(1R,8S,15R,19R)-18-oxa-2-azoniapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaene;bromide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (1R,8S,15R,19R)-18-oxa-2-azoniapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaene;bromide
• 化学式: Br*C₁₇H₁₆NO
• 分子量: 330.224
• InChiKey: ACMRVQKKYIHATP-WOLLCHHQSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.57
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,8S,15R,19R)-18-oxa-2-azoniapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaene;bromide 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 、 水 为溶剂， 生成 (6α*,11α*,11aβ*,12R*,16R*)-1,3,4,6,11,11a,12,14,15,16-decahydro-6,11<3',2'>-furano-2H-pyrido<1,2-b>isoquinoline hydrobromide
  参考文献：
  名称：

  Synthesis and Evaluation of 6,11-Ethanohexahydrobenzo[b]quinolizidines: A New Class of Noncompetitive N-Methyl-D-aspartate Antagonists

  摘要：

  The synthesis and in vitro and in vivo evaluation of 12,13-cycloalkyl-6,11-ethanobenzo[b]quinolizidines, a new class of noncompetitive N-methyl-D-aspartate (NMDA) antagonists acting at the PCP site on the NMDA receptor complex, is reported. Structure-activity relationship studies led to the identification of 10-hydroxy-(6 alpha,11 alpha,11 alpha beta,12R*,13S*)-1,15,16-decahydro-12H-6,11[1',2']-endo-cyclopenta-2H-pyrido[1,2-b]isoquinoline hydrobromide (5h) and 9-hydroxy-(6 alpha,11 alpha,11 alpha beta,12R*,13S*)-1,3,4,6,11,11a,13,14,15,16-decahydro-12H-6,11[1',2']-endo-cyclopenta-2H-pyrido[1,2-b]isoquinoline hydrobromide(5i), the most potent members of this series with K-i values of 2.3 +/- 0.2 and 2.3 +/- 0.5 nM, respectively. Molecular modeling studies revealed that this series of compounds occupies both lipophilic sites of the Andrews PCP receptor model and shares structural features which are common to other classes of known noncompetitive NMDA antagonists such as MK-801.

  DOI：

  10.1021/jm00013a025
• 作为产物：
  描述：

  2,3-二氢呋喃 、 苯并[b]喹嗪鎓溴化物 以 环丁砜 为溶剂， 反应 2.0h， 生成 (1R,8S,15R,19R)-18-oxa-2-azoniapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaene;bromide
  参考文献：
  名称：

  Synthesis and Evaluation of 6,11-Ethanohexahydrobenzo[b]quinolizidines: A New Class of Noncompetitive N-Methyl-D-aspartate Antagonists

  摘要：

  The synthesis and in vitro and in vivo evaluation of 12,13-cycloalkyl-6,11-ethanobenzo[b]quinolizidines, a new class of noncompetitive N-methyl-D-aspartate (NMDA) antagonists acting at the PCP site on the NMDA receptor complex, is reported. Structure-activity relationship studies led to the identification of 10-hydroxy-(6 alpha,11 alpha,11 alpha beta,12R*,13S*)-1,15,16-decahydro-12H-6,11[1',2']-endo-cyclopenta-2H-pyrido[1,2-b]isoquinoline hydrobromide (5h) and 9-hydroxy-(6 alpha,11 alpha,11 alpha beta,12R*,13S*)-1,3,4,6,11,11a,13,14,15,16-decahydro-12H-6,11[1',2']-endo-cyclopenta-2H-pyrido[1,2-b]isoquinoline hydrobromide(5i), the most potent members of this series with K-i values of 2.3 +/- 0.2 and 2.3 +/- 0.5 nM, respectively. Molecular modeling studies revealed that this series of compounds occupies both lipophilic sites of the Andrews PCP receptor model and shares structural features which are common to other classes of known noncompetitive NMDA antagonists such as MK-801.

  DOI：

  10.1021/jm00013a025

文献信息

• Synthesis and Evaluation of 6,11-Ethanohexahydrobenzo[b]quinolizidines: A New Class of Noncompetitive N-Methyl-D-aspartate Antagonists
  作者：Chakrapani Subramanyam、John P. Mallamo、Gary M. Pilling、William G. Earley、Philip M. Carabateas、Joseph R. Wetzel、Diane DeHaven-Hudkins、Timothy Allen、Rudolph K. Kullnig

  DOI：10.1021/jm00013a025

  日期：1995.6

  The synthesis and in vitro and in vivo evaluation of 12,13-cycloalkyl-6,11-ethanobenzo[b]quinolizidines, a new class of noncompetitive N-methyl-D-aspartate (NMDA) antagonists acting at the PCP site on the NMDA receptor complex, is reported. Structure-activity relationship studies led to the identification of 10-hydroxy-(6 alpha,11 alpha,11 alpha beta,12R*,13S*)-1,15,16-decahydro-12H-6,11[1',2']-endo-cyclopenta-2H-pyrido[1,2-b]isoquinoline hydrobromide (5h) and 9-hydroxy-(6 alpha,11 alpha,11 alpha beta,12R*,13S*)-1,3,4,6,11,11a,13,14,15,16-decahydro-12H-6,11[1',2']-endo-cyclopenta-2H-pyrido[1,2-b]isoquinoline hydrobromide(5i), the most potent members of this series with K-i values of 2.3 +/- 0.2 and 2.3 +/- 0.5 nM, respectively. Molecular modeling studies revealed that this series of compounds occupies both lipophilic sites of the Andrews PCP receptor model and shares structural features which are common to other classes of known noncompetitive NMDA antagonists such as MK-801.