methyl N-[2-(1-benzyl-5-methoxy-2-oxo-3H-indol-3-yl)ethyl]carbamate | 193604-38-5

• 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: methyl N-[2-(1-benzyl-5-methoxy-2-oxo-3H-indol-3-yl)ethyl]carbamate
• CAS: 193604-38-5
• 化学式: C₂₀H₂₂N₂O₄
• 分子量: 354.406
• InChiKey: LUNYEYJABIYREU-UHFFFAOYSA-N

物化性质

• 沸点：
  597.2±50.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl N-[2-(1-benzyl-5-methoxy-2-oxo-3H-indol-3-yl)ethyl]carbamate 在 palladium dihydroxide sodium hydroxide 、 氢气 、 sodium 、 三溴化硼 、 苄基三甲基溴化铵 、 红铝 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 氯仿 、 苯 为溶剂， 反应 12.67h， 生成 (-)-norphysostigmine
  参考文献：
  名称：

  Total Syntheses and Anticholinesterase Activities of (3aS)-N(8)-Norphysostigmine, (3aS)-N(8)-Norphenserine, Their Antipodal Isomers, and Other N(8)-Substituted Analogues

  摘要：

  N(8)-Benzylesermethole (6) was prepared from 5-methoxytryptamine (1) in five steps. Resolution of compound 6 by dibenzoyl- and ditoluyltartaric acid provided enantiomers (-)- and (+)-7. After demethylation, reaction with isocyanates and catalytic debenzylation over hydrogen, the total syntheses of(-)-and (+)-N(8)-norphysostigmine [(-)-and (+)-11] and (-)-and (+)N(8)-norphenserine [(-)-and (+)-12] were accomplished. (-)-N(8)-Norphysostigmine [(-)-11] and (-)-N(8)-norphenserine [(-)-12] were also obtained by transformations of natural physostigmine [(-)-13] and phenserine [(-)-14] prepared from(-)-13. The absolute configurations and optical purity of compounds (-)-11, (-)-12, (+)-11, and (+)-12 were confirmed by a comparison of their optical rotations with those of the compounds synthesized from physostigmine [(-)-13]. The anticholinesterase activities of N(8)-nor-and N(8)-substituted analogues, (-)-and (+)-9, -10, -11, -12, 15, and 16, were compared with those of physostigmine [(-)-and (+)-13] and phenserine [(-)- and (+)-14] and are reported.

  DOI：

  10.1021/jm970210v
• 作为产物：
  描述：

  5-甲氧基色胺 在 盐酸 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.66h， 生成 methyl N-[2-(1-benzyl-5-methoxy-2-oxo-3H-indol-3-yl)ethyl]carbamate
  参考文献：
  名称：

  Total Syntheses and Anticholinesterase Activities of (3aS)-N(8)-Norphysostigmine, (3aS)-N(8)-Norphenserine, Their Antipodal Isomers, and Other N(8)-Substituted Analogues

  摘要：

  N(8)-Benzylesermethole (6) was prepared from 5-methoxytryptamine (1) in five steps. Resolution of compound 6 by dibenzoyl- and ditoluyltartaric acid provided enantiomers (-)- and (+)-7. After demethylation, reaction with isocyanates and catalytic debenzylation over hydrogen, the total syntheses of(-)-and (+)-N(8)-norphysostigmine [(-)-and (+)-11] and (-)-and (+)N(8)-norphenserine [(-)-and (+)-12] were accomplished. (-)-N(8)-Norphysostigmine [(-)-11] and (-)-N(8)-norphenserine [(-)-12] were also obtained by transformations of natural physostigmine [(-)-13] and phenserine [(-)-14] prepared from(-)-13. The absolute configurations and optical purity of compounds (-)-11, (-)-12, (+)-11, and (+)-12 were confirmed by a comparison of their optical rotations with those of the compounds synthesized from physostigmine [(-)-13]. The anticholinesterase activities of N(8)-nor-and N(8)-substituted analogues, (-)-and (+)-9, -10, -11, -12, 15, and 16, were compared with those of physostigmine [(-)-and (+)-13] and phenserine [(-)- and (+)-14] and are reported.

  DOI：

  10.1021/jm970210v

文献信息

• J. Med. Chem. 1997, 40, 2895-2901
  作者：

  DOI：——

  日期：——
• J. Med. Chem. 1998, 41, 2371-2379
  作者：

  DOI：——

  日期：——
• J. Med. Chem. 1999, 42, 1855-1861
  作者：

  DOI：——

  日期：——
• Agents Useful for Reducing Amyloid Precursor Protein and Treating Dementia and Methods of Use Thereof
  申请人：Greig Nigel H.

  公开号：US20090131501A1

  公开（公告）日：2009-05-21

  The present invention provides compounds and methods of administering compounds to a subject that can reduce βAPP production and that is not toxic in a wide range of dosages. The present invention also provides non-carbamate compounds and methods of administering such compounds to a subject that can reduce βAPP production and that is not toxic in a wide range of dosages. It has been discovered that either the racemic or enantiomerically pure non-carbamate compounds can be used to decrease βAPP production.
• US7786162B2
  申请人：——

  公开号：US7786162B2

  公开（公告）日：2010-08-31