2-(4-硝基-苯基)-1,3-二氧代-2,3-二氢-1H-异5-吲哚甲酸 | 110768-20-2

• 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
• 中文名称: 2-(4-硝基-苯基)-1,3-二氧代-2,3-二氢-1H-异5-吲哚甲酸
• 英文名称: 2-(4-nitrophenyl)-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
• 英文别名: 2-(4-nitrophenyl)isoindoline-1,3-dione-5-benzoic acid；2-(4-Nitrophenyl)-1,3-dioxoisoindoline-5-carboxylic acid；2-(4-nitrophenyl)-1,3-dioxoisoindole-5-carboxylic acid
• CAS: 110768-20-2
• 化学式: C₁₅H₈N₂O₆
• mdl: MFCD00187716
• 分子量: 312.238
• InChiKey: ZQQMHXVUPKKVJQ-UHFFFAOYSA-N

物化性质

• 熔点：
  287-288 °C
• 沸点：
  627.3±65.0 °C(Predicted)
• 密度：
  1.633±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-(4-硝基-苯基)-1,3-二氧代-2,3-二氢-1H-异5-吲哚甲酸 在 manganese(IV) oxide 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 12.25h， 生成 (2-(4-nitrophenyl)isoindoline-5-carbaldheyde)
  参考文献：
  名称：

  Synthesis and investigation of donor–porphyrin–acceptor triads with long-lived photo-induced charge-separate states

  摘要：

  强电子给体四烷基苯二胺（TAPD）促进了光诱导电子转移，即使在10K的冻结溶剂中也能产生长寿命的自旋极化电荷分离态，可以通过EPR观察到。

  DOI：

  10.1039/c5sc01830g
• 作为产物：
  描述：

  4-硝基苯胺 、 偏苯三酸酐 以 溶剂黄146 为溶剂， 反应 20.0h， 以95%的产率得到2-(4-硝基-苯基)-1,3-二氧代-2,3-二氢-1H-异5-吲哚甲酸
  参考文献：
  名称：

  Synthesis and investigation of donor–porphyrin–acceptor triads with long-lived photo-induced charge-separate states

  摘要：

  强电子给体四烷基苯二胺（TAPD）促进了光诱导电子转移，即使在10K的冻结溶剂中也能产生长寿命的自旋极化电荷分离态，可以通过EPR观察到。

  DOI：

  10.1039/c5sc01830g

文献信息

• Design, Synthesis, and Structure−Activity Relationships of Phthalimide-Phenylpiperazines:  A Novel Series of Potent and Selective α₁_a-Adrenergic Receptor Antagonists
  作者：Gee-Hong Kuo、Catherine Prouty、William V. Murray、Virginia Pulito、Linda Jolliffe、Peter Cheung、Sally Varga、Mary Evangelisto、Jian Wang

  DOI：10.1021/jm9905918

  日期：2000.6.1

  Beginning from the screening hit and literature alpha(1)-adrenergic compounds, a hybridized basic skeleton A was proposed as the pharmacophore for potent and selective alpha(1a)-AR antagonists. Introduction of a hydroxy group to increase the flexibility afforded B which served as the screening model and resulted in the identification of the second-generation lead 1. Using the Topliss approach, a number of potent and selective alpha(1a)-AR antagonists were discovered. In all cases, binding affinity and selectivity at the alpha(1a)-AR of S-hydroxy enantiomers were higher than those of the R-hydroxy enantiomers. As compared to the des-hydroxy analogues, the S-hydroxy enantiomers had slightly lower binding affinity at alpha(1a)-AR but gained more than 2-fold selectivity for alpha(1a)-AR over alpha(1b)-AR, and 2- to 6-fold selectivity for alpha(1a)-AR over alpha(1d)-AR. They also had less cross activities against a panel of 25-35 peripheral and CNS receptors. The S-hydroxy enantiomers 23 and 24 (K-i = 0.29 nM, 0.33 nM; alpha(1b)/alpha(1a) >5690, >6060; alpha(1d)/alpha(1a) = 186, 158, respectively) were slightly less potent but much more selective at alpha(1a)-AR than tamsulosin (K-i = 0.13 nM, alpha(1d)/alpha(1a)= 14.8, alpha(1d)/alpha(1a) = 1.4). In the functional assay, the S-hydroxy enantiomers 20, 23, and 24 were less potent than tamsulosin in inhibiting contractions of rat prostate tissue but more selective in the inhibition of tissue contractions of rat prostate versus rat aorta. Compound 24 was selected as the development candidate for the treatment of BPH.