Table 2.
Anti-HCV activities and cytotoxic effects of quercetin-3-O-substituted derivatives.
| Compound | R1 | R2 | EC50(μM) a,b,c | CC50(μM) c,d | SI e | |
|---|---|---|---|---|---|---|
| Position | Substituent | |||||
| 4a | - | H | - | 14.3 ± 5.1 | >50 | >3.5 |
| 4b | 2'' | F | - | 12.9 ± 3.2 | >50 | >3.9 |
| 4c | NH2 | - | 12.8 ± 2.8 | >50 | >3.9 | |
| 4d | OCH3 | - | 11.7 ± 1.3 | >50 | >4.3 | |
| 4e | CN | - | 20.2 ± 8.6 | >50 | >2.5 | |
| 4f | 3'' | F | - | 9.0 ± 4.5 | >50 | >5.6 |
| 4g | NH2 | - | 21.1 ± 1.3 | >50 | >2.4 | |
| 4h | OCH3 | - | 15.6 ± 0.3 | >50 | >3.2 | |
| 4i | CN | - | 13.1 ± 1.0 | >50 | >3.8 | |
| 4j | Cl | - | 23.0 ± 3.2 | >50 | >3.5 | |
| 4k | 4'' | F | - | 9.7 ± 3.1 | 35.0 ± 2.4 | 3.6 |
| 4l | NH2 | - | 23.8 ± 0.8 | >50 | >2.1 | |
| 4m | OCH3 | - | 13.6 ± 2.1 | 33.9 ± 3.7 | 2.5 | |
| 4n | CN | - | 11.4 ± 2.3 | >50 | >4.4 | |
| 4o | Cl | - | 14.3 ± 2.2 | >50 | >3.5 | |
| 12a | - | - | Me | 11.2 ± 0.1 | >50 | >4.5 |
| 12b | - | - | i-Pr | 38.9 ± 2.5 | 28.8 ± 2.0 | 0.7 |
| 12c | - | - | (CH2)2OH | 26.3 ± 3.1 | >50 | >1.9 |
| 12d | - | - | (CH2)3CN | >50 | >50 | NA |
| 2 | quercetin | 19.8 | >50 | >2.5 | ||
a The anti-HCV assay was evaluated in an authentic HCV infection system in the human hepatoma cell lines, Huh7.5.1; b Concentration required to inhibit HCV RNA replication by 50%; c The values obtained as the average of duplicate determinations; d Concentration required to reduce cell proliferation by 50%; e Selectivity index: ratio of CC50 to EC50.