Dapson in Heterocyclic Chemistry, Part V: Synthesis, Molecular Docking and Anticancer Activity of Some Novel Sulfonylbiscompounds Carrying Biologically Active Dihydropyridine, Dihydroisoquinoline, 1,3-Dithiolan, 1,3-Dithian, Acrylamide, Pyrazole, Pyrazolopyrimidine and Benzochromenemoieties
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Date
2012
Journal Title
Journal ISSN
Volume Title
Type
Article
Publisher
Chemical and Pharmaceutical Bulletin
Series Info
Chem. Pharm. Bull.;60 (8) 1019–1028
Doi
Scientific Journal Rankings
Abstract
N,N′-(4,4′-Sulfonylbis(4,1-phenylene))bis(2-cyanoacetamid) 2 was utilized as a key intermediate for the
synthesis of novel dihydropyridines 3, 4, 8, dihydroisoquinolines 5–7, dithiolan 10, dithian 11, acrylamide 12,
benzochromenes 17 and 18 and chromenopyridones 19 and 20. Compound 2 was the starting material in the
synthesis of the acrylamide derivative 14, the pyrazole derivative 15 and the pyrazolopyrimidine derivative
16. All the synthesized compounds were evaluated for their in vitro anticancer activity against human breast
cancer cell line (MCF7). Compound 19 showed the best cytotoxic activity with IC50 value 19.36 μM. In addition,
molecular docking study of the synthesized compounds on the active sites of farnesyltransferase and
arginine methyltransferase was performed in order to give a suggestion about the mechanism of action of
their cytotoxic activity.
Description
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Keywords
sulfone, pyridine, pyrazolopyrimidine, benzochromene, anticancer activity
Citation
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