Synthesis of novel fatty acid 3,4-dihydropyrimidin-2-(1 H )-one and antitumoral activity against breast and gastric cancer cells

Synthesis of novel fatty acid 3,4-dihydropyrimidin-2-(1 H )-one and antitumoral activity against breast and gastric cancer cells

Monastrol is the best-known small compound from the dihydropyrimidinones/thiones (DHPMs) heterocycle family, a cell-permeable molecule recognized as an inhibitor of mitotic kinesin Eg5, that is over-expressed in tumor cells and is a very promising target for the development of new drugs for cancer....

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Published in:RSC advances Vol. 14; no. 32; pp. 22981 - 22987
Main Authors: Rios, E A M, Dea, C M, Dos Santos, E R F B, D'Oca, M G M, Rampon, D S, Nachtigall, F M, Santos, L S, Guzman, L, Moore-Carrasco, R, Rebolledo-Mira, D, D'Oca, C R M
Format: Journal Article
Language:English
Published: England Royal Society of Chemistry 19-07-2024
The Royal Society of Chemistry
Subjects:
Anticancer properties
Chemical synthesis
Chemistry
Gastric cancer
Hydroxybenzaldehydes
Sulfamic acid
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Summary:Monastrol is the best-known small compound from the dihydropyrimidinones/thiones (DHPMs) heterocycle family, a cell-permeable molecule recognized as an inhibitor of mitotic kinesin Eg5, that is over-expressed in tumor cells and is a very promising target for the development of new drugs for cancer. The lipophilic properties of the DHPMs have been demonstrated to be of pivotal importance in the design of new molecules. This work describes the synthesis and antitumoral activity of novel C5-substituted fatty-DHPMs against breast and gastric cancer cell lines. The compounds were synthesized Biginelli multicomponent reaction from oleyl β-ketoester in good yields (40-72%) using a simple approach catalyzed by nontoxic and free-metal sulfamic acid. Among the compounds tested, the compound 10c, derived from 3-hydroxybenzaldehyde and urea, exhibited 77% cellular viability to normal cells (C2C12) and was selected to be evaluated against tumoral breast (MCF-7) and gastric (AGS) cell lines. The results obtained afforded an IC of breast cancer cells of 2.3 μM, qualifying the molecule as the most potent, and making it a promising compound for future experiments .
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ISSN:2046-2069
2046-2069
DOI:10.1039/d4ra03292f