title: [Enantioselective biotransformation of a new theophylline derivative].
abstract: Reductive amination of 4 with (RS)-2 is an improved method to obtain 7-((RS)2-((RS)-1-Methyl-2-phenyl-ethylamino)propyl)-theophylline (3) (ratio of diastereomers 1:1) compared with SN-displacement of proxyphyllintosylate with (RS)-2 (ratio of diastereomers 9:1). Due to steric hindrance 3 is no noteworthy prodrug for the intermediate formation of (RS)-2 in rats. The enantioselectivity of 2 after a single oral dose of 3 is determined in 24-h urine by HPLC on a Cyclobond-column using the isoindole derivatives, formed from o-phthalaldehyde, thioglycolic acid, and 2. The R(-)-amphetamine isomer is formed to a lesser amount (34.8%, range 32-37%) than the S(+)-isomer (65.2%, range 63-68%).
authors.affiliation: Institut für Pharmazeutische Chemie, Johann Wolfgang Goethe-Universität, Frankfurt am Main.
authors.forename: C
authors.initials: C
authors.lastname: Harsche
authors.forename: H
authors.initials: H
authors.lastname: Oelschläger
authors.forename: J
authors.initials: J
authors.lastname: Engel
mesh_terms: D000818:Animals; D001711:Biotransformation; D005260:Female; D051381:Rats; D017208:Rats, Wistar; D013237:Stereoisomerism; D013806:Theophylline / Q000031:analogs & derivatives* / Q000493:pharmacokinetics
chemical_list: C073108:7-(2-(1-methyl-2-phenyl-ethylamino)propyl)theophylline; D013806:Theophylline
vernacular_title: Enantioselektivität der Biotransformation eines neuen Theophyllinderivats.