Ultrasound mediated catalyst free synthesis of 6H-1-benzopyrano[4,3-b]quinolin-6-ones leading to novel quinoline derivatives: their evaluation as potential anti-cancer agents.
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.
Institute of Life Sciences, University of Hyderabad Campus, Hyderabad 500 046, India.
Naveen
N
Mulakayala
D
D
Rambabu
Mohan Rao
MR
Raja
Chaitanya
C
M
Chitta Suresh
CS
Kumar
Arunasree M
AM
Kalle
G
G
Rama Krishna
C
C
Malla Reddy
M V
MV
Basaveswara Rao
Manojit
M
Pal
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001578:Benzopyrans / Q000737:chemistry*; D001665:Binding Sites; D002384:Catalysis; D020134:Catalytic Domain; D045744:Cell Line, Tumor; D003198:Computer Simulation; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008968:Molecular Conformation; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D056564:Sirtuin 1 / Q000737:chemistry; D013010:Sonication
D000970:Antineoplastic Agents; D001578:Benzopyrans; D011804:Quinolines; C037219:quinoline; C447939:SIRT1 protein, human; D056564:Sirtuin 1