2-(4-Methyl-2,3-dihydroindol-1-yl)ethanamine | 552866-93-0

• 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: 2-(4-Methyl-2,3-dihydroindol-1-yl)ethanamine
• CAS: 552866-93-0
• 化学式: C₁₁H₁₆N₂
• 分子量: 176.261
• InChiKey: NYDXQXMAIOPKGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-Methyl-2,3-dihydroindol-1-yl)ethanamine 、 异氰酸2-溴苯酯 以 二氯甲烷 为溶剂， 生成 1-(2-bromophenyl)-3-[2-(4-methyl-2,3-dihydro-1H-indol-1-yl)ethyl]urea
  参考文献：
  名称：

  Discovery of SB-705498: A potent, selective and orally bioavailable TRPV1 antagonist suitable for clinical development

  摘要：

  Small molecule antagonists of the vanilloid receptor TRPV1 (also known as VR1) are disclosed. Pyrrolidinyl ureas such as 8 and 15 (SB-705498) emerged as lead compounds following optimisation of the previously described urea SB-452533. Pharmacological studies using electrophysiological and FLIPR-Ca2+-based assays showed that compounds such as 8 and 15 were potent antagonists versus the multiple chemical and physical modes of TRPV1 activation (namely capsaicin, acid and noxious heat). Furthermore, 15 possessed suitable developability properties to enable progression of this compound into in vivo studies and subsequently clinical development. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.030
• 作为产物：
  描述：

  4-甲基吲哚 在 sodium cyanoborohydride 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 36.0h， 生成 2-(4-Methyl-2,3-dihydroindol-1-yl)ethanamine
  参考文献：
  名称：

  Discovery of SB-705498: A potent, selective and orally bioavailable TRPV1 antagonist suitable for clinical development

  摘要：

  Small molecule antagonists of the vanilloid receptor TRPV1 (also known as VR1) are disclosed. Pyrrolidinyl ureas such as 8 and 15 (SB-705498) emerged as lead compounds following optimisation of the previously described urea SB-452533. Pharmacological studies using electrophysiological and FLIPR-Ca2+-based assays showed that compounds such as 8 and 15 were potent antagonists versus the multiple chemical and physical modes of TRPV1 activation (namely capsaicin, acid and noxious heat). Furthermore, 15 possessed suitable developability properties to enable progression of this compound into in vivo studies and subsequently clinical development. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.030

文献信息

• Novel compounds
  申请人：Rami Kantilal Harshad

  公开号：US20060100202A1

  公开（公告）日：2006-05-11

  Compounds of formula (I) or a pharmaceutically acceptable salt or solvate thereof: wherein, R 1 , R 2 , P, p and n are as defined in the specification, a process for preparing such compounds, a pharmaceutical composition containing such compounds and the use of such compounds in medicine.

  式(I)的化合物或其药学上可接受的盐或溶剂，其中，R1，R2，P，p和n如规范中所定义，制备这种化合物的过程，包含这种化合物的药物组成物，以及这种化合物在医学上的用途。
• UREA DERIVATIVES AND THEIR USE AS VANILLOID RECEPTOR ANTAGONISTS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1474403A2

  公开（公告）日：2004-11-10
• [EN] NOVEL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO2003053945A2

  公开（公告）日：2003-07-03

  Compounds of formula (I) or a pharmaceutically acceptable salt or solvate thereof: (I) wherein, R1, R2, P, p and n are as defined in the specification, a process for preparing such compounds, a pharmaceutical composition containing such compounds and the use of such compounds in medicine.
• Discovery of SB-705498: A potent, selective and orally bioavailable TRPV1 antagonist suitable for clinical development
  作者：Harshad K. Rami、Mervyn Thompson、Geoffrey Stemp、Steve Fell、Jeffrey C. Jerman、Alexander J. Stevens、Darren Smart、Becky Sargent、Dominic Sanderson、Andrew D. Randall、Martin J. Gunthorpe、John B. Davis

  DOI：10.1016/j.bmcl.2006.03.030

  日期：2006.6

  Small molecule antagonists of the vanilloid receptor TRPV1 (also known as VR1) are disclosed. Pyrrolidinyl ureas such as 8 and 15 (SB-705498) emerged as lead compounds following optimisation of the previously described urea SB-452533. Pharmacological studies using electrophysiological and FLIPR-Ca2+-based assays showed that compounds such as 8 and 15 were potent antagonists versus the multiple chemical and physical modes of TRPV1 activation (namely capsaicin, acid and noxious heat). Furthermore, 15 possessed suitable developability properties to enable progression of this compound into in vivo studies and subsequently clinical development. (c) 2006 Elsevier Ltd. All rights reserved.