Synthesis and biological activity of some 4-amino-3-cinnolinecarboxylic acid derivatives. Part 5: Pyrimido[5,4-c]cinnolines and triazepino[7,6-c]cinnoline.
A series of substituted 3-aminopyrimido[5,4-c]cinnolines 3, 7 was prepared. 6,7-Substituted 4-amino-3-cinnolinecarboxylic acid 1 were condensed with acetic anhydride to give the respective 1,3-oxazino[5,4-c]cinnolines 2. The obtained derivatives reacted with hydrazines and gave 3-aminopyrimido[5,4-c]cinnolines. Reaction of the esters 5 with hydrazines produced hydrazides 6, which upon treatment with N,N-dimethylformamide dimethyl acetal gave 3-aminopyrimido[5,4-c]cinnolines 7. Treatment of 6b with bromocyan produced 2-amino-3,4-dihydro-3,10-dimethyl-5 H-1,3,4-triazepino[7,6-c]cinnolin-5-on (8b). Some of the synthesized compounds were screened for their effect on the CNS.
Stańczak
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A
Department of Pharmaceutical Chemistry and Drug Analysis, Medical University of Lódź, Poland.
Ochocki
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Z
Pakulska
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W
D000818:Animals; D001381:Azepines / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D001763:Blepharoptosis / Q000139:chemically induced; D001831:Body Temperature / Q000187:drug effects; D002492:Central Nervous System Depressants / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D004347:Drug Interactions; D005260:Female; D007035:Hypothermia / Q000139:chemically induced; D007928:Lethal Dose 50; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D009043:Motor Activity / Q000187:drug effects; D011724:Pyridazines / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D051381:Rats; D017208:Rats, Wistar; D013055:Spectrophotometry, Infrared; D013239:Stereotyped Behavior / Q000187:drug effects
C118040:2-amino-3,4-dihydro-3,10-5H-1,3,4-triazepino(7,6-c)cinnolin-5-one; D001381:Azepines; D002492:Central Nervous System Depressants; D011724:Pyridazines; D011743:Pyrimidines