3-allyl-1H-indole-2-carboxylic acid | 908105-30-6

• 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-allyl-1H-indole-2-carboxylic acid
• 英文别名: 3-Allyl-2-indolecarboxylic acid；3-prop-2-enyl-1H-indole-2-carboxylic acid
• CAS: 908105-30-6
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: MFWJRIIPEPIWOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-allyl-1H-indole-2-carboxylic acid 在 lithium hydroxide monohydrate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.0h， 生成 3-allyl-1-methylindole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of tetrahydro[1,4]diazepino[1,2-a]indol-1-ones as cyclin-dependent kinase inhibitors

  摘要：

  New series of 2,3,4,5-tetrahydro[1,4]diazepino[1,2-a]indol-1-ones and 3,4,5,10-tetrahydro-2H-diazepino[3,4-b]indol-1-ones have been synthesized through an iodolactonisation/lactone-to-lactam rearrangement sequence. These compounds were evaluated as potential protein kinase inhibitors (CDK1, CDK5 and GSK-3). 11-Iodo-2,3,4,5-tetrahydro[1,4]diazepino[1,2-a]indol-1-one derivatives exhibited sub-micromolar inhibitory activity against cyclin-dependent kinases. Docking studies were realized to determine the binding mode of the inhibitors into the ATP binding domain of the CDK5 catalytic site. Our result highlighted two weak Van-der-Waals bonding interactions established between the iodine atom and both phenyl group of Phe 80 and ammonium end of Lys 33.

  DOI：

  10.1016/j.ejmech.2014.06.063
• 作为产物：
  描述：

  1-tert-butyl 2-ethyl-3-iodo-1H-indole-1,2-dicarboxylate 在 四(三苯基膦)钯 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 24.0h， 生成 3-allyl-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of tetrahydro[1,4]diazepino[1,2-a]indol-1-ones as cyclin-dependent kinase inhibitors

  摘要：

  New series of 2,3,4,5-tetrahydro[1,4]diazepino[1,2-a]indol-1-ones and 3,4,5,10-tetrahydro-2H-diazepino[3,4-b]indol-1-ones have been synthesized through an iodolactonisation/lactone-to-lactam rearrangement sequence. These compounds were evaluated as potential protein kinase inhibitors (CDK1, CDK5 and GSK-3). 11-Iodo-2,3,4,5-tetrahydro[1,4]diazepino[1,2-a]indol-1-one derivatives exhibited sub-micromolar inhibitory activity against cyclin-dependent kinases. Docking studies were realized to determine the binding mode of the inhibitors into the ATP binding domain of the CDK5 catalytic site. Our result highlighted two weak Van-der-Waals bonding interactions established between the iodine atom and both phenyl group of Phe 80 and ammonium end of Lys 33.

  DOI：

  10.1016/j.ejmech.2014.06.063

文献信息

• Substituted indole-2-carboxylic acids as glucosyl transferase inhibitors
  申请人：Pfizer Products Inc.

  公开号：EP0894789A1

  公开（公告）日：1999-02-03

  5-Carbonylaryl, 5-carbonylalkyl and 5-carbonylcycloalkyl-3-alkyl-indole-2-carboxylic acids of formula (I) are useful as UGGTASE inhibitors. wherein:    R1 is hydrogen or (C1-C6)alkyl; and    R2 is (C1-C6)alkyl, (C3-C7)cycloalkyl, phenyl or phenyl substituted with one to three groups independently selected from (C1-C3)alkyl, (C1-C3)alkoxy, halogen, cyano or nitro; or    a pharmaceutically acceptable salt thereof.

  式 (I) 的 5-羰基芳基、5-羰基烷基和 5-羰基环烷基-3-烷基-吲哚-2-羧酸可用作 UGGTASE 抑制剂。 其中 R1 是氢或(C1-C6)烷基；以及 R2 是(C1-C6)烷基、(C3-C7)环烷基、苯基或被一至三个独立选自(C1-C3)烷基、(C1-C3)烷氧基、卤素、氰基或硝基的基团取代的苯基；或 其药学上可接受的盐。
• JPH11100367A
  申请人：——

  公开号：JPH11100367A

  公开（公告）日：1999-04-13
• US5981762A
  申请人：——

  公开号：US5981762A

  公开（公告）日：1999-11-09
• Synthesis and biological evaluation of tetrahydro[1,4]diazepino[1,2-a]indol-1-ones as cyclin-dependent kinase inhibitors
  作者：Aurélien Putey、Guy Fournet、Olivier Lozach、Lionel Perrin、Laurent Meijer、Benoît Joseph

  DOI：10.1016/j.ejmech.2014.06.063

  日期：2014.8

  New series of 2,3,4,5-tetrahydro[1,4]diazepino[1,2-a]indol-1-ones and 3,4,5,10-tetrahydro-2H-diazepino[3,4-b]indol-1-ones have been synthesized through an iodolactonisation/lactone-to-lactam rearrangement sequence. These compounds were evaluated as potential protein kinase inhibitors (CDK1, CDK5 and GSK-3). 11-Iodo-2,3,4,5-tetrahydro[1,4]diazepino[1,2-a]indol-1-one derivatives exhibited sub-micromolar inhibitory activity against cyclin-dependent kinases. Docking studies were realized to determine the binding mode of the inhibitors into the ATP binding domain of the CDK5 catalytic site. Our result highlighted two weak Van-der-Waals bonding interactions established between the iodine atom and both phenyl group of Phe 80 and ammonium end of Lys 33.

表征谱图