1-[(4-Bromophenyl)methyl]-5-(trifluoromethoxy)-1H-indole-2,3-dione | 1160247-88-0

• 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: 1-[(4-Bromophenyl)methyl]-5-(trifluoromethoxy)-1H-indole-2,3-dione
• 英文别名: 1-[(4-bromophenyl)methyl]-5-(trifluoromethoxy)indole-2,3-dione
• CAS: 1160247-88-0
• 化学式: C₁₆H₉BrF₃NO₃
• 分子量: 400.152
• InChiKey: KNDNRZHNOCUJFL-UHFFFAOYSA-N

物化性质

• 沸点：
  473.4±55.0 °C(Predicted)
• 密度：
  1.685±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(4-Bromophenyl)methyl]-5-(trifluoromethoxy)-1H-indole-2,3-dione 、 2-氯-5-吡啶硼酸 在 bis[tris( 1,1-dimethylethyl)phosphine]-palladium 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.33h， 生成 VU0365118
  参考文献：
  名称：

  Chemical lead optimization of a pan Gq mAChR M1, M3, M5 positive allosteric modulator (PAM) lead. Part I: Development of the first highly selective M5 PAM

  摘要：

  This Letter describes a chemical lead optimization campaign directed at VU0238429, the first M-5-preferring positive allosteric modulator (PAM), discovered through analog work around VU0119498, a pan G(q) mAChR M-1, M-3, M-5 PAM. An iterative library synthesis approach delivered the first selective M-5 PAM (no activity at M-1-M-4 @ 30 mu M), and an important tool compound to study the role of M-5 in the CNS. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.089
• 作为产物：
  描述：

  对溴溴苄 、 5-三氟甲氧基吲哚-2,3-二酮 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以99%的产率得到1-[(4-Bromophenyl)methyl]-5-(trifluoromethoxy)-1H-indole-2,3-dione
  参考文献：
  名称：

  Chemical lead optimization of a pan Gq mAChR M1, M3, M5 positive allosteric modulator (PAM) lead. Part I: Development of the first highly selective M5 PAM

  摘要：

  This Letter describes a chemical lead optimization campaign directed at VU0238429, the first M-5-preferring positive allosteric modulator (PAM), discovered through analog work around VU0119498, a pan G(q) mAChR M-1, M-3, M-5 PAM. An iterative library synthesis approach delivered the first selective M-5 PAM (no activity at M-1-M-4 @ 30 mu M), and an important tool compound to study the role of M-5 in the CNS. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.089

文献信息

• Heterobiaryl and heterobiaryl ether derived M5 positive allosteric modulators
  作者：Thomas M. Bridges、J. Phillip Kennedy、Corey R. Hopkins、P. Jeffrey Conn、Craig W. Lindsley

  DOI：10.1016/j.bmcl.2010.08.042

  日期：2010.10

  This Letter describes a chemical lead optimization campaign directed at VU0238429, the first M-5-preferring positive allosteric modulator (PAM), discovered through analog work around VU0119498, a pan G(q) mAChR M-1, M-3, M-5 PAM. An iterative parallel synthesis approach was employed to incorporate basic heterocycles to improve physiochemical properties. (C) 2010 Elsevier Ltd. All rights reserved.
• Chemical lead optimization of a pan Gq mAChR M1, M3, M5 positive allosteric modulator (PAM) lead. Part I: Development of the first highly selective M5 PAM
  作者：Thomas M. Bridges、J. Phillip Kennedy、Hyekyung P. Cho、Micah L. Breininger、Patrick R. Gentry、Corey R. Hopkins、P. Jeffrey Conn、Craig W. Lindsley

  DOI：10.1016/j.bmcl.2009.11.089

  日期：2010.1

  This Letter describes a chemical lead optimization campaign directed at VU0238429, the first M-5-preferring positive allosteric modulator (PAM), discovered through analog work around VU0119498, a pan G(q) mAChR M-1, M-3, M-5 PAM. An iterative library synthesis approach delivered the first selective M-5 PAM (no activity at M-1-M-4 @ 30 mu M), and an important tool compound to study the role of M-5 in the CNS. (C) 2009 Elsevier Ltd. All rights reserved.