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Bioorg Med Chem ; 20(2): 759-68, 2012 Jan 15.
Article in English | MEDLINE | ID: mdl-22202437

ABSTRACT

A facile and catalyst free synthesis of 6H-1-benzopyrano[4,3-b]quinolin-6-ones has been accomplished via the reaction of 4-chloro-2-oxo-2H-chromene-3-carbaldehyde with various aromatic amines in the presence of ultrasound. Some of these compounds were converted to the corresponding 2-(3-(hydroxymethyl)quinolin-2-yl)phenols and further structure elaboration of a representative quinoline derivative is presented. Molecular structure of two representative compounds was confirmed by single crystal X-ray diffraction study. Many of these compounds were evaluated for their anti-proliferative properties in vitro against four cancer cell lines and several compounds were found to be active. Further in vitro studies indicated that inhibition of sirtuins could be the possible mechanism of action of these molecules.


Subject(s)
Antineoplastic Agents/chemical synthesis , Benzopyrans/chemistry , Quinolines/chemistry , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Binding Sites , Catalysis , Catalytic Domain , Cell Line, Tumor , Computer Simulation , Crystallography, X-Ray , Drug Screening Assays, Antitumor , Humans , Molecular Conformation , Quinolines/chemical synthesis , Quinolines/pharmacology , Sirtuin 1/chemistry , Sonication
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