Antipyrine congeners as antidepressant agents.
1-(N-Antipyrinylglycyl)-3-arylideneamino)-2-thiobarbituric acids (III) were synthesized from 1-arylidene-4-(N-antipyrinyl glycyl)-3-thiosemicarbazones (II). Compounds II in turn were prepared from 4-amino antipyrine. Compounds III were finally converted into 1-(N-antipyrinylglycyl)-3-[(3'-chloro-4-aryl)azitidinyl]-2-t hiobarbituric acids (IV). 4-Aminoantipyrine was also treated with different N-protected amino acids in the presence of N,N'-dicyclohexylcarbodiimide to yield N-(antipyrinylcarbamoyl) substituted alkyl benzamides (V); their debenzoylation yielded 2-(amino-N-antipyrinyl) substituted acetamides (VI). The compounds were screened for their antidepressant activity. Compounds IIId, Va and Vb exhibited activity better than imipramine with less toxicity (ALD50 > 1000 mg/kg).
Tripathi
M
M
Department of Pharmacology and Therapeutics, King George's Medical College, Lucknow, India.
Verma
M
M
Palit
G
G
Shanker
K
K
D000661:Amphetamine / Q000494:pharmacology; D000818:Animals; D000928:Antidepressive Agents / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D000983:Antipyrine / Q000031:analogs & derivatives* / Q000494:pharmacology* / Q000633:toxicity; D001522:Behavior, Animal / Q000187:drug effects; D005260:Female; D007099:Imipramine / Q000494:pharmacology; D007928:Lethal Dose 50; D008297:Male; D051379:Mice; D009043:Motor Activity / Q000187:drug effects; D009422:Nervous System Diseases / Q000139:chemically induced / Q000503:physiopathology; D010862:Pilocarpine / Q000494:pharmacology; D012110:Reserpine / Q000037:antagonists & inhibitors / Q000494:pharmacology
D000928:Antidepressive Agents; D010862:Pilocarpine; D012110:Reserpine; D000661:Amphetamine; D007099:Imipramine; D000983:Antipyrine