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Synthesis of New Nonclassical Acridines, Quinolines, and Quinazolines Derived from Dimedone for Biological Evaluation
Author(s) -
Sabbagh Osama I. El,
Shabaan Mohamed A.,
Kadry Hanan H.,
AlDin Ehab Saad
Publication year - 2010
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200900296
Subject(s) - dimedone , moiety , chemistry , stereochemistry , cytotoxic t cell , acridine , mtt assay , antimicrobial , quinazoline , combinatorial chemistry , organic chemistry , biochemistry , cell growth , in vitro , catalysis
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.