title: Different behavior toward racemization in basic media from chiral analogs of clofibric acid, the active metabolite of the antilipidemic drug clofibrate.
abstract: Some chiral analogs of clofibric acid, the active metabolite of the antilipidemic drug clofibrate, show different configurational stability in basic conditions. Also, extensive racemization occurs when the corresponding optically active acid chlorides are treated with 3 alpha-tropanol, whereas no racemization takes place with 3 alpha-tropanol as hydrochloride salt and with 3 beta-tropanol and 1-methyl-4-hydroxy-piperidine as either the free base or hydrochloride salt. For these aminoalcohols, experimental evidence supports the hypothesis that a ketene intermediate is involved in the racemization process. Formation of intramolecular hydrogen bond is evoked to explain the different ability of aminoalcohols to induce ketene formation and consequent racemization.
authors.affiliation: Dipartimento Farmaco-Chimico, Facoltà di Farmacia, Università degli Studi di Bari, Bari, Italy.
authors.forename: S
authors.initials: S
authors.lastname: Ferorelli
authors.forename: F
authors.initials: F
authors.lastname: Loiodice
authors.forename: A
authors.initials: A
authors.lastname: Longo
authors.forename: A
authors.initials: A
authors.lastname: Molfetta
authors.forename: V
authors.initials: V
authors.lastname: Tortorella
authors.forename: R
authors.initials: R
authors.lastname: Amoroso
mesh_terms: D002994:Clofibrate / Q000737:chemistry; D002995:Clofibric Acid / Q000031:analogs & derivatives* / Q000737:chemistry*; D004952:Esters; D006868:Hydrolysis; D000960:Hypolipidemic Agents / Q000737:chemistry; D007202:Indicators and Reagents; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D004952:Esters; D000960:Hypolipidemic Agents; D007202:Indicators and Reagents; D002995:Clofibric Acid; D002994:Clofibrate