(1R)-2-[(1R)-2-methyl-2,3-dihydro-1H-isoindol-1-yl]-1-(4-methylphenyl)ethanol | 1338320-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (1R)-2-[(1R)-2-methyl-2,3-dihydro-1H-isoindol-1-yl]-1-(4-methylphenyl)ethanol
• 英文别名: (1R)-2-[(1R)-2-methyl-1,3-dihydroisoindol-1-yl]-1-(4-methylphenyl)ethanol
• CAS: 1338320-09-4
• 化学式: C₁₈H₂₁NO
• 分子量: 267.371
• InChiKey: MMJRHSLJFLGUJR-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R)-2-[(1R)-2-methyl-2,3-dihydro-1H-isoindol-1-yl]-1-(4-methylphenyl)ethanol 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 (1R)-2-[(1R)-2-methyl-1,3-dihydroisoindol-1-yl]-1-(4-methylphenyl)ethanol;hydrochloride
  参考文献：
  名称：

  Synthesis of a series of γ-amino alcohols comprising an N-methyl isoindoline moiety and their evaluation as NMDA receptor antagonists

  摘要：

  We report a series of new stereoisomeric gamma-amino alcohols comprising an N-methyl isoindoline moiety as ligands for the ifenprodil binding site of the NMDA receptor. Among the four series of stereoisomers, 8a-c, 9a-c, 10a-c, and 11a-c, synthesised, the highest potencies and NMDA-NR2B subtype selectivity was found for the methyl derivative 11a and the chloro derivative 11c, both possessing the [1S,1'S] configuration. However, additional moderate potency of 11a and 11c at the hERG channel with values of 2.6 +/- 2.4% and 1.6 +/- 2.0%, respectively, rendered them unsuitable for medical use. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.119
• 作为产物：
  描述：

  (3R,4aR)-3-(4-methylphenyl)-3,4,4a,9-tetrahydro-1,3-oxazino[4,3-a]isoindole 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以37%的产率得到(1R)-2-[(1R)-2-methyl-2,3-dihydro-1H-isoindol-1-yl]-1-(4-methylphenyl)ethanol
  参考文献：
  名称：

  Synthesis of a series of γ-amino alcohols comprising an N-methyl isoindoline moiety and their evaluation as NMDA receptor antagonists

  摘要：

  We report a series of new stereoisomeric gamma-amino alcohols comprising an N-methyl isoindoline moiety as ligands for the ifenprodil binding site of the NMDA receptor. Among the four series of stereoisomers, 8a-c, 9a-c, 10a-c, and 11a-c, synthesised, the highest potencies and NMDA-NR2B subtype selectivity was found for the methyl derivative 11a and the chloro derivative 11c, both possessing the [1S,1'S] configuration. However, additional moderate potency of 11a and 11c at the hERG channel with values of 2.6 +/- 2.4% and 1.6 +/- 2.0%, respectively, rendered them unsuitable for medical use. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.119

文献信息

• Synthesis of a series of γ-amino alcohols comprising an N-methyl isoindoline moiety and their evaluation as NMDA receptor antagonists
  作者：Andreas Müller、Georg Höfner、Thejavathi Renukappa-Gutke、Chris G. Parsons、Klaus T. Wanner

  DOI：10.1016/j.bmcl.2011.07.119

  日期：2011.10

  We report a series of new stereoisomeric gamma-amino alcohols comprising an N-methyl isoindoline moiety as ligands for the ifenprodil binding site of the NMDA receptor. Among the four series of stereoisomers, 8a-c, 9a-c, 10a-c, and 11a-c, synthesised, the highest potencies and NMDA-NR2B subtype selectivity was found for the methyl derivative 11a and the chloro derivative 11c, both possessing the [1S,1'S] configuration. However, additional moderate potency of 11a and 11c at the hERG channel with values of 2.6 +/- 2.4% and 1.6 +/- 2.0%, respectively, rendered them unsuitable for medical use. (C) 2011 Elsevier Ltd. All rights reserved.