5-氰基-1H-吲哚-3-丙酸 | 149681-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 5-氰基-1H-吲哚-3-丙酸
• 英文名称: 5-cyanoindole-3-propionic acid
• 英文别名: 3-(5-cyano-1H-indol-3-yl)propanoic Acid
• CAS: 149681-66-3
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: AKWJKNNOUSXOMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  496.7±30.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  76.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氰基-1H-吲哚-3-丙酸 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 叔丁醇 为溶剂， 反应 9.0h， 以40.5%的产率得到3-(2-aminoethyl)-1H-indole-5-carbonitrile
  参考文献：
  名称：

  A New Synthesis of the Potent 5-HT₁Receptor Ligand, 5-Carboxyamidotryptamine (5-CT)

  摘要：

  A short, convenient and relatively efficient synthesis of 5-CT is developed through a modified Michael reaction. This method represents a new general synthesis for tryptamines with labile indole substituents.

  DOI：

  10.1080/00397919308018587
• 作为产物：
  描述：

  5-溴吲哚 在 N-甲基吡咯烷酮 、 乙酸酐 、 溶剂黄146 作用下， 反应 19.5h， 生成 5-氰基-1H-吲哚-3-丙酸
  参考文献：
  名称：

  A New Synthesis of the Potent 5-HT₁Receptor Ligand, 5-Carboxyamidotryptamine (5-CT)

  摘要：

  A short, convenient and relatively efficient synthesis of 5-CT is developed through a modified Michael reaction. This method represents a new general synthesis for tryptamines with labile indole substituents.

  DOI：

  10.1080/00397919308018587

文献信息

• Synthesis of CF₃-Containing Spirocyclic Indolines via a Red-Light-Mediated Trifluoromethylation/Dearomatization Cascade
  作者：Liangyong Mei、Jules Moutet、Savannah M. Stull、Thomas L. Gianetti

  DOI：10.1021/acs.joc.1c01313

  日期：2021.8.6

  Umemoto’s reagent has been developed. This protocol provides a facile and efficient approach for the construction of functionalized and potentially biologically important CF3-containing 3,3-spirocyclic indolines with moderate to high yields and excellent diastereoselectivities under mild conditions. The success of multiple gram-scale (1 and 10 g) experiments further highlights the robustness and practicality

  已经开发了红光介导的n Pr-DMQA +催化级联分子内三氟甲基化和吲哚衍生物与 Umemoto 试剂的脱芳构化。该协议为构建功能化且具有潜在生物学重要性的 CF 3 3,3-螺环二氢吲哚提供了一种简便有效的方法，在温和条件下具有中等至高产率和优异的非对映选择性。多个克级 (1 和 10 g) 实验的成功进一步突出了该协议的稳健性和实用性以及使用红光的优点。机理研究支持形成关键的 CF 3自由基物种和脱芳基苄基碳正离子中间体。
• [EN] TACRINE DERIVATIVES AS INHIBITORS OF ACETYLCHOLINESTERASE<br/>[FR] DERIVES DE TACRINE UTILISES EN TANT QU'INHIBITEURS DE L'ACETYLCHOLINESTERASE
  申请人：NEUROPHARMA SA

  公开号：WO2005005413A1

  公开（公告）日：2005-01-20

  The invention provides compounds of formula: (I) which have a tacrine moiety connected to an heterocyclic moiety through a linker. Through careful selection of the substituents and the linker, the activity and selectivity towards acetylcholinesterase can be modulated. The compounds show potent AChE inhibition activities together with modifications in the beta-amyloid aggregation properties by binding simultaneously to the catalytic and peripheral AChE sites. They are useful in the treatment of AChE mediated diseases, such as the Alzheimer's disease.

  该发明提供了具有以下公式的化合物：（I），其中通过连接剂将一种他环境基团连接到一种杂环基团。通过精心选择取代基和连接剂，可以调节对乙酰胆碱酯酶的活性和选择性。这些化合物显示出强大的AChE抑制活性，同时通过同时结合催化和外周AChE位点，改变了β-淀粉样蛋白聚集特性。它们在治疗AChE介导的疾病，如阿尔茨海默病中非常有用。
• Acetylcholinesterase dual inhibitors
  申请人：Gil Martinez Ana

  公开号：US20050148621A1

  公开（公告）日：2005-07-07

  The invention provides compounds of formula: which have a tacrine moiety connected to an heterocyclic moiety through a linker. Through careful selection of the substituents and the linker, the activity and selectivity towards acetylcholinesterase can be modulated. The compounds show potent AChE inhibition activities together with modifications in the β-amyloid aggregation properties by binding simultaneously to the catalytic and peripheral AChE sites. They are useful in the treatment of AChE mediated diseases, such as the Alzheimer's disease.

  该发明提供了公式的化合物：其中通过连接剂连接了一种Tacrine基团和一个杂环基团。通过精心选择取代基和连接剂，可以调节对乙酰胆碱酯酶的活性和选择性。这些化合物显示出强大的AChE抑制活性，同时通过同时结合催化和周围AChE位点，修改β淀粉样聚集物的聚集特性。它们在治疗AChE介导的疾病，如阿尔茨海默病中很有用。
• Amidinoindoles, amidinoazoles, and analogs thereof
  申请人：E. I. du Pont de Nemours and Company

  公开号：US06043257A1

  公开（公告）日：2000-03-28

  The present application describes amidinoindoles, amidinoazoles, and analogs thereof of formula I: ##STR1## wherein W, W.sup.1, W.sup.2, and W.sup.3 are selected from CH and N, provided that one of W.sup.1 and W.sup.2 is C(C(.dbd.NH)NH.sub.2) and at most two of W, W.sup.1, W.sup.2, and W.sup.3 are N and one of J.sup.a and J.sup.b is substituted by --(CH.sub.2).sub.n --Z--A--B, which are useful as inhibitors of factor Xa or thrombin.

  本申请描述了公式I的氨基亚硝基吲哚，氨基咪唑及其类似物：##STR1## 其中W，W.sup.1，W.sup.2和W.sup.3从CH和N中选择，前提是W.sup.1和W.sup.2中的一个是C(C(.dbd.NH)NH.sub.2)，并且W、W.sup.1、W.sup.2和W.sup.3中最多有两个是N，J.sup.a和J.sup.b中的一个被替换为--(CH.sub.2).sub.n --Z--A--B，这些化合物可用作因子Xa或凝血酶的抑制剂。
• ACETYLCHOLINESTERASE DUAL INHIBITORS
  申请人：Gil Ana Martinez

  公开号：US20110144148A1

  公开（公告）日：2011-06-16

  The invention provides compounds of formula: which have a tacrine moiety connected to an heterocyclic moiety through a linker. Through careful selection of the substituents and the linker, the activity and selectivity towards acetylcholinesterase can be modulated. The compounds show potent AChE inhibition activities together with modifications in the β-amyloid aggregation properties by binding simultaneously to the catalytic and peripheral AChE sites. They are useful in the treatment of AChE mediated diseases, such as the Alzheimer's disease.

  本发明提供了公式如下的化合物: 通过连接剂将Tacrine基团连接到杂环基团上。通过对取代基和连接剂的精心选择，可以调节其对乙酰胆碱酯酶的活性和选择性。这些化合物表现出强效的AChE抑制活性，并通过同时结合催化和周边AChE位点来改变β-淀粉样聚集物的聚集特性。它们在治疗AChE介导的疾病，如阿尔茨海默病方面非常有用。