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Synthesis of New Nonclassical Acridines, Quinolines, and Quinazolines Derived from Dimedone for Biological Evaluation
Faculty
Pharmacy
Year:
2010
Type of Publication:
Article
Pages:
519-527
Authors:
El-Sabbagh, Osama I, Shabaan, Mohamed A, Kadry, Hanan H, Al-Din, Ehab Saad
DOI:
10.1002/ardp.200900296
Journal:
ARCHIV DER PHARMAZIE WILEY-BLACKWELL
Volume:
343
Research Area:
Pharmacology \& Pharmacy; Chemistry
ISSN
ISI:000282793400004
Keywords :
Acridines, Antimicrobial, Cytotoxic activity, Quinolines, Quinazolines
Abstract:
New nonclassical acridines, quinolines, and quinazolines were prepared starting from cyclic beta-diketones, namely dimedone, through application of Hantzsch addition, Michael addition, and Mannich reactions, respectively. The antimicrobial activity revealed that decahydroacridin-1,8-dione 2e bearing a 3-nitrophenyl group and hexahydroquinoline 4e having a 2,4-dichlorophenyl moiety were the most active compounds against both Gram-positive and -negative bacteria based upon using the disc diffusion method. Cytotoxic activity studies for decahydroacridin-1,8-diones 2a-e against liver carcinoma cells (HepG(2)) using the MTT cell viability assay revealed that decahydroacridin-1,8-dione bearing a 4-methylphenyl moiety 2d showed a higher cytotoxic activity (IC(50) - 4.42 mu g/mL) than the other derivatives.
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