5-硝基吲哚-3-乙腈 | 6952-13-2

• 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-硝基吲哚-3-乙腈
• 中文别名: 5-硝基-3-吲哚乙腈
• 英文名称: 2-(5-nitro-1H-indol-3-yl)acetonitrile
• 英文别名: (5-nitro-1H-indol-3-yl)-acetonitrile；5-nitroindole-3-acetonitrile；(5-nitro-indol-3-yl)-acetonitrile；(5-Nitro-indol-3-yl)-acetonitril；<5-Nitro-indolyl-(3)>-acetonitril；3-Cyanomethyl-5-nitro-indol
• CAS: 6952-13-2
• 化学式: C₁₀H₇N₃O₂
• mdl: MFCD04972094
• 分子量: 201.184
• InChiKey: BAYBZUUQTBZGPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  187-189°C
• 溶解度：
  可溶于氯仿、二氯甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  85.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-硝基吲哚-3-乙腈 在 盐酸 作用下， 生成 (5-硝基-吲哚-3-基)-乙酸
  参考文献：
  名称：

  Cavallini; Ravenna, Farmaco, Edizione Scientifica, 1958, vol. 13, p. 105,109

  摘要：

  DOI：
• 作为产物：
  描述：

  5-硝基吲哚 在 溶剂黄146 、 碘甲烷 作用下， 以 乙醇 、 水 为溶剂， 反应 32.0h， 生成 5-硝基吲哚-3-乙腈
  参考文献：
  名称：

  Discovery of the cancer cell selective dual acting anti-cancer agent (Z)-2-(1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile (A131)

  摘要：

  Selective targeting of cancer cells over normal cells is a key objective of targeted therapy. However few approaches achieve true mechanistic selectivity resulting in debilitating side effects and dose limitation. In this work we describe the discovery of A131 (4a), a new agent with an unprecedented dual mechanism of action targeting both mitosis and autophagy. Compound 4a was first identified in a phenotypic screen in which HeLa cells treated with 4a manifested mitotic arrest along with formation of multiple vesicles. Further investigations showed that 4a causes an increase in mitotic marker pH3 and autophagy marker LC3. Importantly 4a induces cell death in cancer cells while sparing normal cells which regrow after 4a is removed. Dual activities against pH3 and LC3 markers are required for cancer cell selectivity. An extensive SAR investigation confirmed 4a as the optimal dual inhibitor with potency against a panel of 30 cancer cell lines (average antiproliferative GI(50) 1.5 mu M). In a mouse model of paclitaxel-resistant colon cancer, 4a showed 74% tumor growth inhibition when administered at a dose of 20 mg/kg IP twice a day. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.07.011

文献信息

• Use of derivatives of indoles for the treatment of cancer
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US09212138B2

  公开（公告）日：2015-12-15

  The present invention relates to the use of derivatives of indoles having a general formula (I) as follow: for the manufacture of a pharmaceutical composition intended for the treatment of cancer.

  本发明涉及使用具有以下一般式(I)的吲哚衍生物制备用于治疗癌症的药物组合物。
• [EN] N-(2-ARYLETHYL)BENZYLAMINES AS ANTAGONISTS OF THE 5-HT6 RECEPTOR<br/>[FR] N-(2-ARYLETHYL)BENZYLAMINES UTILISEES EN TANT QU'ANTAGONISTES DU RECEPTEUR 5-HT6
  申请人：LILLY CO ELI

  公开号：WO2002078693A2

  公开（公告）日：2002-10-10

  The present invention provides compounds of formula (I), which are antagonists of the 5-HT6 receptor.

  本发明提供了式（I）的化合物，它们是5-HT6受体的拮抗剂。
• N-(2-arylethyl) benzylamines as antagonists of the 5-ht6 receptor
  申请人：Chen Zhaogen

  公开号：US20060009511A9

  公开（公告）日：2006-01-12

  The present invention provides compounds of formula (I), which are antagonists of the 5-HT 6 receptor.

  本发明提供了式(I)的化合物，它们是5-HT6受体的拮抗剂。
• 3-aminoalkyl-1H-indole-5-urea and amide derivatives
  申请人：McNeilab, Inc.

  公开号：US04803218A1

  公开（公告）日：1989-02-07

  Compounds useful as antihypertensive agents which are 3-aminoalkyl-1H-indole-5-urea or amide derivatives having the following formula: ##STR1## or a pharmaceutically acceptable acid addition salts thereof, wherein: R is C.sub.1-4 loweralkyl, C.sub.1-4 loweralkoxy, phenyl, ##STR2## pyrrolyl, pyridyl or is a substituted nitrogen represented by: ##STR3## wherein R.sub.1 is H or a C.sub.1-4 loweralkyl or phenyl or cycloalkyl; R.sub.2 is H or a C.sub.1-4 loweralkyl; Y is H or halo; R.sub.3 is H or a C.sub.1-4 loweralkyl; R.sub.4 is H or a C.sub.1-4 loweralkyl; R.sub.5 is H or a C.sub.1-4 loweralkyl or carboxymethyl or carboxytrifluoromethyl; R.sub.6 is H or a C.sub.1-4 loweralkyl, and R.sub.5 and R.sub.6 may also be taken together as an N-loweralkyl-pyrrolidinylidene group.

  以下为翻译结果： 该化合物是3-氨基烷基-1H-吲哚-5-脲或酰胺衍生物，可用作降压剂。其化学式如下：##STR1## 或其药学上可接受的酸加成盐，其中：R为C.sub.1-4低烷基，C.sub.1-4低烷氧基，苯基，##STR2## 吡咯基，吡啶基或是一个被代替的氮原子，表示为：##STR3## 其中，R.sub.1为H或C.sub.1-4低烷基、苯基或环烷基；R.sub.2为H或C.sub.1-4低烷基；Y为H或卤素；R.sub.3为H或C.sub.1-4低烷基；R.sub.4为H或C.sub.1-4低烷基；R.sub.5为H或C.sub.1-4低烷基、羧甲基或羧基三氟甲基；R.sub.6为H或C.sub.1-4低烷基，且R.sub.5和R.sub.6也可以组成一个N-低烷基-吡咯烷基亚胺基团。
• N-(2-ARYLETHYL)BENZYLAMINES AS ANTAGONISTS OF THE 5-HT6 RECEPTOR
  申请人：Chen Zhaogen

  公开号：US20070099909A1

  公开（公告）日：2007-05-03

  The present invention provides compounds of formula (I), which are antagonists of the 5-HT 6 receptor.

  本发明提供了公式（I）的化合物，它们是5-HT6受体的拮抗剂。