1,2,3,5-tetrahydropyrrolo<2,3-f>indole | 40995-77-5

• 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: 1,2,3,5-tetrahydropyrrolo<2,3-f>indole
• 英文别名: 1,2,3,5-tetrahydro-pyrrolo[2,3-f]indole；1,2,3,5-Tetrahydro-pyrrolo[2,3-f]indole；1,5,6,7-tetrahydropyrrolo[2,3-f]indole
• CAS: 40995-77-5
• 化学式: C₁₀H₁₀N₂
• 分子量: 158.203
• InChiKey: OYMRVJNKFVSSSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2,3,5-tetrahydropyrrolo<2,3-f>indole 在 sodium hydride 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 22.25h， 生成 5-Isopropyl-3,5-dihydro-2H-pyrrolo[2,3-f]indole-1-carboxylic acid pyridin-3-ylamide
  参考文献：
  名称：

  Synthesis, Biological Activity, and Molecular Modeling Studies of Selective 5-HT_2C/2B Receptor Antagonists

  摘要：

  The synthesis and biological activity are reported for a series of analogues of the previously published indole urea 2 (SB-206553), designed to probe the 5-HT2C receptor binding site. Small molecule modeling studies have been used to define a region in space which is allowed at the 5-HT2C receptor but disallowed at the 5-HT2A receptor. In a complementary approach, docking of 2 into our model of the 5-HT2C receptor has allowed us to propose a novel primary binding interaction for this series of diaryl ureas, involving a potential double hydrogen-bonding interaction between the urea carbonyl oxygen of the ligand and two serine residues in the receptor. The difference of two valine residues in the 5-HT2C receptor for leucine residues in the 5-HT2A receptor is believed to account for the observed 5-HT2C/5-HT2A selectivity with 2.

  DOI：

  10.1021/jm960571v
• 作为产物：
  描述：

  1-acetyl-1,2,3,5-tetrahydropyrrolo<2,3-f>indole 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以89%的产率得到1,2,3,5-tetrahydropyrrolo<2,3-f>indole
  参考文献：
  名称：

  Synthesis, Biological Activity, and Molecular Modeling Studies of Selective 5-HT_2C/2B Receptor Antagonists

  摘要：

  The synthesis and biological activity are reported for a series of analogues of the previously published indole urea 2 (SB-206553), designed to probe the 5-HT2C receptor binding site. Small molecule modeling studies have been used to define a region in space which is allowed at the 5-HT2C receptor but disallowed at the 5-HT2A receptor. In a complementary approach, docking of 2 into our model of the 5-HT2C receptor has allowed us to propose a novel primary binding interaction for this series of diaryl ureas, involving a potential double hydrogen-bonding interaction between the urea carbonyl oxygen of the ligand and two serine residues in the receptor. The difference of two valine residues in the 5-HT2C receptor for leucine residues in the 5-HT2A receptor is believed to account for the observed 5-HT2C/5-HT2A selectivity with 2.

  DOI：

  10.1021/jm960571v

文献信息

• 4-heterocyclyl-substituted quinazoline derivatives, processes for their
  申请人：Pfizer Inc.

  公开号：US05736534A1

  公开（公告）日：1998-04-07

  This invention relates to certain 4-aminoquinazolines and the pharmaceutically acceptable salts and stereoisomers thereof, the formula whereof are described herein. The compounds are useful for the treatment of hyperproliferative diseases, particularly as anti-cancer agents.

  这项发明涉及某些4-氨基喹唑啉及其药用可接受的盐和立体异构体，其公式在本文件中有所描述。这些化合物用于治疗过度增殖性疾病，特别是作为抗癌剂。
• 4-HETEROCYCLYL-SUBSTITUTED QUINAZOLINE DERIVATIVES, PROCESSES FOR THEIR PREPARATION AND THEIR USE AS ANTI-CANCER AGENTS
  申请人：PFIZER INC.

  公开号：EP0746554A1

  公开（公告）日：1996-12-11
• HETEROCYCLIC RING-FUSED PYRIMIDINE DERIVATIVES
  申请人：PFIZER INC.

  公开号：EP0831829B1

  公开（公告）日：2003-08-20
• SULPHONAMIDE DERIVATIVES BEING 5-HT6 RECEPTOR ANTAGONISTS AND PROCESS FOR THEIR PREPARATION
  申请人：SmithKline Beecham plc

  公开号：EP0994862B1

  公开（公告）日：2005-06-01
• US5736534A
  申请人：——

  公开号：US5736534A

  公开（公告）日：1998-04-07