SYNTHESIS, ANTIMICROBIAL AND ANTIVIRAL ACTIVITY OF 1,8- DIOXODECAHYDROACRIDINE DERIVATIVES

Document Type : Original Article

Author

Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Zagazig University, Zagazig, Egypt.

Abstract

10-(4-Hdroxy phenyl)-9-4-substituted phenyl)-1,8-dioxo-1.2.3.4,5,6,7,8,9,10-decahydroacridine and  their 3,3,6,6,-tetramethyl derivatives (II1-4) have been prepared by reacting 3-(4-hydroxypheny lamino)-2-cyclohexenone or its 5,5-dimethyl derivative (I1,2 ) with the appropriate araldehyde. Alkylation of II1-4 with ethyl bromoacetate gave the corresponding esters III1-4 which were condensed with hydrazine hydrate to produce hydrazides IV1-4 .These hydrazides underwent condensation with either 2.5-hevanedione to afford the pyrrole derivatives V1-4, or aromatic aldehydes to give the hydrazone derivatives VI 1-20. Cyclo-condensation of some of the obtained hydrazones VI1,3,5,11-13,15-18 with thioglycolic acid afforded the corresponding thiazelidinones VII1-10 .The antimicrobial activity for thirteen new compounds against either Gram positive or negative bacteria and fungi showed that compounds IV were the most active ones against Bacillus subtilus Moreover, the antiviral activity for twenty Compound  performed on Vero cells against Rinderpest virus revealed that compounds IV3 , VI13 and VII6, caused reduction the cytopathic effect of virus: by 25, 33 and 50 %, respectively at a dose of 1000 µg/ml.