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Different behavior toward racemization in basic media from chiral analogs of clofibric acid, the active metabolite of the antilipidemic drug clofibrate
Author(s) -
Ferorelli Savina,
Loiodice Fulvio,
Longo Antonio,
Molfetta Angelica,
Tortorella Vincenzo,
Amoroso Rosa
Publication year - 2000
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/1520-636x(2000)12:10<697::aid-chir1>3.0.co;2-l
Subject(s) - racemization , chemistry , clofibric acid , clofibrate , metabolite , stereochemistry , hydrochloride , intramolecular force , medicinal chemistry , organic chemistry , biochemistry
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 3α‐tropanol, whereas no racemization takes place with 3α‐tropanol as hydrochloride salt and with 3β‐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. Chirality 12:697–704, 2000. © 2000 Wiley‐Liss Inc.