Synthesis of D,L beta-aminomethyl derivatives of gamma-(p-chlorophenyl)-tetrahydrofuran-2-one.
Several new D,L beta-aminomethyl derivatives of gamma-(p-chlorophenyl)-tetrahydrofuran-2-one have been synthesized. The derivatives of D,L beta-aminomethyl-beta-(p-chlorobenzoyl)-propionic acid 2-6 were used as the substrates. These compounds were obtained by the Mannich reaction from acid 1, cyclic secondary amines and formaldehyde. After the reduction with NaBH4, and cyclization, derivatives 2-6 were converted into the appropriate derivatives of tetrahydrofuran-2-one 9-13. Some of the obtained compounds (5, 6, 8, 11 and 12) showed depressant activity against the central nervous system.
D000818:Animals; D002492:Central Nervous System Depressants / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D004295:Dihydroxyphenylalanine / Q000494:pharmacology; D004347:Drug Interactions; D005663:Furans / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D007928:Lethal Dose 50; D051379:Mice; D009043:Motor Activity / Q000187:drug effects; D010433:Pentylenetetrazole / Q000037:antagonists & inhibitors
D002492:Central Nervous System Depressants; D005663:Furans; D004295:Dihydroxyphenylalanine; D010433:Pentylenetetrazole