2-chloro-1-(5-(5-chloro-2-hydroxyphenyl)-3-methyl-4,5-dihydropyrazol-1-yl)ethanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-chloro-1-(5-(5-chloro-2-hydroxyphenyl)-3-methyl-4,5-dihydropyrazol-1-yl)ethanone
• 英文别名: 2-Chloro-1-[3-(5-chloro-2-hydroxyphenyl)-5-methyl-3,4-dihydropyrazol-2-yl]ethanone；2-chloro-1-[3-(5-chloro-2-hydroxyphenyl)-5-methyl-3,4-dihydropyrazol-2-yl]ethanone
• 化学式: C₁₂H₁₂Cl₂N₂O₂
• 分子量: 287.145
• InChiKey: PISFZLGBNDTOLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(5-chloro-2-hydroxyphenyl)but-3-en-2-one 在 4-二甲氨基吡啶 、 一水合肼 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 7.0h， 生成 2-chloro-1-(5-(5-chloro-2-hydroxyphenyl)-3-methyl-4,5-dihydropyrazol-1-yl)ethanone
  参考文献：
  名称：

  Identification of human telomerase inhibitors having the core of N -acyl-4,5-dihydropyrazole with anticancer effects

  摘要：

  Eight human telomerase inhibitors (5a-5h) having the core of N-acyl-4,5-dihydropyrazole with anticancer effects were identified in this study. Biological results revealed that a few compounds had potent anticancer activities against three common tumor cell lines (SGC-7901, HepG2 and MGC-803). Among them, compound 5c, with a molecular weight of only 272.2 Da, had antiproliferative activities against SGC-7901 and MGC-803 with EC50 values of 2.06 +/- 0.17 and 2.89 +/- 0.62 mu M, respectively, better than 5-Fluorouracil. Compound 5c inhibited the enzyme of telomerase with an IC50 value of 1.86 +/- 0.51 mu M, surpassing the control compound, ethidium bromide. Modeling study showed that this compound can reside in the binding pocket of the telomerase/TNA: DNA hairpin complex. When the moiety of N-acyl was changed to N-sulfonyl, the gotten compounds (8a-8i) had deteriorative activities against both these three cancer cell lines and the enzyme of telomerase. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.02.025

文献信息

• Identification of human telomerase inhibitors having the core of N -acyl-4,5-dihydropyrazole with anticancer effects
  作者：Xuan Xiao、Yong Ni、Ying-Ming Jia、Min Zheng、Han-Fei Xu、Jun Xu、Chenzhong Liao

  DOI：10.1016/j.bmcl.2016.02.025

  日期：2016.3

  Eight human telomerase inhibitors (5a-5h) having the core of N-acyl-4,5-dihydropyrazole with anticancer effects were identified in this study. Biological results revealed that a few compounds had potent anticancer activities against three common tumor cell lines (SGC-7901, HepG2 and MGC-803). Among them, compound 5c, with a molecular weight of only 272.2 Da, had antiproliferative activities against SGC-7901 and MGC-803 with EC50 values of 2.06 +/- 0.17 and 2.89 +/- 0.62 mu M, respectively, better than 5-Fluorouracil. Compound 5c inhibited the enzyme of telomerase with an IC50 value of 1.86 +/- 0.51 mu M, surpassing the control compound, ethidium bromide. Modeling study showed that this compound can reside in the binding pocket of the telomerase/TNA: DNA hairpin complex. When the moiety of N-acyl was changed to N-sulfonyl, the gotten compounds (8a-8i) had deteriorative activities against both these three cancer cell lines and the enzyme of telomerase. (C) 2016 Elsevier Ltd. All rights reserved.