using a chiral Ru complex and reductive amination by NaBH(4) produces four isomers of the tetrahydronaphthalene ring and the pyrrolidine ring with high stereoselectivity. FR193262 (4), (R,R)-diphenyloxazolyl pyrrolidine derivative, displays high potency and agonist efficacy at the IP receptor and has good bioavailability in rats and dogs.

CiteXplore: 15935660

DOI: 10.1016/j.bmcl.2005.04.042