2-Cyclopropyl-3-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acid | 562868-19-3

• 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-Cyclopropyl-3-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acid
• 英文别名: 2-Cyclopropyl-3-oxoisoindoline-4-carboxylic acid；2-cyclopropyl-3-oxo-1H-isoindole-4-carboxylic acid
• CAS: 562868-19-3
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: CCDQHNCFESKQJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• 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：

  2-Cyclopropyl-3-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以34%的产率得到(2-cyclopropyl-2,3-dihydro-1H-isoindol-4-yl)methanol
  参考文献：
  名称：

  The interaction of 4-hydroxymethyl isoindolines with dehydrobenzene. Synthesis of 3-phenylaminomethyldihydrobenzo[c]furanes

  摘要：

  2-Alkyl or 2-aryl-substituted 4-hydroxymethylisoindolines smoothly undergo intramolecular recyclization through reaction with arynes to give isobenzofurans with good yields. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.01.022
• 作为产物：
  描述：

  (1S,5R,6S,7R)-3-Cyclopropyl-4-oxo-10-oxa-3-aza-tricyclo[5.2.1.0^1,5]dec-8-ene-6-carboxylic acid 在 磷酸 作用下， 反应 1.0h， 以22%的产率得到2-Cyclopropyl-3-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acid
  参考文献：
  名称：

  Preparative Synthesis of 7-Carboxy-2-R-isoindol-1-ones

  摘要：

  DOI：

  10.1023/b:cohc.0000023763.75894.63

文献信息

• Development of a Selective Inhibitor of Protein Arginine Deiminase 2
  作者：Aaron Muth、Venkataraman Subramanian、Edward Beaumont、Mitesh Nagar、Philip Kerry、Paul McEwan、Hema Srinath、Kathleen Clancy、Sangram Parelkar、Paul R. Thompson

  DOI：10.1021/acs.jmedchem.7b00274

  日期：2017.4.13

  Protein arginine deiminase 2 (PAD2) plays a key role in the onset and progression of multiple sclerosis, rheumatoid arthritis, and breast cancer. To date, no PAD2-selective inhibitor has been developed. Such a compound will be critical for elucidating the biological roles of this isozyme and may ultimately be useful for treating specific diseases in which PAD2 activity is dysregulated. To achieve this goal, we synthesized a series of benzimidazole-based derivatives of Cl-amidine, hypothesizing that this scaffold would allow access to a series of PAD2-selective inhibitors with enhanced cellular efficacy. Herein, we demonstrate that substitutions at both the N-terminus and C-terminus of Cl-amidine result in >100-fold increases in PAD2 potency and selectivity (30a, 41a, and 49a) as well as cellular efficacy (30a). Notably, these compounds use the far less reactive fluoroacetamidine warhead. In total, we predict that 30a will be a critical tool for understanding cellular PAD2 function and sets the stage for treating diseases in which PAD2 activity is dysregulated.
• Preparative Synthesis of 7-Carboxy-2-R-isoindol-1-ones
  作者：A. V. Varlamov、E. V. Boltukhina、F. I. Zubkov、N. V. Sidorenko、A. I. Chernyshev、D. G. Grudinin

  DOI：10.1023/b:cohc.0000023763.75894.63

  日期：2004.1
• The interaction of 4-hydroxymethyl isoindolines with dehydrobenzene. Synthesis of 3-phenylaminomethyldihydrobenzo[c]furanes
  作者：Alexey V. Varlamov、Natalia I. Guranova、Tatiana N. Borisova、Flavien A.A. Toze、Maxim V. Ovcharov、Sindi Kristancho、Leonid G. Voskressensky

  DOI：10.1016/j.tet.2015.01.022

  日期：2015.2

  2-Alkyl or 2-aryl-substituted 4-hydroxymethylisoindolines smoothly undergo intramolecular recyclization through reaction with arynes to give isobenzofurans with good yields. (C) 2015 Elsevier Ltd. All rights reserved.