(1'R)-N-(2'-ethyl-1'-hydroxyethyl)-1H-isoindole-1,3(2H)-dione | 169331-29-7

• 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: (1'R)-N-(2'-ethyl-1'-hydroxyethyl)-1H-isoindole-1,3(2H)-dione
• 英文别名: (R)-2-(1-hydroxybutan-2-yl)isoindoline-1,3-dione；(R)-2-(1-hydroxybut-2-yl)phthalimide；2-[(2R)-1-hydroxybutan-2-yl]isoindole-1,3-dione
• CAS: 169331-29-7
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: IBGZCJUHWHWXSL-MRVPVSSYSA-N

物化性质

• 沸点：
  368.5±25.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1'R)-N-(2'-ethyl-1'-hydroxyethyl)-1H-isoindole-1,3(2H)-dione 在 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3R,9bS)-3-Ethyl-9b-(4-fluoro-phenyl)-2,3-dihydro-9bH-oxazolo[2,3-a]isoindol-5-one
  参考文献：
  名称：

  Naira, Dinesh S.; Pauranik, Vedavati; Shaha, Amrish C., Journal of Chemical Research - Part S, 2003, # 12, p. 772 - 774

  摘要：

  DOI：
• 作为产物：
  描述：

  苯酐 、 2-氨基丁醇 反应 3.0h， 以95%的产率得到(1'R)-N-(2'-ethyl-1'-hydroxyethyl)-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  通过O-阳离子环化非对映选择性地获得手性非外消旋[1,3]恶唑-[2,3- a ] isoindol -5-one环系统†

  摘要：

  献给让·莫雷尔教授退休

  DOI：

  10.1002/jhet.5570390223

文献信息

• [EN] ARYL ETHER-BASE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASES DE TYPE ARYLÉTHER-BASE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2015038112A1

  公开（公告）日：2015-03-19

  The present disclosure is generally directed to compounds which can inhibit AAK1 (adaptor associated kinase 1), compositions comprising such compounds, and methods for inhibiting AAK1.

  本公开涉及一般可抑制AAK1（适配器相关激酶1）的化合物，包括这些化合物的组合物，以及抑制AAK1的方法。
• Aryl Ether-Base Kinase Inhibitors
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20130237555A1

  公开（公告）日：2013-09-12

  The present disclosure is generally directed to compounds which can inhibit AAK1 (adaptor associated kinase 1), compositions comprising such compounds, and methods for inhibiting AAK1.

  本公开涉及一般可抑制AAK1（适配器相关激酶1）的化合物，包括这些化合物的组合物，以及抑制AAK1的方法。
• Formation of a novel ring system: An unexpected intermolecular cyclization
  作者：G.Biju Kumar、Amrish C. Shah、Tullio Pilati

  DOI：10.1016/s0040-4039(97)00590-x

  日期：1997.5

  A novel chiral ten membered heterocyclic ring is synthesised in two steps from phthalimide derivatives of . The structures have been unambiguously established by single crystal X-ray diffraction of one of the compounds.

  新型的手性十元杂环是由邻苯二甲酰亚胺的邻苯二甲酰亚胺衍生物分两步合成的。通过化合物之一的单晶X射线衍射已明确地确定了结构。
• ARYL ETHER-BASE KINASE INHIBITORS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20160222021A1

  公开（公告）日：2016-08-04

  The present disclosure is generally directed to compounds which can inhibit AAK1 (adaptor associated kinase 1), compositions comprising such compounds, and methods for inhibiting AAK1.

  本公开涉及能够抑制AAK1（适配器相关激酶1）的化合物、包含这些化合物的组合物以及抑制AAK1的方法。
• Synthesis and in vitro antimycobacterial activity of compounds derived from (R)- and (S)-2-amino-1-butanol – The crucial role of the configuration
  作者：Georgi M. Dobrikov、Violeta Valcheva、Margarita Stoilova-Disheva、Georgi Momekov、Pavleta Tzvetkova、Angel Chimov、Vladimir Dimitrov

  DOI：10.1016/j.ejmech.2011.11.035

  日期：2012.2

  The synthesis of 47 structurally diverse compounds incorporating the (R)-2-amino-1-butanol motif has been realized. Ten of these compounds were found to exhibit in vitro specific activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.65 mu M-14.03 mu M. Five of the most active compounds 11, 22, 23, 31 and 42(5.7-11.1 fold more active than ethambutol) can be outlined with very low cytotoxicity towards human embryonal kidney non-tumour cells (SI ranging from 91.2 to 375.4). For the purpose of comparison the (S)-enantiomers of these most active compounds have been synthesized and evaluated towards M. tuberculosis H(37)Rv showing no activity even at 20-32 fold higher concentrations. (C) 2011 Elsevier Masson SAS. All rights reserved.