Synthesis of new nonclassical acridines, quinolines, and quinazolines derived from dimedone for biological evaluation.
New nonclassical acridines, quinolines, and quinazolines were prepared starting from cyclic β-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 µg/mL) than the other derivatives.
El-Sabbagh
Osama I
OI
Department of Medicinal Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig, Egypt. elsabbagh_59@yahoo.com
Shabaan
Mohamed A
MA
Kadry
Hanan H
HH
Al-Din
Ehab Saad
ES
D000166:Acridines / Q000138:chemical synthesis / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology; D003512:Cyclohexanones / Q000737:chemistry / Q000494:pharmacology; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D056945:Hep G2 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D008113:Liver Neoplasms / Q000188:drug therapy / Q000473:pathology; D008826:Microbial Sensitivity Tests; D011799:Quinazolines / Q000138:chemical synthesis / Q000494:pharmacology*; D011804:Quinolines / Q000138:chemical synthesis / Q000494:pharmacology*
D000166:Acridines; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D003512:Cyclohexanones; D011799:Quinazolines; D011804:Quinolines; C004774:dimedone