Journal
JOURNAL OF HETEROCYCLIC CHEMISTRY
Volume 58, Issue 2, Pages 636-645Publisher
WILEY
DOI: 10.1002/jhet.4204
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In this study, tetrahydropyrimidinone derivative was synthesized through one-pot three components condensation and utilized for the construction of valuable N-heterocycles. The synthesized compounds exhibited significant antiproliferative activity against four human carcinoma cell lines and displayed selective cytotoxicity towards cancer cells through aquaporin channels, as confirmed by DFT simulation.
Tetrahydropyrimidinone derivative was synthesized through one-pot three components condensation of 1,3-diphenylpyrazole-4-carbaldehyde with pentan-2,4-dione and urea under Biginelli reaction conditions. The corresponding chloro- and hydrazino derivatives were synthesized and utilized for the construction of some valuable N-heterocycles encompassing both pyrazole and pyrimidine cores, such as triazolopyrimidine, tetrazolopyrimidine, pyrazole, and pyrazolone derivatives through condensation with nitrogen nucleophiles and carbon electrophiles. The antiproliferative activity evaluation of the synthesized compounds against four human carcinoma cell lines namely, liver carcinoma (HepG2), breast adenocarcinoma (MCF7), prostate cancer (PC3), and colon cancer (HCT-116) cell lines revealed that some of them provided significant potency, as well as the density-functional theory (DFT) was studied. The permeability of various hydrophilic and hydrophobic synthesized compounds across both normal and cancer cells is confirmed via DFT simulation in which the much higher permeability through aquaporin channels revealed the selective cytotoxicity toward cancer cells.
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