Synthesis and antiulcer activity of optical isomers of 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic acid (Rebamipide)

DOI: 10.1248/cpb.39.2906

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 2906 - 2909 (1991)

Update date:2022-08-05

Topics:

Authors:

Otsubo Otsubo

Morita Morita

Uchida Uchida

Yamasaki

Kanbe Kanbe

Shimizu Shimizu

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Article abstract of DOI:10.1248/cpb.39.2906

The enantiomers of 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic acid [(±)-1, rebamipide, OPC-12759], a new antiulcer agent that enhances mucosal resistance, were synthesized from optically active α-amino acid derivatives of 2(1H)-quinolinone. The key intermediates, α-amino acid derivatives, were prepared by asymmetric synthesis and optical resolution. The (±)-1 was ahout 1.7 times as potent as the (-)-isomer in antiulcer activity against ethanol-induced gastric ulcers.

Full text of DOI:10.1248/cpb.39.2906

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