trans-(+/-)-1,3,3a,4,5,9b-hexahydro-6-methoxy-3-methyl-2H-benz[e]indol-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: trans-(+/-)-1,3,3a,4,5,9b-hexahydro-6-methoxy-3-methyl-2H-benz[e]indol-2-one
• 英文别名: (3aS,9bS)-6-methoxy-3-methyl-3a,4,5,9b-tetrahydro-1H-benzo[e]indol-2-one
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: VRIGZRLERKRDNY-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-(+/-)-1,3,3a,4,5,9b-hexahydro-6-methoxy-3-methyl-2H-benz[e]indol-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  cis- and trans-2,3,3a,4,5,9b-Hexahydro-1H-benz[e]indoles: synthesis and evaluation of dopamine D2 and D3 receptor binding affinity

  摘要：

  cis- and trans-2,3,3a,4,5,9b-Hexahydro-1H-benz[e]indoles were synthesized as conformationally rigid analogues of 3-phenylpyrrolidine and evaluated for dopamine (DA) D-2S and D-3 receptor binding affinity. The tricyclic benz[e]indole nucleus was constructed by a previously reported reductive amination-cyclization procedure. Several unexpected side products were isolated and characterized using the general method. The trans-diastereoisomers exhibited greater affinities for the DA D-3 receptor than the corresponding cis-isomers. In both the cis- and trans- series the greatest affinity for DA D-3 receptors was shown by compounds substituted with N-n propyl or N-allyl groups. The cis-(+/-)-N-allyl derivative 21e demonstrated a D-2S /D-3 selectivity of 290. Resolution of cis-(+/-)-5 and trans-(+/-)-21c into individual enantiomers showed that in both series the more active isomer had 3aR absolute configuration. These novel Ligands may be useful tools for gaining additional information about the DA D-3 receptor. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80098-1
• 作为产物：
  描述：

  5-甲氧基-2-萘满酮 在 sodium cyanoborohydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 23.5h， 生成 trans-(+/-)-1,3,3a,4,5,9b-hexahydro-6-methoxy-3-methyl-2H-benz[e]indol-2-one
  参考文献：
  名称：

  The Preparation and Biological Activity of Lactam-Based, Non-Steroidal, Inhibitors of Human Type-1 Steroid 5α-Reductase.

  摘要：

  顺式和反式融合的贝克曼重排 反式融合的 3,4,4a,9,10,10a-六氢菲-1(2H)-酮肟的贝克曼重排反应 生成了三种氮杂环庚烷。体外检测 氮杂卓和 (3aSR,9bSR)-6-methoxy-3-methyl-1,3,3a,4,5,9b-hexahydro-2H-benz[e]indol-2-one, 由萘-1,6-二醇分四步制备的针对人类 1 型类固醇的 5α-还原酶，发现这种三环五元内酰胺是一种有效的 抑制剂（IC50 733 nM）。

  DOI：

  10.1071/c97130

文献信息

• The Preparation and Biological Activity of Lactam-Based, Non-Steroidal, Inhibitors of Human Type-1 Steroid 5α-Reductase.
  作者：Andrew D. Abell、Andrew J. Phillips、Sangeeta Budhia、Ann M. McNulty、Blake L. Neubauer

  DOI：10.1071/c97130

  日期：——

  A Beckmann rearrangement of cis- and trans-fused 3,4,4a,9,10,10a-hexahydrophenanthren-1(2H)-one oximes has yielded three azepines. An in vitro assay of the azepines and (3aSR,9bSR)-6-methoxy-3-methyl-1,3,3a,4,5,9b-hexahydro-2H-benz[e]indol-2-one, prepared in four steps from naphthalene-1,6-diol, against human type-1 steroid 5α-reductase, revealed the tricyclic five-membered lactam to be a potent inhibitor (IC50 733 nM).

  顺式和反式融合的贝克曼重排 反式融合的 3,4,4a,9,10,10a-六氢菲-1(2H)-酮肟的贝克曼重排反应 生成了三种氮杂环庚烷。体外检测 氮杂卓和 (3aSR,9bSR)-6-methoxy-3-methyl-1,3,3a,4,5,9b-hexahydro-2H-benz[e]indol-2-one, 由萘-1,6-二醇分四步制备的针对人类 1 型类固醇的 5α-还原酶，发现这种三环五元内酰胺是一种有效的 抑制剂（IC50 733 nM）。
• cis- and trans-2,3,3a,4,5,9b-Hexahydro-1H-benz[e]indoles: synthesis and evaluation of dopamine D2 and D3 receptor binding affinity
  作者：Xiaodong Song、A.Michael Crider、Sharon F. Cruse、Debasis Ghosh、Cheryl Klein-Stevens、Li Liang、Mark A. Scheideler、Annemarie Varming、Inger Søtofte

  DOI：10.1016/s0223-5234(99)80098-1

  日期：1999.6

  cis- and trans-2,3,3a,4,5,9b-Hexahydro-1H-benz[e]indoles were synthesized as conformationally rigid analogues of 3-phenylpyrrolidine and evaluated for dopamine (DA) D-2S and D-3 receptor binding affinity. The tricyclic benz[e]indole nucleus was constructed by a previously reported reductive amination-cyclization procedure. Several unexpected side products were isolated and characterized using the general method. The trans-diastereoisomers exhibited greater affinities for the DA D-3 receptor than the corresponding cis-isomers. In both the cis- and trans- series the greatest affinity for DA D-3 receptors was shown by compounds substituted with N-n propyl or N-allyl groups. The cis-(+/-)-N-allyl derivative 21e demonstrated a D-2S /D-3 selectivity of 290. Resolution of cis-(+/-)-5 and trans-(+/-)-21c into individual enantiomers showed that in both series the more active isomer had 3aR absolute configuration. These novel Ligands may be useful tools for gaining additional information about the DA D-3 receptor. (C) Elsevier, Paris.