Reference

The metabolic chiral inversion of 2-phenylpropionic acid in rat, mouse and rabbit

The metabolic chiral inversion of 2-phenylpropionic acid in rat, mouse and rabbit. Fournel, Sylvie; Caldwell, John (Med. Sch., St. Mary's Hosp., London W2 1PG, UK). Biochem. Pharmacol., 35(23), 4153-9 (English) 1986. CODEN: BCPCA6. ISSN: 0006-2952. DOCUMENT TYPE: Journal CA Section: 1 (Pharmacology) The metabolic chiral inversion of the 2-arylpropionic acids, which are an important class of anti-inflammatory drugs, was investigated in lab. animals, with the use of the simplest congener RS-2-phenylpropionic acid [2328-24-7] as a model compd. Chiral inversion was found to occur after administration of the racemate to the rat and rabbit, but not in the mouse. The formation of the ester glucuronide was enantioselective for the R-(-)-isomer [7782-26-5] in the rat and rabbit, but was preferential for the S-(+)-form [7782-24-3] in the mouse. In the rat, the extent of inversion from R-(-) to S-(+) was greater at a dose of 30 mg/kg than at 150 or 300 mg/kg. The enantiomeric compn. of the acid in urine was the same when the racemate was given orally or by i.p. injection. When the R-(-)isomer was given to rats, some 30% of the excreted acid was in the S-(+)-form, but when the S-(+)-isomer was given, the inversion was much less evident. In this case, the S/R ratio of the excreted phenylproprionic acid was approx. 9:1. Following the administration of the racemate to rats, the plasma elimination half-life of the R-(-)-form was shorter (3.0 vs 4.8 h for the S-(-)-isomer); this was due to its considerably greater plasma clearance (65.9 vs 43.6 mg/mL h), since the vols. of distribution of the enantiomers were the same. The S/R ratio of 2-phenylpropionic acid in plasma rose progressively with time, from 1:1 in the dose soln. to 2.1:1 at 8 h.

Resolution of (±)-2-phenylpropionic acid

Resolution of (±)-2-phenylpropionic acid. Nohira, Hiroyuki; Kumagai, Noriaki; Oonishi, Takashi (Kuraray Co, Japan). Jpn. Kokai Tokkyo Koho JP 08319252 A2 3 Dec 1996 Heisei, 5 pp. (Japanese). (Japan). CODEN: JKXXAF. CLASS: ICM: C07C057-30. ICS: C07B057-00; C07C051-487; C07M007-00. APPLICATION: JP 1995-149669 24 May 1995. DOCUMENT TYPE: Patent CA Section: 25 (Benzene, Its Derivatives, and Condensed Benzenoid Compounds) The process consists of treating (±)-2-phenylpropionic acid (I) with optically active 3-methyl-2-phenylbutylamine (II) as the resolving agent. A mixt. of 4.00 mmol (±)-I and 4.00 mmol (+)-II in H2O was treated at 90°, then crystd. at 20° to give (-)-I.(+)-II, which was treated with aq. NaOH to give 0. 186460-31-1 and 7782-26-5 which are cas registry numbers of substances are two of reagents here.94 mmol (-)-I of 99.3% e.e. .