2,3-dihydro-4-amino-2-(tricyclo[3.3.1.1^3,7]dec-2-yl)-1H-isoindol-1-one

• 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: 2,3-dihydro-4-amino-2-(tricyclo[3.3.1.1^3,7]dec-2-yl)-1H-isoindol-1-one
• 英文别名: 2-(2-adamantyl)-4-amino-3H-isoindol-1-one
• 化学式: C₁₈H₂₂N₂O
• 分子量: 282.385
• InChiKey: BAPSHQGFMYTJJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基-3-硝基苯甲酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 甲醇 、 四氯化碳 、 N,N-二甲基乙酰胺 为溶剂， 反应 87.0h， 生成 2,3-dihydro-4-amino-2-(tricyclo[3.3.1.1^3,7]dec-2-yl)-1H-isoindol-1-one
  参考文献：
  名称：

  Design, synthesis and biological assessment of N-adamantyl, substituted adamantyl and noradamantyl phthalimidines for nitrite, TNF-α and angiogenesis inhibitory activities

  摘要：

  A library of 15 novel and heretofore uncharacterized adamantyl and noradamantyl phthalimidines was synthesized and evaluated for neuroprotective and anti-angiogenic properties. Phthalimidine treatment in LPS-challenged cells effected reductions in levels of secreted TNF-alpha and nitrite relative to basal amounts. The primary SAR suggests nitration of adamantyl phthalimidines has marginal effect on TNF-alpha activity but promotes anti-nitrite activity; thioamide congeners retain anti-nitrite activity but are less effective reducing TNF-alpha. Site-specific nitration and thioamidation provided phthalimidine 24, effecting an 88.5% drop in nitrite concurrent with only a 4% drop in TNF-alpha. Notable anti-angiogenesis activity was observed for 20, 21 and 22. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2018.01.032

文献信息

• Thalidomide analogs and methods of use
  申请人：THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：US10730835B2

  公开（公告）日：2020-08-04

  Thalidomide analogs and methods of using the thalidomide analogs are disclosed. Some embodiments of the disclosed compounds exhibit anti-angiogenic and/or anti-inflammatory activity. Certain embodiments of the disclosed compounds are non-teratogenic.

  本研究公开了沙利度胺类似物和使用沙利度胺类似物的方法。所公开化合物的某些实施方案具有抗血管生成和/或抗炎活性。所公开化合物的某些实施方案不致畸。
• THALIDOMIDE ANALOGS AND METHODS OF USE
  申请人：The USA, as represented by the Secretary, Department of Health and Human Services

  公开号：US20200325102A1

  公开（公告）日：2020-10-15

  Thalidomide analogs and methods of using the thalidomide analogs are disclosed. Some embodiments of the disclosed compounds exhibit anti-angiogenic and/or anti-inflammatory activity. Certain embodiments of the disclosed compounds are non-teratogenic.
• Design, synthesis and biological assessment of N-adamantyl, substituted adamantyl and noradamantyl phthalimidines for nitrite, TNF-α and angiogenesis inhibitory activities
  作者：Weiming Luo、David Tweedie、Shaunna L. Beedie、Neil Vargesson、William D. Figg、Nigel H. Greig、Michael T. Scerba

  DOI：10.1016/j.bmc.2018.01.032

  日期：2018.5

  A library of 15 novel and heretofore uncharacterized adamantyl and noradamantyl phthalimidines was synthesized and evaluated for neuroprotective and anti-angiogenic properties. Phthalimidine treatment in LPS-challenged cells effected reductions in levels of secreted TNF-alpha and nitrite relative to basal amounts. The primary SAR suggests nitration of adamantyl phthalimidines has marginal effect on TNF-alpha activity but promotes anti-nitrite activity; thioamide congeners retain anti-nitrite activity but are less effective reducing TNF-alpha. Site-specific nitration and thioamidation provided phthalimidine 24, effecting an 88.5% drop in nitrite concurrent with only a 4% drop in TNF-alpha. Notable anti-angiogenesis activity was observed for 20, 21 and 22. Published by Elsevier Ltd.