Title of article :
2-Imino 2H-chromene and 2-(phenylimino) 2H-chromene 3-aryl carboxamide derivatives as novel cytotoxic agents: synthesis, biological assay, and molecular docking study
Author/Authors :
Edraki, Najmeh Medicinal and Natural Products Chemistry Research Center - Shiraz University of Medical Sciences, Shiraz, Iran , Iraji, Aida Medicinal and Natural Products Chemistry Research Center - Shiraz University of Medical Sciences, Shiraz, Iran , Firuzi, Omidreza Medicinal and Natural Products Chemistry Research Center - Shiraz University of Medical Sciences, Shiraz, Iran , Fattahi, Yousef Department of Medicinal Chemistry - Faculty of Pharmacy, and Pharmaceutical Sciences Research Center - Tehran University of Medical Sciences, Tehran, Iran , Mahdavi, Mohammad Department of Medicinal Chemistry - Faculty of Pharmacy, and Pharmaceutical Sciences Research Center - Tehran University of Medical Sciences, Tehran, Iran , Foroumadi, Alireza Department of Medicinal Chemistry - Faculty of Pharmacy, and Pharmaceutical Sciences Research Center - Tehran University of Medical Sciences, Tehran, Iran , Khoshneviszadeh, Mehdi Medicinal and Natural Products Chemistry Research Center - Shiraz University of Medical Sciences, Shiraz, Iran , Shafiee, Abbas Department of Medicinal Chemistry - Faculty of Pharmacy, and Pharmaceutical Sciences Research Center - Tehran University of Medical Sciences, Tehran, Iran , Miri, Ramin Medicinal and Natural Products Chemistry Research Center - Shiraz University of Medical Sciences, Shiraz, Iran
Abstract :
The inhibition of AKR1B10 has been recognized as a potential therapeutic approach to the treatment of various types of cancers. A novel series of compounds with imino-2H-chromen and phenylimino-2H-chromen scaffolds were synthesized by Knoevenagel condensation reaction. The in vitro cytotoxic activity of synthesized compounds was evaluated against MOLT-4 and SK-OV-3 cells. Among the tested compounds, N-(3,4-dimethoxyphenyl)-2-(phenylimino)-2H-chromene-3-carboxamide (8g) demonstrated potent inhibitory activity against both examined cell lines. The results of the molecular docking study suggested that this compound is involved in critical hydrogen-bonding interactions with the Val301 and Lue302 of AKR1B10 catalytic site.
Keywords :
Cytotoxic agents , Iminochromene , Phenyliminochromene , AKR1B10 inhibitor , Knoevenagel condensation
