Design, synthesis and evaluation of novel tetrahydropyridothienopyrimidin-ureas as cytotoxic and anti-angiogenic agents

Author:

Motahari Rasoul,Boshagh Mohammad Amin,Moghimi Setareh,Peytam Fariba,Hasanvand Zaman,Oghabi Bakhshaiesh Tayebeh,Foroumadi Roham,Bijanzadeh Hamidreza,Firoozpour Loghman,Khalaj Ali,Esmaeili Rezvan,Foroumadi Alireza

Abstract

AbstractThe novel derivatives of tetrahydropyridothienopyrimidine-based compounds have been designed and efficiently synthesized with good yields through seven steps reaction. The anticancer activity of compounds 11a-y has been evaluated against MCF-7, PC-3, HEPG-2, SW-480, and HUVEC cell lines by MTT assay. The target compounds showed IC50 values between 2.81–29.6 μg/mL and were compared with sorafenib as a reference drug. Among them, compound 11n showed high cytotoxic activity against four out of five examined cell lines and was 14 times more selective against MRC5. The flow cytometric analysis confirmed the induction of apoptotic cell death by this compound against HUVEC and MCF-7 cells. In addition, 11n caused sub-G1 phase arrest in the cell cycle arrest. Besides, this compound induced anti-angiogenesis in CAM assay and increased the level of caspase-3 by 5.2 fold. The western-blot analysis of the most active compound, 11n, revealed the inhibition of VEGFR-2 phosphorylation. Molecular docking study also showed the important interactions for compound 11n.

Funder

Tehran University of Medical Sciences and Health Services

National Institute for Medical Research Development

Publisher

Springer Science and Business Media LLC

Subject

Multidisciplinary

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