2-methyl-6-(3-methyl-4,5-dihydro-1H-pyrazol-5-yl)phenol | 1310098-63-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-methyl-6-(3-methyl-4,5-dihydro-1H-pyrazol-5-yl)phenol
• CAS: 1310098-63-5
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: NWVLWGGNLRXQGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.62
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-methyl-6-(3-methyl-4,5-dihydro-1H-pyrazol-5-yl)phenol 、 苯甲酸 在 4-二甲氨基吡啶 、 对甲苯磺酰氯 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以54%的产率得到(5-(2-hydroxy-3-methylphenyl)-3-methyl-4,5-dihydropyrazol-1-yl)(phenyl)methanone
  参考文献：
  名称：

  Design and synthesis of N-phenylacetyl (sulfonyl) 4,5-dihydropyrazole derivatives as potential antitumor agents

  摘要：

  A series of novel N-phenylacetyl (sulfonyl) 4,5-dihydropyrazole derivatives as potential telomerase inhibitors were synthesized. The bioassay tests show that compound 4a exhibited high activity against human gastric cancer cell SGC-7901, liver cancer Hep-G2 and human prostate PC-3 cell lines with IC50 values of 21.23 +/- 0.99, 29.43 +/- 0.32 and 30.89 +/- 1.07 mu M, respectively. All title compounds were assayed for telomerase inhibition by a modified TRAP assay, the results show that compound 4a can inhibit telomerase with IC50 value of 4.0 +/- 0.32 mu M. Docking simulation was performed to position compound 4a into the telomerase (3DU6) active site to determine the probable binding model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.066
• 作为产物：
  描述：

  2-羟基-3-甲基苯甲醛 在 一水合肼 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 17.0h， 生成 2-methyl-6-(3-methyl-4,5-dihydro-1H-pyrazol-5-yl)phenol
  参考文献：
  名称：

  Design and synthesis of N-phenylacetyl (sulfonyl) 4,5-dihydropyrazole derivatives as potential antitumor agents

  摘要：

  A series of novel N-phenylacetyl (sulfonyl) 4,5-dihydropyrazole derivatives as potential telomerase inhibitors were synthesized. The bioassay tests show that compound 4a exhibited high activity against human gastric cancer cell SGC-7901, liver cancer Hep-G2 and human prostate PC-3 cell lines with IC50 values of 21.23 +/- 0.99, 29.43 +/- 0.32 and 30.89 +/- 1.07 mu M, respectively. All title compounds were assayed for telomerase inhibition by a modified TRAP assay, the results show that compound 4a can inhibit telomerase with IC50 value of 4.0 +/- 0.32 mu M. Docking simulation was performed to position compound 4a into the telomerase (3DU6) active site to determine the probable binding model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.066