3-[4-(4-aminopiperidin-1-yl)butyl]-1H-indole-5-carbonitrile | 1227753-14-1

• 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
• 英文名称: 3-[4-(4-aminopiperidin-1-yl)butyl]-1H-indole-5-carbonitrile
• CAS: 1227753-14-1
• 化学式: C₁₈H₂₄N₄
• 分子量: 296.415
• InChiKey: SCCGNCANKHFPCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氰基-1H-吲哚-7-羧酸 、 3-[4-(4-aminopiperidin-1-yl)butyl]-1H-indole-5-carbonitrile 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 3-cyano-1H-indole-7-carboxylic acid {1-[4-(5-cyano-1H-indol-3-yl)butyl]piperidin-4-yl}amide
  参考文献：
  名称：

  Allosteric IGF-1R Inhibitors

  摘要：

  Targeting allosteric protein sites is a promising approach to interfere selectively with cellular signaling cascades. We have discovered a novel class of allosteric insulin-like growth factor-1 receptor (IGF-1R) inhibitors. 3-Cyano-1H-indole-7-carboxylic acid {1-[4-(5-cyano-1H-indol-3-yl)butyl]piperidin-4-yl}amide (10) was found with nanomolar biochemical, micromolar, cellular IGF-1R activity and no relevant interference with cellular insulin receptor signaling up to 30 mu M. The allosteric binding site was characterized by X-ray crystallographic studies, and the structural information was used to explain the unique mode of action of this new class of inhibitors.

  DOI：

  10.1021/ml100044h
• 作为产物：
  描述：

  tert-butyl N-[1-[4-(5-cyano-1H-indol-3-yl)butyl]piperidin-4-yl]carbamate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 3-[4-(4-aminopiperidin-1-yl)butyl]-1H-indole-5-carbonitrile
  参考文献：
  名称：

  Allosteric IGF-1R Inhibitors

  摘要：

  Targeting allosteric protein sites is a promising approach to interfere selectively with cellular signaling cascades. We have discovered a novel class of allosteric insulin-like growth factor-1 receptor (IGF-1R) inhibitors. 3-Cyano-1H-indole-7-carboxylic acid {1-[4-(5-cyano-1H-indol-3-yl)butyl]piperidin-4-yl}amide (10) was found with nanomolar biochemical, micromolar, cellular IGF-1R activity and no relevant interference with cellular insulin receptor signaling up to 30 mu M. The allosteric binding site was characterized by X-ray crystallographic studies, and the structural information was used to explain the unique mode of action of this new class of inhibitors.

  DOI：

  10.1021/ml100044h

文献信息

• PROCESSES FOR THE PREPARATION OF 3-ALKYL INDOLES
  申请人：APOTEX PHARMACHEM INC.

  公开号：US20150252000A1

  公开（公告）日：2015-09-10

  This invention provides processes for preparation of 3-alkyl indoles of Formula 1: wherein A 1 , A 2 and A 3 are independently selected from the group consisting of: H, X, OR 1 , CN, CONR 2 2 and C0 2 R 3 ; R 1 is C 1 -C 6 alkyl; R 2 is H or C 1 -C 6 alkyl; R 3 is C 1 -C 6 alkyl; LG is a leaving group; X is a halogen; and n is 1, 2 or 3.

  本发明提供了制备式1中的3-烷基吲哚的方法：其中A1、A2和A3独立地选自以下组中的一种：H、X、OR1、CN、CONR22和C02R3；R1是C1-C6烷基；R2是H或C1-C6烷基；R3是C1-C6烷基；LG是离去基；X是卤素；n为1、2或3。
• US9533949B2
  申请人：——

  公开号：US9533949B2

  公开（公告）日：2017-01-03