3-(4-ethoxycarbonylphenyl)indazole | 886755-45-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-ethoxycarbonylphenyl)indazole
• 英文别名: ethyl 4-(1H-indazol-3-yl)benzoate
• CAS: 886755-45-9
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: VLXRWMJWZUFFNW-UHFFFAOYSA-N

物化性质

• 沸点：
  475.4±28.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-ethoxycarbonylphenyl)indazole 、 3-甲氧基氯苄 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以49.5%的产率得到Ethyl 4-[1-[(3-methoxyphenyl)methyl]indazol-3-yl]benzoate
  参考文献：
  名称：

  Synthesis and antiplatelet activity of ethyl 4-(1-benzyl-1H-indazol-3-yl)benzoate (YD-3) derivatives

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.10.070
• 作为产物：
  描述：

  (2-bromophenyl)(p-tolyl)methanol 在 copper(I) oxide 、 盐酸 、 ammonium cerium (IV) nitrate 、 四丁基氟化铵 、 硝酸 、 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醇 、 异戊醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 81.0h， 生成 3-(4-ethoxycarbonylphenyl)indazole
  参考文献：
  名称：

  铜（I）介导的邻卤代芳基N-甲苯磺酰hydr的环化反应：吲唑的高效合成

  摘要：

  从邻卤代芳基N-甲苯磺酰基hydr的易获得的E / Z混合物中开发了吲唑的有效合成方法。讨论了N-甲苯磺酰hydr的热诱导异构化。以高收率制备了一系列有价值的吲唑衍生物，该方法已成功地用于生物活性化合物的合成，如：lonidamine，AF-2785，axitinib，YC-1和YD-3。

  DOI：

  10.1002/adsc.201500953

文献信息

• Synthesis of N2 - (substituted arylmethyl) -3- (substituted phenyl) indazoles as novel anti-angiogenic agents
  申请人：Kuo Sheng-Chu

  公开号：US20060106032A1

  公开（公告）日：2006-05-18

  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。
• 一种吲唑的制备方法及其在药物合成中的应 用
  申请人：兰州大学

  公开号：CN106316958B

  公开（公告）日：2018-08-14

  本发明属于化学领域，涉及一种吲唑的制备方法及其在药物合成中的应用。本发明公开一种吲唑的制备方法及其在1H‑吲唑‑3‑羧酸、lonidamine、化合物8、化合物9、化合物10、axitinib、YD‑3、YC‑1及其类似物合成中的应用。
• Synthesis of N2-(substituted arylmethyl)-3-(substituted phenyl)indazoles as novel anti-angiogenic agents
  申请人：Yung Shin Pharm. Ind. Co., Ltd.

  公开号：US07514465B2

  公开（公告）日：2009-04-07

  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-吲唑啉和1-(取代芳基甲基)-3-(取代苯基)-1H-吲唑啉的新化合物，并且它们可用作抗血管生成剂。
• 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。
• Microwave-assisted synthesis of N-2-benzyl-3-(4-ethoxycarbonylphenyl)indazole derivatives
  作者：H CHEN、L HUANG、F WONG、F LEE、C TENG、S KUO

  DOI：10.1016/s0385-5414(07)81204-4

  日期：2007.12.1

  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.