1-(2,6-Dichloro-benzyl)-1H-indol-7-ylamine | 688317-00-2

• 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
• 英文名称: 1-(2,6-Dichloro-benzyl)-1H-indol-7-ylamine
• 英文别名: 1-[(2,6-Dichlorophenyl)methyl]indol-7-amine；1-[(2,6-dichlorophenyl)methyl]indol-7-amine
• CAS: 688317-00-2
• 化学式: C₁₅H₁₂Cl₂N₂
• 分子量: 291.18
• InChiKey: UDTHIGSQVDOHRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  31
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2,6-Dichloro-benzyl)-1H-indol-7-ylamine 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-Amino-2-[(S)-2-{3-[1-(2,6-dichloro-benzyl)-3-pyrrolidin-1-ylmethyl-1H-indol-7-yl]-ureido}-3-(3,4-difluoro-phenyl)-propionylamino]-N-(2-pyrrolidin-1-yl-ethyl)-butyramide
  参考文献：
  名称：

  High-affinity thrombin receptor (PAR-1) ligands: a new generation of indole-based peptide mimetic antagonists with a basic amine at the C-terminus

  摘要：

  A new generation of indole-based peptide mimetics, bearing a basic amine at the C-terminus, was developed by the agency of two complementary, multistep, trityl resin-based approaches. Thus, we obtained several high-affinity thrombin receptor (PAR-1) ligands, such as 32 and 34. Compounds 32 and 34 were found to bind to PAR-1 with excellent affinity IC50 = 25 and 35 nM, respectively) and to effectively block platelet aggregation induced by SFLLRN-NH2 (TRAP-6) and alpha-thrombin. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00325-1
• 作为产物：
  描述：

  2,6-二氯苄基溴 在 三氯化铁 、 甲烷 、 caesium carbonate 、 偏二甲肼 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-(2,6-Dichloro-benzyl)-1H-indol-7-ylamine
  参考文献：
  名称：

  High-affinity thrombin receptor (PAR-1) ligands: a new generation of indole-based peptide mimetic antagonists with a basic amine at the C-terminus

  摘要：

  A new generation of indole-based peptide mimetics, bearing a basic amine at the C-terminus, was developed by the agency of two complementary, multistep, trityl resin-based approaches. Thus, we obtained several high-affinity thrombin receptor (PAR-1) ligands, such as 32 and 34. Compounds 32 and 34 were found to bind to PAR-1 with excellent affinity IC50 = 25 and 35 nM, respectively) and to effectively block platelet aggregation induced by SFLLRN-NH2 (TRAP-6) and alpha-thrombin. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00325-1

文献信息

• Discovery of Potent Succinate-Ubiquinone Oxidoreductase Inhibitors via Pharmacophore-linked Fragment Virtual Screening Approach
  作者：Li Xiong、Xiao-Lei Zhu、Hua-Wei Gao、Yu Fu、Sheng-Quan Hu、Li-Na Jiang、Wen-Chao Yang、Guang-Fu Yang

  DOI：10.1021/acs.jafc.6b00325

  日期：2016.6.22

  Succinate-ubiquinone oxidoreductase (SQR) is an attractive target for fungicide discovery. Herein, we report the discovery of novel SQR inhibitors using a pharmacophore-linked fragment virtual screening approach, a new drug design method developed in our laboratory. Among newly designed compounds, compound 9s was identified as the most potent inhibitor with a value of 34 nM against porcine SQR, displaying approximately 10-fold higher potency than that of the commercial control penthiopyrad. Further inhibitory kinetics studies revealed that compound 9s is a noncompetitive inhibitor with respect to the substrate cytochrome c and DCIP. Interestingly, compounds 8a, 9h, 9j, and 9k exhibited good in vivo preventive effects against Rhizoctonia solani. The results obtained from molecular modeling showed that the orientation of the R-2 group had a significant effect on binding with the protein.
• High-affinity thrombin receptor (PAR-1) ligands: a new generation of indole-based peptide mimetic antagonists with a basic amine at the C-terminus
  作者：Han-Cheng Zhang、Kimberly B. White、David F. McComsey、Michael F. Addo、Patricia Andrade-Gordon、Claudia K. Derian、Donna Oksenberg、Bruce E. Maryanoff

  DOI：10.1016/s0960-894x(03)00325-1

  日期：2003.7

  A new generation of indole-based peptide mimetics, bearing a basic amine at the C-terminus, was developed by the agency of two complementary, multistep, trityl resin-based approaches. Thus, we obtained several high-affinity thrombin receptor (PAR-1) ligands, such as 32 and 34. Compounds 32 and 34 were found to bind to PAR-1 with excellent affinity IC50 = 25 and 35 nM, respectively) and to effectively block platelet aggregation induced by SFLLRN-NH2 (TRAP-6) and alpha-thrombin. (C) 2003 Elsevier Science Ltd. All rights reserved.