Table 1 Preparation of 4,4ʹ-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) derivatives 3a-q catalyzed by 10% NaOAc at room temperature, DPPH scavenging activity and cytotoxic activity against RKO cell line
Compounds | Time (min) | Yield (%) | Mp (°C) | DPPH scavenging activity IC50 (µM)a | Cytotoxic activity IC50 (µM) |
|---|---|---|---|---|---|
3a | 10 | 98 | 219.5–220.6 | 17.1 ± 2.5 | 143.0 ± 4.9 |
3b | 60 | 97 | 159.5–161.1 | 14.0 ± 2.3 | 105.9 ± 1.5 |
3c | 10 | 95 | 210.0–211.0 | 20.9 ± 5.9 | 34.1 ± 4.4 |
3d | 10 | 95b | 150.7–152.0 | 16.6 ± 1.1 | 46.7 ± 3.3 |
3e | 10 | Quant | 178.0–179.0 | 13.8 ± 0.7 | 36.3 ± 1.0 |
3f | 480 | 98c | 165.0–167.0 | 19.2 ± 1.5 | 84.3 ± 1.0 |
3g | 40 | 99 | 202.0–204.0 | 18.7 ± 1.6 | 23.5 ± 5.9 |
3h | 180 | 91c | 200.0–202.0 | 13.7 ± 4.0 | 97.5 ± 3.0 |
3i | 180 | 93d | 182.7–184.0 | 6.2 ± 0.6*** | 9.9 ± 1.1 |
3j | 180 | 97c | 217.2–218.9 | 17.8 ± 3.7 | 77.8 ± 1.1 |
3k | 120 | 92 | 176.0–177.0 | 19.7 ± 3.2 | 89.9 ± 3.0 |
3l | 20 | 97 | 218.0–219.0 | 18.8 ± 3.8 | 27.3 ± 1.1 |
3m | 60 | 87 | 183.8–185.8 | 10.2 ± 0.3 | 46.4 ± 1.0 |
3n | 10 | Quant | 217.2–218.7 | 10.8 ± 0.3 | 36.0 ± 1.0 |
3o | 15 | 96 | 203.0–205.0 | 9.8 ± 1.0* | 23.6 ± 1.0 |
3p | 60 | Quant | 174.5–176.0 | 12.3 ± 0.9 | 14.8 ± 1.0 |
3q | 15 | 60 | 209.1–211.3 | 13.0 ± 1.0 | 40.9 ± 1.0 |
Doxorubicin | – | – | – | – | 2.23 ± 0.02 |
1 | – | – | – | 18.1 ± 0.5 | – |
Ascorbic acid | – | – | – | 14.0 ± 2.3 | – |