Bioactive Small Molecules Having a Fatty Residue. Part VI: Synthesis, Cytotoxicity Evaluation, and Molecular Docking Studies of New Pyrimidine Derivatives as Antitumor Agents

Difficultly accessible pyrimidine, thiazolopyrimidine, triazolopyrimidine, and thiazinopyrimidine derivatives containing an oleyl residue were synthesized via alkylation of 6-oleyl-2-thiouracil. The structure of the synthesized compounds was established on the basis of their spectral data, elemental...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2020-12, Vol.56 (12), p.2212-2221
Main Authors: Yakout, El-Sayed M. A., Salam, Hayam A. Abd El, Nawwar, Galal A. M.
Format: Article
Language:English
Subjects:
Alkylation
Anticancer properties
Biocompatibility
Biotechnology
Cancer
Chemical synthesis
Chemistry
Chemistry and Materials Science
Cytotoxicity
Derivatives
Molecular docking
Molecular dynamics
Organic Chemistry
Residues
Toxicity
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Summary:Difficultly accessible pyrimidine, thiazolopyrimidine, triazolopyrimidine, and thiazinopyrimidine derivatives containing an oleyl residue were synthesized via alkylation of 6-oleyl-2-thiouracil. The structure of the synthesized compounds was established on the basis of their spectral data, elemental analyses, and chemical behavior. The in vitro cytotoxicity of selected compounds was screened against two human cancer cell lines, MCF-7 breast cancer and HepG2 liver cancer cell lines. 8-[(8 Z )-Heptadec-8-en-1-yl)-3-hydroxy-3,4-dihydropyrimido[2,1- b ][1,3]thiazin-6(2 H )-one turned out to be the most potent with IC 50 values of 12.5 and 20 μg/mL against MCF-7 and HepG2 cancer cell lines, respectively. The structure–activity relationship for this compound was interpreted in terms of molecular docking and molecular dynamics studies.
ISSN:1070-4280
1608-3393
DOI:10.1134/S107042802012026X