5-oxo-1-(tert-butoxycarbonyl)-2,3,3a,4,5,6,7,7a-octahydroindole | 143268-07-9

• 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: 5-oxo-1-(tert-butoxycarbonyl)-2,3,3a,4,5,6,7,7a-octahydroindole
• 英文别名: (3AS,7AR)-Tert-butyl 5-oxooctahydro-1H-indole-1-carboxylate；tert-butyl (3aS,7aR)-5-oxo-3,3a,4,6,7,7a-hexahydro-2H-indole-1-carboxylate
• CAS: 143268-07-9
• 化学式: C₁₃H₂₁NO₃
• 分子量: 239.315
• InChiKey: FAFPNFIAMGOSNB-GXSJLCMTSA-N

物化性质

• 沸点：
  342.9±35.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-oxo-1-(tert-butoxycarbonyl)-2,3,3a,4,5,6,7,7a-octahydroindole 在 bis-triphenylphosphine-palladium(II) chloride potassium phenolate 、 potassium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.12h， 生成
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Manzamine Analogues

  摘要：

  The synthesis and biological evaluation of a series of analogues of manzamine A, representing partial structures of the pentacyclic ABCDE diamine core, is described. All new compounds were screened against Plasmodium falciparum and demonstrated attenuated antimalarial activity relative to that of manzamine A.

  DOI：

  10.1021/ol061320b
• 作为产物：
  描述：

  在 吡啶 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到5-oxo-1-(tert-butoxycarbonyl)-2,3,3a,4,5,6,7,7a-octahydroindole
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Manzamine Analogues

  摘要：

  The synthesis and biological evaluation of a series of analogues of manzamine A, representing partial structures of the pentacyclic ABCDE diamine core, is described. All new compounds were screened against Plasmodium falciparum and demonstrated attenuated antimalarial activity relative to that of manzamine A.

  DOI：

  10.1021/ol061320b

文献信息

• Azabicyclic compounds are central nervous system active agents
  申请人：Dart J. Michael

  公开号：US20060287290A1

  公开（公告）日：2006-12-21

  Compounds of formula (I) are novel CNS active agents that are useful for treating pain and for treating other disorders associated with the cholinergic system.

  式(I)的化合物是一种新型的中枢神经系统活性剂，可用于治疗疼痛以及与胆碱能系统相关的其他疾病的治疗。
• 6-Substituted decahydroisoquinoline-3-carboxylic acids as potent and selective conformationally constrained NMDA receptor antagonists
  作者：Paul L. Ornstein、Darryle D. Schoepp、M. Brian Arnold、Nancy K. Augenstein、David Lodge、John D. Millar、John Chambers、Jack Campbell、Jonathan W. Paschal

  DOI：10.1021/jm00097a012

  日期：1992.9

  We have prepared a series of 6-substituted decahydroisoquinoline-3-carboxylic acids, and structurally similar analogs, as potential N-methyl-D-aspartate receptor antagonists. There is a large body of evidence to support the use of such compounds as cerebroprotective agents in a variety of acute and chronic neurodegenerative disorders, where some component of glutamate-mediated excitotoxicity may exist. The compounds prepared were evaluated in vitro in both receptor binding assays ([H-3]CGS19755, [H-3]AMPA, and [H-3]kainic acid) and in a cortical wedge preparation (versus NMDA, AMPA, and kainic acid) to determine affinity, potency, and selectivity. The new amino acids were also evaluated in vivo for their ability to block NMDA-induced lethality in mice. We synthesized many of the possible diastereomers of the decahydroisoquinoline nucleus in order to examine the spatial and steric requirements for affinity at the NMDA receptor and activity as NMDA antagonists. From our structure-activity relationship we identified two potent and selective NMDA receptor antagonists, the phosphonate- and tetrazole-substituted amino acids 31a and 32a, respectively, that show good activity in animals following systemic administration. For example, 31a and 32a selectively displaced [H-3]CGS19755 binding with IC50s of 55 +/- 14 and 856 +/- 136 nM, respectively, and selectively antagonized responses due to NMDA in a cortical wedge preparation with IC50s of 0.15 +/- 0.01 and 1.39 +/- 0.29-mu-M, respectively. And compounds 31a and 32a blocked NMDA-induced lethality in mice with minimum effective doses of 1.25 and 2.5 mg/kg (intraperitoneal), respectively. These novel amino acids are among some of the most potent NMDA antagonists described thus far, and are excellent candidates for development as neuroprotective agents for a number of CNS disorders.
• Synthesis and Biological Evaluation of Manzamine Analogues
  作者：Jeffrey D. Winkler、Allyn T. Londregan、Justin R. Ragains、Mark T. Hamann

  DOI：10.1021/ol061320b

  日期：2006.7.1

  The synthesis and biological evaluation of a series of analogues of manzamine A, representing partial structures of the pentacyclic ABCDE diamine core, is described. All new compounds were screened against Plasmodium falciparum and demonstrated attenuated antimalarial activity relative to that of manzamine A.