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 |
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Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
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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. |
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ISSN: | 1054-2523 1554-8120 |
DOI: | 10.1007/s00044-017-1790-4 |