5-苄氧基-1H-吲唑-3-甲醛 | 885271-28-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 5-苄氧基-1H-吲唑-3-甲醛
• 中文别名: 5-(苄氧基)-3-醛基吲唑
• 英文名称: 5-(benzyloxy)-1H-indazole-3-carbaldehyde
• 英文别名: 5-Benzyloxy-1H-indazole-3-carbaldehyde；5-phenylmethoxy-2H-indazole-3-carbaldehyde
• CAS: 885271-28-3
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: LSVWVZRXSDJJFU-UHFFFAOYSA-N

物化性质

• 沸点：
  485.9±30.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-苄氧基-1H-吲唑-3-甲醛 在 盐酸羟胺 、 氧气 、 copper diacetate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 5-(benzyloxy)-1-(4-(trifluoromethyl)phenyl)-1H-indazole-3-carbaldehyde oxime
  参考文献：
  名称：

  Indoles, Indazoles, and Related Analogs for Inhibiting YAP/TAZ-TEAD

  摘要：

  The present disclosure relates to novel compounds, to said compounds for use as a medicine, more in particular for the prevention or treatment of diseases mediated by activity of YAP/TAZ-TEAD transcription, yet more in particular for the prevention or treatment of cancer or fibrosis. The present disclosure also relates to a method for the prevention or treatment of said diseases comprising the use of the novel compounds.

  公开号：

  US20230202985A1
• 作为产物：
  描述：

  5-苄氧基吲哚 在 盐酸 、 水 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以91%的产率得到5-苄氧基-1H-吲唑-3-甲醛
  参考文献：
  名称：

  通过吲哚的亚硝化直接获得 1H-吲唑-3-甲醛衍生物的优化程序†

  摘要：

  吲唑衍生物目前作为激酶抑制剂在药物化学中越来越受到关注。1 H-吲唑-3-甲醛是获得多种多官能化3-取代吲唑的关键中间体。我们在这里报告了对这个基序的一般访问，基于在微酸性环境中吲哚的亚硝化。这些非常温和的条件允许富电子和缺电子吲哚转化为 1 H-吲唑-3-甲醛。

  DOI：

  10.1039/c8ra01546e

文献信息

• 3-Benzimidazol-2-yl-1H-indazoles as potent c-ABL inhibitors
  作者：Christopher M. McBride、Paul A. Renhowe、Thomas G. Gesner、Johanna M. Jansen、Julie Lin、Sylvia Ma、Yasheen Zhou、Cynthia M. Shafer

  DOI：10.1016/j.bmcl.2006.04.043

  日期：2006.7

  The 3-benzimidazol-2-yl-1H-indazole scaffold was developed as an alternate scaffold for our receptor tyrosine kinase (RTK) inhibitor program. In exploring the SAR of this series, it was discovered that a subset of these compounds potently inhibit the enzyme c-ABL. The SAR of these compounds is described. (c) 2006 Elsevier Ltd. All rights reserved.
• Design and structure–activity relationship of 3-benzimidazol-2-yl-1H-indazoles as inhibitors of receptor tyrosine kinases
  作者：Christopher M. McBride、Paul A. Renhowe、Carla Heise、Johanna M. Jansen、Gena Lapointe、Sylvia Ma、Ramon Piñeda、Jayesh Vora、Marion Wiesmann、Cynthia M. Shafer

  DOI：10.1016/j.bmcl.2006.03.069

  日期：2006.7

  -3-Benzimidazol-2-yl-1H-indazole analogs were developed as inhibitors of receptor tyrosine kinases (RTK). The synthesis and SAR of this series is reported. (c) 2006 Elsevier Ltd. All rights reserved.
• An optimized procedure for direct access to 1<i>H</i>-indazole-3-carboxaldehyde derivatives by nitrosation of indoles
  作者：Arnaud Chevalier、Abdelaaziz Ouahrouch、Alexandre Arnaud、Thibault Gallavardin、Xavier Franck

  DOI：10.1039/c8ra01546e

  日期：——

  Indazole derivatives are currently drawing more and more attention in medicinal chemistry as kinase inhibitors. 1H-indazole-3-carboxaldehydes are key intermediates to access to a variety of polyfunctionalized 3-substituted indazoles. We report here a general access to this motif, based on the nitrosation of indoles in a slightly acidic environment. These very mild conditions allow the conversion of

  吲唑衍生物目前作为激酶抑制剂在药物化学中越来越受到关注。1 H-吲唑-3-甲醛是获得多种多官能化3-取代吲唑的关键中间体。我们在这里报告了对这个基序的一般访问，基于在微酸性环境中吲哚的亚硝化。这些非常温和的条件允许富电子和缺电子吲哚转化为 1 H-吲唑-3-甲醛。
• Indoles, Indazoles, and Related Analogs for Inhibiting YAP/TAZ-TEAD
  申请人：THE KATHOLIEKE UNIVERSITEIT LEUVEN

  公开号：US20230202985A1

  公开（公告）日：2023-06-29

  The present disclosure relates to novel compounds, to said compounds for use as a medicine, more in particular for the prevention or treatment of diseases mediated by activity of YAP/TAZ-TEAD transcription, yet more in particular for the prevention or treatment of cancer or fibrosis. The present disclosure also relates to a method for the prevention or treatment of said diseases comprising the use of the novel compounds.