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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

From: Synthesis of 4,4′-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) and evaluation of their antioxidant and anticancer activities

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
  1. aThe tests for significance were limited to ANOVA-Dunnett post-test, *p < 0.01, **p < 0.001, ***p < 0.0001 vs. 1
  2. bUsing 100% EtOH
  3. cUsing 60% EtOH
  4. dUsing 50% EtOH