N-2-benzyl-3-(4-ethoxycarbonylphenyl)indazole | 886755-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-2-benzyl-3-(4-ethoxycarbonylphenyl)indazole
• 英文别名: Ethyl 4-(2-benzyl-2H-indazol-3-yl)benzoate；ethyl 4-(2-benzylindazol-3-yl)benzoate
• CAS: 886755-47-1
• 化学式: C₂₃H₂₀N₂O₂
• 分子量: 356.424
• InChiKey: XKZXAIOXAYGVMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-2-benzyl-3-(4-ethoxycarbonylphenyl)indazole 在 calcium borohydride 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以76.9%的产率得到[4-(2-Benzyl-2H-indazol-3-yl)phenyl]methanol
  参考文献：
  名称：

  Synthesis of N2 - (substituted arylmethyl) -3- (substituted phenyl) indazoles as novel anti-angiogenic agents

  摘要：

  合成了2-(取代芳基甲基)-3-(取代苯基)-2H-吲唑并1-(取代芳基甲基)-3-(取代苯基)-1H-吲唑的新化合物，可作为抗血管生成抑制剂。

  公开号：

  US20060106032A1
• 作为产物：
  描述：

  3-(4-ethoxycarbonylphenyl)indazole 、 氯化苄 在 三乙胺 作用下， 反应 1.0h， 以51%的产率得到N-2-benzyl-3-(4-ethoxycarbonylphenyl)indazole
  参考文献：
  名称：

  Microwave-assisted synthesis of N-2-benzyl-3-(4-ethoxycarbonylphenyl)indazole derivatives

  摘要：

  The microwave-assisted synthesis for promoting N-2 substituted indazoles as the major products were successfully developed by treating 3-(4-ethoxycarbonylphenyl)indazoles with various substituted benzyl chloride (benzyl, o-chlorobenzyl, m-chlorobenzyl, and p-chlorobenzyl chloride) in the presence of two equivalents of triethylamine. The result was better than two trandional methods including the directly substitution with benzyl chloride and Mitsunobu reaction with benzyl alcohol.

  DOI：

  10.1016/s0385-5414(07)81204-4

文献信息

• Synthesis of substituted 2H-indazole derivatives as anti-angiogenic agents
  申请人：Yung Shin Pharm. Ind. Co., Ltd.

  公开号：EP1659115A1

  公开（公告）日：2006-05-24

  Novel compounds of 2-(substituted arylmethyl)-3-(substituted phenyl)-2H-indazoles and 1-(substituted arylmethyl)-3-(substituted phenyl)-1H-indazoles are synthesized, and useful as anti-angiogenic agents.

  合成了 2-(取代芳基甲基)-3-(取代苯基)-2H-吲唑和 1-(取代芳基甲基)-3-(取代苯基)-1H-吲唑的新型化合物，并将其用作抗血管生成剂。
• Synthesis and antiplatelet activity of ethyl 4-(1-benzyl-1H-indazol-3-yl)benzoate (YD-3) derivatives
  作者：Hua-Sin Chen、Sheng-Chu Kuo、Che-Ming Teng、Fang-Yu Lee、Jih-Pyang Wang、Yu-Chun Lee、Chiung-Wen Kuo、Ching-Che Huang、Chin-Chung Wu、Li-Jiau Huang

  DOI：10.1016/j.bmc.2007.10.070

  日期：2008.2.1

  Previously, ethyl 4-(1-benzyl-1H-indazol-3-yl)benzoate (YD-3) was identified by us as the first non-peptide protease-activated receptor 4 (PAR4) antagonist. To continue on our development of novel anti-PAR4 agents, YD-3 was used as a lead compound and a series of its derivatives were synthesized and evaluated for their selective anti-PAR4 activity. Through structure-activity relationship (SAR) study, we identified the important functional groups contributing to anti-PAR4 activity, and these functional groups were kept intact during subsequent structural modification. Several new compounds with anti-PAR4 activity comparable to YD-3 were identified. Among them, ethyl 4-[1-(3-chlorobenzyl)-1H-indazol-3-yl]benzoate (33) showed the most potent inhibitory effect on PAR4-mediated platelet aggregation, ATP release, and P-selectin expression. On the other hand, ethyl 4-(1-phenyl-1H-indazol-3-yl)benzoate (83) exhibited dual inhibitory effects on PAR4 and thromboxane formation from arachidonic acid. The above findings can be used as guidelines for development of novel antiplatelet drug candidates. (c) 2008 Published by Elsevier Ltd.
• US7514465B2
  申请人：——

  公开号：US7514465B2

  公开（公告）日：2009-04-07