Enantioselective synthesis and evaluation of 4-styryldihydropyrimidin-2-thiones as anti-proliferative agents

A series of novel chiral 4-styryldihydropyrimidin-2-thiones were prepared with high yields and enantioselective by a Biginelli reaction. In the condensation reaction, substituted cinnamaldehyde, thiourea, and β-ketoester were organocatalyzed to afford 4-styryldihydropyrimidin-2-thiones 4a – v using...

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Veröffentlicht in:Medicinal chemistry research 2017-04, Vol.26 (4), p.787-795
Hauptverfasser: Yu, Han, Dai, Guoyong, He, Qiu-Rui, Tang, Jiang-Jiang
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Sprache:eng
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Zusammenfassung:A series of novel chiral 4-styryldihydropyrimidin-2-thiones were prepared with high yields and enantioselective by a Biginelli reaction. In the condensation reaction, substituted cinnamaldehyde, thiourea, and β-ketoester were organocatalyzed to afford 4-styryldihydropyrimidin-2-thiones 4a – v using self-assembled methanoproline-thiourea as catalysts. Anti-proliferative activity of these 4-styryldihydropyrimidin-2-thiones was tested against the HepG2 and PC-3 cells. Among all the tested compounds, 4e , 4k , and 4s bearing CF 3 - groups at styryl group displayed moderate anti-proliferative activity with IC 50 ranged between 29.3–38.5 μM. The structure–activity relationship showed that substituents (R 1 ) on the C-4 styryl ring of 4-styryldihydropyrimidin-2-thiones and R 3 at ester group affected the anti-proliferative activity, yet R 2 at C-6 position had little influence for anti-proliferative activity.
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-017-1790-4