Synthesis and preliminary pharmacological investigation of the central action of derivatives of 3-aminomethyl-5-(p-chlorophenyl)-tetrahydrofuran-2-one and 2-aminomethyl-4-(p-chlorophenyl)-4-hydroxybutyric acid.
Using 3-cyano-5-(p-chlorophenyl)-tetrahydrofuran-2-one 4, 3-aminomethyl derivatives of 5-(p-chlorophenyl)-tetrahydrofuran-2-one were synthesized. The starting material under alkaline hydrolysis yielded 5-(p-chlorophenyl)-tetrahydrofuran-2-one-3-carboxylic acid 5, which was transformed, via an acid chloride, into amide 6. From acid 5 by aminomethylation compounds 7-12 were obtained. Some of them (7, 8, 12) in reactions of ammono-, amino-, and hydrazinolysis yielded corresponding derivatives of 2-aminomethyl-4-(p-chlorophenyl)-4-hydroxybutyric acid 13-20. In pharmacological tests compounds 10 displayed analgesic activity while compounds 2 and 3 revealed anxiolytic properties.
Zabska
R
R
Department of Medicinal Chemistry, Medical Academy, Wroclaw, Poland.
Wilimowski
M
M
Barczyńska
J
J
Kedzierska-Goździk
L
L
Wojewódzki
W
W
Duś
E
E
Rutkowska
M
M
Szelag
A
A
D000700:Analgesics; D000818:Animals; D000927:Anticonvulsants; D001058:Apomorphine / Q000037:antagonists & inhibitors; D001794:Blood Pressure / Q000187:drug effects; D002492:Central Nervous System Depressants / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D005260:Female; D005663:Furans / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D010654:Phenylbutyrates / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D011919:Rats, Inbred Strains; D012110:Reserpine / Q000037:antagonists & inhibitors; D012640:Seizures / Q000517:prevention & control; D012702:Serotonin Antagonists; D013239:Stereotyped Behavior / Q000187:drug effects
D000700:Analgesics; D000927:Anticonvulsants; D002492:Central Nervous System Depressants; D005663:Furans; D010654:Phenylbutyrates; D012702:Serotonin Antagonists; C061761:3-aminomethyl-5-(4-chlorophenyl)-tetrahydrofuran-2-one; C061763:2-aminomethyl-4-(4-chlorophenyl)-4-hydroxybutyric acid; D012110:Reserpine; D001058:Apomorphine