5-(4-Chloro-phenyl)-2-[2-hydroxy-3-(4-nitro-phenoxy)-propyl]-2H-pyrazole-3-carboxylic acid ethyl ester | 918879-65-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-Chloro-phenyl)-2-[2-hydroxy-3-(4-nitro-phenoxy)-propyl]-2H-pyrazole-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 5-(4-chlorophenyl)-2-[2-hydroxy-3-(4-nitrophenoxy)propyl]pyrazole-3-carboxylate
• CAS: 918879-65-9
• 化学式: C₂₁H₂₀ClN₃O₆
• 分子量: 445.859
• InChiKey: GUHGHMKLFSSHBU-UHFFFAOYSA-N

物化性质

• 沸点：
  662.8±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(4-Chloro-phenyl)-2-[2-hydroxy-3-(4-nitro-phenoxy)-propyl]-2H-pyrazole-3-carboxylic acid ethyl ester 在 一水合肼 作用下， 以 甲醇 为溶剂， 以87%的产率得到3-(4'-chlorophenyl)-1-(2'-hydroxy-3'-(4'-nitrophenoxy)propyl)-1H-pyrazole-5-carbohydrazide
  参考文献：
  名称：

  合成和发现用于A549和H460肺癌细胞的自噬诱导剂，新型1-（2'-羟基-3'-芳氧基丙基）-3-芳基-1H-吡唑-5-碳酰肼衍生物。

  摘要：

  合成了一系列新型的1-（2'-羟基-3'-芳氧基丙基）-3-芳基-1H-吡唑-5-碳酰肼衍生物，并研究了这些化合物对A549细胞生长的影响。结果表明，所有的1-（2'-羟基-3'-芳氧基丙基）-3-芳基-1H-吡唑-5-碳酰肼衍生物2均可以剂量和时间依赖性的方式抑制A549细胞的生长。通常，化合物2a和2d诱导A549细胞自噬，但不会引起细胞凋亡和坏死，而2d在H460细胞中具有最大的自噬诱导作用。更重要的是，2a和2d不会抑制HUVEC细胞的生长。

  DOI：

  10.1016/j.bmcl.2008.06.058
• 作为产物：
  描述：

  4-(4-氯苯基)-2,4-二氧代丁酸乙酯 在 potassium carbonate 、 溶剂黄146 、 肼 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 5-(4-Chloro-phenyl)-2-[2-hydroxy-3-(4-nitro-phenoxy)-propyl]-2H-pyrazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Design, synthesis, and preliminary biological evaluation of novel ethyl 1-(2′-hydroxy-3′-aroxypropyl)-3-aryl-1H-pyrazole-5-carboxylate

  摘要：

  We synthesized a series of novel small molecules, ethyl 1-(2'-hydroxy-3'-aroxypropyl)-3-aryl-1H-pyrazole-5-carboxylate derivatives 3a-3o, by the reaction of ethyl 3-aryl-1H-pyrazole-5-carboxylate with 2-aryloxymethylepoxide in the presence of potassium carbonate at refluxing in acetonitrile in moderate or excellent yields. We investigated the effects of all the compounds on A549 cell growth. The results showed that 15 compounds could suppress A549 lung cancer cell growth. Among them, compound 3i was the most effective small molecule in inhibiting A549 cell growth. Compound 3f might most effectively induce A549 cell differentiation. Compound 3g remarkably induced cellular vacuolation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.008

文献信息

• Microwave‐Assisted Rapid and Straightforward Synthesis of Novel 6‐(Aroxymethyl)‐2‐aryl‐6,7‐dihydropyrazolo[5,1‐<i>c</i>][1,4]oxazin‐4‐one Derivatives
  作者：Fang Wei、Bao‐Xiang Zhao、Wen‐Liang Dong、Hua Zuo、Dong‐Soo Shin、Da‐Wei Wang、Yong Xia、Yan‐Qing Ge

  DOI：10.1080/00397910701577877

  日期：2007.11
• Design, synthesis, and preliminary biological evaluation of novel ethyl 1-(2′-hydroxy-3′-aroxypropyl)-3-aryl-1H-pyrazole-5-carboxylate
  作者：Fang Wei、Bao-Xiang Zhao、Bin Huang、Lu Zhang、Chun-Hui Sun、Wen-Liang Dong、Dong-Soo Shin、Jun-Ying Miao

  DOI：10.1016/j.bmcl.2006.09.008

  日期：2006.12

  We synthesized a series of novel small molecules, ethyl 1-(2'-hydroxy-3'-aroxypropyl)-3-aryl-1H-pyrazole-5-carboxylate derivatives 3a-3o, by the reaction of ethyl 3-aryl-1H-pyrazole-5-carboxylate with 2-aryloxymethylepoxide in the presence of potassium carbonate at refluxing in acetonitrile in moderate or excellent yields. We investigated the effects of all the compounds on A549 cell growth. The results showed that 15 compounds could suppress A549 lung cancer cell growth. Among them, compound 3i was the most effective small molecule in inhibiting A549 cell growth. Compound 3f might most effectively induce A549 cell differentiation. Compound 3g remarkably induced cellular vacuolation. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and discovery of autophagy inducers for A549 and H460 lung cancer cells, novel 1-(2′-hydroxy-3′-aroxypropyl)-3-aryl-1H-pyrazole-5-carbohydrazide derivatives
  作者：Chuan-Dong Fan、Bao-Xiang Zhao、Fang Wei、Gai-Hua Zhang、Wen-Liang Dong、Jun-Ying Miao

  DOI：10.1016/j.bmcl.2008.06.058

  日期：2008.7

  A series of novel 1-(2'-hydroxy-3'-aroxypropyl)-3-aryl-1H-pyrazole-5-carbohydrazide derivatives were synthesized, and the effects of the compounds on A549 cell growth were investigated. The results showed that all of the 1-(2'-hydroxy-3'-aroxypropyl)-3-aryl-1H-pyrazole-5-carbohydrazide derivatives 2 could inhibit the growth of A549 cells in dosage- and time-dependent manners. Typically, compound 2a

  合成了一系列新型的1-（2'-羟基-3'-芳氧基丙基）-3-芳基-1H-吡唑-5-碳酰肼衍生物，并研究了这些化合物对A549细胞生长的影响。结果表明，所有的1-（2'-羟基-3'-芳氧基丙基）-3-芳基-1H-吡唑-5-碳酰肼衍生物2均可以剂量和时间依赖性的方式抑制A549细胞的生长。通常，化合物2a和2d诱导A549细胞自噬，但不会引起细胞凋亡和坏死，而2d在H460细胞中具有最大的自噬诱导作用。更重要的是，2a和2d不会抑制HUVEC细胞的生长。