Table 31.
Four-component synthesis and in vitro anticancer activity of 4,5-dihydropyrano[2,3-c]pyrazol-6(2H)-one derivatives 108.
| |||||
|---|---|---|---|---|---|
| Compound | R | Yield 108 (%) | IC50 (μM) | ||
| A2780 | MCF-7 | PC-3 | |||
| 108a | 3-MeO | 66 | 150 | 165 | 90 |
| 108b | 4-MeO | 65 | 150 | NA | 165 |
| 108c | 2,3-(MeO)2 | 60 | 150 | 120 | 100 |
| 108d | 2-OH-4-MeO | 80 | NA b | NA | NA |
| 108e | 2,4-(OH)2 | 85 | 150 | NA | 75 |
| 108f | 2,4-(MeO)2 | 68 | NA | 101 | NA |
| 108g | 2,5-(MeO)2 | 74 | 104 | 87 | 60 |
| 108h | 3,4-(MeO)2 | 75 | 150 | NA | 50 |
| 108i | 3,5-(MeO)2 | 70 | NA | 23 | 31 |
| 108j | 2,3,4-(OH)3 | 80 | NA | NA | NA |
| 108k | 2,3,4-(MeO)3 | 60 | NA | NA | NA |
| 108l | 3,4,5-(MeO)3 | 59 | NA | NA | NA |
| Doxorubicin a | -- | -- | 3.70 | 4.76 | 5.25 |
a Standard drug for the study. b NA = not active.