Synthesis of novel tetrahydronaphthalen-2-yl heterocycles for analgesic, anti-inflammatory and antipyretic evaluation.
Condensation of 2-acetyltetralin with ethylcyanoacetate and/or malononitrile and some aldehydes in the presence of excess of ammonium acetate afforded the respective hydroxycyanopyridines or aminocyanopyridines 1a-f and 2a-f. Treatment of 2-acetyltetralin with some sulfonylhydrazides yielded the hydrazone derivatives 3a-d, respectively, which upon treatment with thioglycolic acid gave the corresponding thiazole derivatives 4a-d, respectively. Compounds 4a-d underwent cyclocondensation with different arylidene derivatives to give the corresponding pyrane derivatives 5a-d. Upon the reaction of compounds 4a-d with some secondary amines and paraformaldehyde the corresponding Mannich bases 6a,c, 7b,d and 8a,d were obtained. Compounds 1c, 1d, 1e, 2e, 3a and 3d were evaluated as analgesic, anti-iflammatory and antipyretic agents.
Fathalla
Omar Abd El-Fattah M
OA
Department of Medicinal Chemistry, National Research Centre, Dokki, Cairo, Egypt. omarfathalla@yahoo.com
Anwar
Manal M
MM
Haiba
Mogeda E
ME
Nofal
Salwa M
SM
D000700:Analgesics / Q000138:chemical synthesis / Q000494:pharmacology*; D018712:Analgesics, Non-Narcotic / Q000138:chemical synthesis / Q000494:pharmacology*; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D005260:Female; D005334:Fever / Q000188:drug therapy; D006571:Heterocyclic Compounds; D007213:Indomethacin / Q000494:pharmacology; D007249:Inflammation / Q000188:drug therapy; D008297:Male; D051379:Mice; D010146:Pain / Q000188:drug therapy; D051381:Rats; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis / Q000494:pharmacology*
D000700:Analgesics; D018712:Analgesics, Non-Narcotic; D000893:Anti-Inflammatory Agents; D006571:Heterocyclic Compounds; D013764:Tetrahydronaphthalenes; D007213:Indomethacin