[Synthesis, biotransformation and pharmacodynamics of a new theophylline derivative].
7-[(RS)2-((S)-1-Methyl-2-phenyl-ethylamino)propyl]-theophylline (3) was not described until now. This fenetylline analogue is available by reaction of 7 with an excess of 2 at 150 degrees C. If 2 reacts with 4, an E2-elimination overwhelms SN-nucleophilic displacement yielding compound 5. In vivo studies with male White-Wistar rats, comparing biotransformation of 3 and 1, demonstrate, that the amount of 2 is decreased from 4.7% of (RS)-2 to 1%, probably due to steric hindrance of the attacking monooxygenases by the methyl group at C-11 of 3. Pharmacodynamic studies of 3, tested with mice, gave similar results to those obtained with 1.
Oelschläger
H
H
Institut für Pharmazeutische Chemie, Johann Wolfgang Goethe-Universität, Frankfurt am Main.
Harsche
C
C
Engel
J
J
D000818:Animals; D001711:Biotransformation; D008297:Male; D051379:Mice; D009043:Motor Activity / Q000187:drug effects; D051381:Rats; D011919:Rats, Inbred Strains; D013806:Theophylline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000493:pharmacokinetics / Q000494:pharmacology
C073108:7-(2-(1-methyl-2-phenyl-ethylamino)propyl)theophylline; D013806:Theophylline
Synthese, Biotransformation und Pharmakodynamik eines neuen Theophyllinderivats.