3-(6-nitro-1-oxo-1,3-dihydroisoindol-2-yl)butyric acid | 1335100-70-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(6-nitro-1-oxo-1,3-dihydroisoindol-2-yl)butyric acid
• 英文别名: 3-(5-nitro-3-oxo-1H-isoindol-2-yl)butanoic acid
• CAS: 1335100-70-3
• 化学式: C₁₂H₁₂N₂O₅
• 分子量: 264.238
• InChiKey: VTVQESGXTOHFJE-UHFFFAOYSA-N

物化性质

• 熔点：
  194-195 °C
• 沸点：
  524.8±50.0 °C(predicted)
• 密度：
  1.458±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 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：
  103
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(6-nitro-1-oxo-1,3-dihydroisoindol-2-yl)butyric acid 在 硫酸 、 palladium on activated charcoal 、 氢气 、 三乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 3-{6-[(2-boc-1,2,3,4-tetrahydroisoquinoline-7-carbonyl)amino]-1-oxo-1,3-dihydroisoindol-2-yl}butyric acid methyl ester
  参考文献：
  名称：

  RGD mimetics containing phthalimidine fragment as novel ligands of fibrinogen receptor

  摘要：

  The novel RGD mimetics with phthalimidine central fragment were synthesized with the use of 4-piperidine-4-yl-butyric, 4-piperidine-4-yl-butyric, 4-piperazine-4-yl-benzoic and 1,2,3,4-tetrahydroiso-quinoline-7-carboxylic acids as surrogates of Arg motif. The synthesized compounds potently inhibited platelet aggregation in vitro and blocked FITC-Fg binding to alpha(IIb)beta(3) integrin in a suspension of washed human platelets. The key alpha(IIb)beta(3) protein-ligand interactions were determined in docking experiments. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.063
• 作为产物：
  描述：

  3-(1-oxo-1,3-dihydroisoindol-2-yl)butyric acid 在 硫酸 、 硝酸 作用下， 反应 6.0h， 生成 3-(6-nitro-1-oxo-1,3-dihydroisoindol-2-yl)butyric acid
  参考文献：
  名称：

  RGD mimetics containing phthalimidine fragment as novel ligands of fibrinogen receptor

  摘要：

  The novel RGD mimetics with phthalimidine central fragment were synthesized with the use of 4-piperidine-4-yl-butyric, 4-piperidine-4-yl-butyric, 4-piperazine-4-yl-benzoic and 1,2,3,4-tetrahydroiso-quinoline-7-carboxylic acids as surrogates of Arg motif. The synthesized compounds potently inhibited platelet aggregation in vitro and blocked FITC-Fg binding to alpha(IIb)beta(3) integrin in a suspension of washed human platelets. The key alpha(IIb)beta(3) protein-ligand interactions were determined in docking experiments. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.063

文献信息

• Synthesis, biological evaluation, X-ray molecular structure and molecular docking studies of RGD mimetics containing 6-amino-2,3-dihydroisoindolin-1-one fragment as ligands of integrin αIIbβ3
  作者：Andrei A. Krysko、Georgiy V. Samoylenko、Pavel G. Polishchuk、Marina S. Fonari、Victor Ch. Kravtsov、Sergei A. Andronati、Tatyana A. Kabanova、Janusz Lipkowski、Tetiana M. Khristova、Victor E. Kuz’min、Vladimir M. Kabanov、Olga L. Krysko、Alexandre A. Varnek

  DOI：10.1016/j.bmc.2013.05.019

  日期：2013.8

  A series of novel RGD mimetics containing phthalimidine fragment was designed and synthesized. Their antiaggregative activity determined by Born's method was shown to be due to inhibition of fibrinogen binding to alpha(IIb)beta(3). Molecular docking of RGD mimetics to alpha(IIb)beta(3) receptor showed the key interactions in this complex, and also some correlations have been observed between values of biological activity and docking scores. The single crystal X-ray data were obtained for five mimetics. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.