Synthesis and pharmaceutical activity of new series of chromonyl derivatives.
A new synthesis of chromonyl based on the reaction of formylfurochromone (4,9-dimethoxy-5-oxo-5H-furo[3,2-g][1] benzopyran-6-carbaldebyde) 1 with semicarbazide hydrochloride and thiosemicarbazide afforded 4,9-dimethoxy-5-oxo-5H-furo[3,2-gl]][1] benzopyran-6-yl-(1-aminovinyl) hydrazone derivatives 2a,b. Also 4,5-Diphenyl-2-(4,9-dimethoxy-5-oxo-5H-furo[3,2-g][1] benzopyran-6-yl)-imidazole 3 was obtained by refluxing compound 1 with 1,2-diketone in presence of ammonium acetate. Reaction of compound 1 with different amines afforded 3-(4,9-dimethoxy-5-axo-5H-furo[3,2-g][1] benzopyran-6-yl)-aryliminoethyl derivatives 4a-g. Condensation reaction of compounds 4a-d to C-Hacid compounds were given 4-aminosubstituted-5-(6-hydroxy-4,7-dimethoxy-5-axo-5H- benzofuranyl)-pyrano[2,3-b] cyclobexa-2,3-diene 5a-d and 2-methyl-3-methoxy-4-(4-methoxypheny-lamine)-5-(6-hydroxy-4,7- dimethoxy-5-oxo-5H-benzofuranyl) 6. Refluxing compound 4d with thiosemicarbazide formed 6-methanimine-(4,9-dimethoxy-5-axo-5H-furo[3,2-g][1] benzopyran-6-yl)-(1E)-1-phenylethan-1-one thiosemicarbazide 7. Also, the reaction of compound 4d with p-aminoacetophenone gave the aryliminoethyl compound 8. The reaction of compound 4d with different aldehydes were given 3-(4,9-dimethoxy-5-oxo-5H-furo[3,2-g][1] benzopyran)-iminomethyl-(1-aryl-1-oxo-3-proponyl substituted) 9a-d. Condensation of formyl fuorochromone 1 with phenolic compounds yielded 3-(4,9-dimethoxy-5-axo-5H-furo[3,2-g][1] benzopyran-6-yl)-derivatives 10a-d. All the tested compounds a significant increase in PT & APTT when compared with that of the control group. Only the compound IIa treated rats induced significant increase Ast, alkaline phosphatase and urea during experimental period, while other tested compounds did not cause any significant changes in liver and kidney function. Concomitantly, all the tested compound caused a significant decrease in serum cholesterol and triglyceride levels.
Fawzy
N M
NM
Swelam
S A
SA
Batran
S A
SA
D000818:Animals; D000925:Anticoagulants / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D005260:Female; D006835:Hydrazones / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D007202:Indicators and Reagents; D007928:Lethal Dose 50; D008055:Lipids / Q000097:blood; D008111:Liver Function Tests; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D010314:Partial Thromboplastin Time; D011517:Prothrombin Time; D051381:Rats; D017207:Rats, Sprague-Dawley; D013055:Spectrophotometry, Infrared
D000925:Anticoagulants; D001578:Benzopyrans; D006835:Hydrazones; D007202:Indicators and Reagents; D008055:Lipids