174088-06-3Relevant academic research and scientific papers
Synthesis and pharmacological activity of benzodipyran derivatives
Hishmat,El-Diwani,Melek,El-Sahrawi,El-Shabrawi
, p. 30 - 35 (2007/10/03)
3-Formyl-2-hydroxy-4-methoxy-7-methyl[1]benzopyran-5(H)-one (2), obtained by oxidation of 4-methoxy-7-methyl-furo[3,2-g][1]benzopyran-5(H)-one 1, on treatment with urea and thiourea in ethanol in the presence of anhydrous potassium carbonate gives 2,3-dihydroisoxazole derivatives 3a,b. Also, the reaction of 2 with aminoacetophenone, acetophenone and khellinone yield the chalcones 4a,b and 5 respectively. Reduction of the chalcones 4a,b and 5 with NaBH4 afford benzodipyran derivatives 6a,b and 7 respectively. Reaction of 4a,b with malononitrile, cyanoacetamide, 2-cyanoacetic acid hydrazide and 2-cyanomethylbenzimidazole in ethanol in the presence of triethylamine furnishes 2H, 6H-benzo[1,2-b; 4,5-b′]dipyran derivatives 8a-d and 8h-k, 8a-c on acid hydrolysis give 8e-g. Compounds 4b, 5, 6b, 7 and 8b,c have been tested for analgesic, antiinflammatory and ulcerogenic activities. Compounds 6b, 7 and 8b,c are found to be potent analgesics with minimal ulcerogenic effect except 6b. None of the compounds tested possesses antiinflammatory activity.
