Table 1.
Inhibitory effect of the derivatives of chalcone 21 on melanin production in α-MSH-stimulated B16F10 cells. B16F10 cells were incubated for 3 days with each compound in the presence of α-MSH (10 nM) and data are expressed as mean ±SD based on three independent experiments (n = 3).
| Compound | Substitutions | Inhibition (%) at 3 μM | Viability (%) at 3 μM | IC50 (μM) | ||
|---|---|---|---|---|---|---|
| R1 | R2 | R3 | ||||
| Chalcone 21 | cyclohexylmethoxy | OH | CH2OH | 41.7 ± 3.3 | 95.1 ± 3.9 | >3.0 |
| 21-1 | 4-trifluoromethoxybenzyloxy | OH | CH2CH3 | 26.3 ± 6.5 | 79.7 ± 3.9 | >3.0 |
| 21-2 | 4-trifluoromethoxybenzyloxy | OH | Cl | 73.9 ± 6.8 | 60.6 ± 3.2 | 1.2 |
| 21-3 | 4-trifluoromethoxybenzyloxy | OH | OCH3 | 47.2 ± 7.8 | 78.6 ± 2.7 | >3.0 |
| 21-4 | 4-trifluoromethoxybenzyloxy | OH | COOH | 38.8 ± 6.2 | 78.9 ± 2.1 | >3.0 |
| 21-5 | 4-trifluoromethoxybenzyloxy | OH | NHCOCH3 | 89.4 ± 8.4 | 76.5 ± 3.1 | 0.88 |
| 21-6 | benzyloxy | OH | CH2CH3 | 42.8 ± 7.1 | 85.0 ± 4.6 | >3.0 |
| 21-7 | benzyloxy | OH | Cl | 65.0 ± 4.9 | 59.8 ± 3.9 | 2.3 |
| 21-8 | benzyloxy | OH | OCH3 | 35.7 ± 4.6 | 74.4 ± 3.1 | >3.0 |
| 21-9 | benzyloxy | OH | COOH | 55.8 ± 6.2 | 72.9 ± 2.2 | 2.6 |
| 21-10 | benzyloxy | H | CH2CH3 | 36.6 ± 5.6 | 77.0 ± 2.6 | >3.0 |
| 21-11 | benzyloxy | H | Cl | 72.0 ± 7.0 | 67.8 ± 3.5 | 2.0 |
| 21-12 | benzyloxy | H | OCH3 | 35.7 ± 5.8 | 81.6 ± 3.5 | >3.0 |
| 21-13 | benzyloxy | H | COOH | 91.8 ± 6.4 | 71.2 ± 2.8 | 1.6 |
| 21-14 | benzyloxy | H | NHCOCH3 | 47.1 ± 6.4 | 74.5 ± 3.8 | >3.0 |
| 21-15 | OH | H | CH2CH3 | 23.8 ± 4.9 | 78.3 ± 2.9 | >3.0 |
| 21-16 | OH | H | OCH3 | 21.6 ± 6.1 | 80.4 ± 3.0 | >3.0 |
| 21-17 | OH | H | NHCOCH3 | 9.4 ± 5.4 | 81.8 ± 4.8 | >3.0 |
| 21-18 | cyclohexylmethoxy | H | CH2CH3 | 29.1 ± 4.9 | 87.6 ± 4.2 | >3.0 |
| 21-19 | cyclohexylmethoxy | H | Cl | 49.7 ± 7.7 | 76.4 ± 3.6 | >3.0 |
| 21-20 | cyclohexylmethoxy | H | COOH | 19.8 ± 8.5 | 90.2 ± 3.2 | >3.0 |
| 21-21 | cyclohexylmethoxy | H | NHCOCH3 | 92.0 ± 5.5 | 86.3 ± 2.5 | 0.54 |