5-phenyl-5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indole | 84504-57-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-phenyl-5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indole
• 英文别名: 1,2,3,4-tetrahydro-1,3-ethano-5-phenylpyrido [4,3-b]indole；9-phenyl-9,15-diazatetracyclo[10.2.1.02,10.03,8]pentadeca-2(10),3,5,7-tetraene
• CAS: 84504-57-4
• 化学式: C₁₉H₁₈N₂
• 分子量: 274.365
• InChiKey: MIZKDYBHLUZOTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  17
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-phenyl-5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indole 在 sodium 作用下， 以 四氢呋喃 、 ammonium hydroxide 为溶剂， 以83%的产率得到(1R,2R,10S,12S)-9-phenyl-9,15-diazatetracyclo[10.2.1.02,10.03,8]pentadeca-3,5,7-triene
  参考文献：
  名称：

  立体化学互补减少吲哚

  摘要：

  取决于还原剂的选择，含有2、3-稠合的桥环的吲哚经历高度立体选择性地还原为具有-立体化学的-稠合衍生物。

  DOI：

  10.1016/s0040-4039(00)81957-7
• 作为产物：
  描述：

  3-(Diphenyl-hydrazono)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid 2,2,2-trichloro-ethyl ester 在 盐酸 、 溶剂黄146 、 锌 作用下， 生成 5-phenyl-5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indole
  参考文献：
  名称：

  立体化学互补减少吲哚

  摘要：

  取决于还原剂的选择，含有2、3-稠合的桥环的吲哚经历高度立体选择性地还原为具有-立体化学的-稠合衍生物。

  DOI：

  10.1016/s0040-4039(00)81957-7

文献信息

• Synthesis and in vitro evaluation of 5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indoles: high-affinity ligands for the N,N'-di-o-tolylguanidine-labeled .sigma. binding site
  作者：Richard E. Mewshaw、Ronald G. Sherrill、Rose M. Mathew、Carl Kaiser、Michael A. Bailey、E. William Karbon

  DOI：10.1021/jm00055a005

  日期：1993.2

  A series of 5,6,7,8,9,10-hexahydro-7,10-iminocyclo[b]indoles substituted at the 5 and/or 11 positions was synthesized from tropinone. Affinity for sigma binding sites was determined using [H-3]-N,N'-di-o-tolylguanidine ([H-3]DTG) and [H-3]-(+)-3-(3-hydroxyphenyl)-N-1-propylpiperidine ([H-3]-(+)-3-PPP) and for the dopamine D2 receptor labeled with [H-3]sulpiride. Nearly all compounds studied in this series possessed a higher affinity for [H-3]DTG than [H-3]-(+)-PPP-labeled sigma sites, suggesting that [H-3]DTG and [H-3]-(+)-3-PPP radioligands label pharmacologically distinct sigma binding sites, as reported previously. Substitution at the 11 position with side chains containing a four-carbon tether resulted in compounds having the highest affinity for the [H-3]DTG-labeled a site. The most potent and selective member of this series was 11-[4-(2-furanyl)butyl]-5,6,7,8,9, 10-hexahydro-7,10-iminocyclohept[b]indole(40). Enantioselectivity was investigated by preparing the (+)- and (-)-isomers of 40. These studies revealed that (+)-40 was more potent at the [H-3]-DTG-labeled sigma site whereas (-)-40 had a higher affinity at sigma sites labeled with [H-3]-(+)-PPP. Racemic 40 was observed to possess a higher affinity than either of its respective enantiomers at both the [H-3]DTG- and [H-3]-(+)-3-PPP-labeled sites, suggesting an allosteric interaction.
• Bridged .gamma.-carbolines and derivatives possessing selective and combined affinity for 5-HT2 and D2 receptors
  作者：Richard E. Mewshaw、Lisa S. Silverman、Rose M. Mathew、Carl Kaiser、Ronald G. Sherrill、Menyan Cheng、Carol W. Tiffany、E. William Karbon、Michael A. Bailey

  DOI：10.1021/jm00062a023

  日期：1993.5

  A series of 5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indoles and 6,7,8,9,10,11-hexahydro-7,-11-imino-5H-cyclooct[b]indoles was prepared. Structural modifications of the lead compound, 11-[4-(4-fluorobenzoyl)propyl]-5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indole (5, K(i) = 0.82 nM vs [H-3]ketanserin) enabled the identification of the functionality necessary for high affinity at serotonin 5-HT2 and dopamine D2 receptors in ligand binding studies. The indole ring, as well as the benzoyl or isosteric benzisoxazole moiety, were essential for high affinity. Variations of the length of the side chains resulted in ligands having either selective affinity for the 5-HT2 receptor or a combination of 5-HT2 and D2 affinity. In vivo binding studies were performed on selected members in this series. The most potent member, 2-fluoro-11-[4-(4-fluorobenzoyl)butyl]-5,6,7,8,9,-10-hexahydro-7,10-iminocyclohept[b]indole (36) had an ED50 of <1 mg/kg at the 5-HT2 and D2 receptors following oral administration.
• BERGER, J. G.;TAHBAZ, P.;MCPHAIL, A. T.;ONAN, K. D., TETRAHEDRON LETT., 1983, 24, N 24, 2469-2472
  作者：BERGER, J. G.、TAHBAZ, P.、MCPHAIL, A. T.、ONAN, K. D.

  DOI：——

  日期：——
• US5250537A
  申请人：——

  公开号：US5250537A

  公开（公告）日：1993-10-05
• Stereochemically complementary reductions of indoles
  作者：Joel G. Berger、Pirouz Tahbaz、Andrew T. McPhail、Kay D. Onan

  DOI：10.1016/s0040-4039(00)81957-7

  日期：1983.1

  Indoles containing a 2, 3-fused bridged ring undergo highly stereoselective reduction to -fused derivatives with the - stereochemistry depending on choice of reducing agent.

  取决于还原剂的选择，含有2、3-稠合的桥环的吲哚经历高度立体选择性地还原为具有-立体化学的-稠合衍生物。