2-(4-(4-aminophenylsulfonyl) phenyl)isoindoline-1,3-dione | 149131-31-7

• 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: 2-(4-(4-aminophenylsulfonyl) phenyl)isoindoline-1,3-dione
• 英文别名: 2-{4-[(4-aminophenyl)sulfonyl]phenyl}-1H-isoindole-1,3(2H)-dione；N-(4-sulfanilyl-phenyl)-phthalimide；N-(4-Sulfanilyl-phenyl)-phthalimid；2-[4-(4-Aminophenyl)sulfonylphenyl]isoindoline-1,3-dione；2-[4-(4-aminophenyl)sulfonylphenyl]isoindole-1,3-dione
• CAS: 149131-31-7
• 化学式: C₂₀H₁₄N₂O₄S
• 分子量: 378.408
• InChiKey: VQCKKPRRCMHEMH-UHFFFAOYSA-N

物化性质

• 熔点：
  256-258 °C
• 沸点：
  656.8±65.0 °C(Predicted)
• 密度：
  1.470±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苯酐 、 2-(4-(4-aminophenylsulfonyl) phenyl)isoindoline-1,3-dione 在 溶剂黄146 作用下， 反应 2.0h， 以83%的产率得到N,N'-(4,4'-sulfonyldiphenylene)-bis-(2-phenyl-isoindole-1,3-dione)
  参考文献：
  名称：

  一系列邻苯二甲酰亚胺衍生物的合成及其体外抗结核分枝杆菌活性

  摘要：

  新的邻苯二甲酰亚胺衍生物很容易通过邻苯二甲酸酐和选定的胺的缩合反应以可变的收率（70-90％）来制备。使用Alamar Blue药敏性评估了所有化合物（3a – l）对结核分枝杆菌H 37 Rv的抵抗力。化合物3c，3i和3l的最低抑菌浓度（MIC）分别为3.9、7.8和5.0μg/ mL，可被视为治疗结核病和耐多药结核病的新的先导化合物。

  DOI：

  10.1016/j.bmc.2009.04.042
• 作为产物：
  描述：

  N-[4-(4-nitro-benzenesulfonyl)-phenyl]-phthalimide 在 盐酸 、 甲酸 、 铁粉 作用下， 生成 2-(4-(4-aminophenylsulfonyl) phenyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Therapeutically valuable derivative of sulfones

  摘要：

  公开号：

  US02328548A1

文献信息

• Synthesis, Molecular Docking, Cytotoxicity and Antioxidant Activity Evaluation of Isoindoline-1,3-dione Derivatives
  作者：Palanichamy Santhosh Kumar、Kuruba Bharath Kumar、Asir Obadiah、Suluvoy Jagadish Kumar、Raman Mohanapriya、Arulappan Durairaj、Subramanian Ramanathan、Samuel Vasanthkumar

  DOI：10.14233/ajchem.2019.22185

  日期：2019.10.12

  A variety of amines have been employed to functionalize isobenzofuran-1,3-dione to obtain isoindoline-1,3-dione derivatives in the base free conditions. All the synthesized compounds are screened for their bioactivity through molecular docking, cytotoxicity (against HeLa) and antioxidant activity. ABTS and DPPH are employed to assess the antioxidant activity. Among the synthesized isoindoline-1,3-dione derivatives (3a-k), compound 3e has showed the best antioxidant activity and also exhibited better binding energy when docked with caspase-3 protein. Cytotoxicity of the synthesized compounds was studied against cervical cancer cell line (HeLa) and compound 3e has displayed better activity than other isoindoline derivatives.

  已使用各种胺类化合物对异苯并呋喃-1,3-二酮进行官能化，以在无碱条件下获得异吲哚-1,3-二酮衍生物。通过分子对接、细胞毒性（针对HeLa细胞）和抗氧化活性对所有合成的化合物进行生物活性筛选。ABTS和DPPH用于评估抗氧化活性。在合成的异吲哚-1,3-二酮衍生物（3a-k）中，化合物3e表现出最佳的抗氧化活性，并且在与caspase-3蛋白对接时显示出更好的结合能。对合成的化合物针对宫颈癌细胞系（HeLa）的细胞毒性进行了研究，化合物3e显示出比其他异吲哚衍生物更好的活性。
• 11. Carboxylic acid derivatives of 4 : 4′-diaminodiphenylsulphone
  作者：W. H. Gray、B. C. Platt

  DOI：10.1039/jr9420000042

  日期：——
• Synthesis and evaluation of novel dapsone–thalidomide hybrids for the treatment of type 2 leprosy reactions
  作者：Paulo Renato Yamasaki、Dejair Caetano do Nascimento、Rafael Consolin Chelucci、Andréa de Faria Fernandes Belone、Patrícia Sammarco Rosa、Suzana Madeira Diório、Thais Regina Ferreira de Melo、Karina Pereira Barbieri、Marisa Campos Polési Placeres、Iracilda Zepone Carlos、Man Chin Chung、Jean Leandro dos Santos

  DOI：10.1016/j.bmcl.2014.05.017

  日期：2014.7

  We synthesized a series of novel dapsone-thalidomide hybrids (3a-i) by molecular hybridization and evaluated their potential for the treatment of type 2 leprosy reactions. All of the compounds had analgesic properties. Compounds 3c and 3h were the most active antinociceptive compounds and reduced acetic acid-induced abdominal constrictions by 49.8% and 39.1%, respectively. The hybrid compounds also reduced tumor necrosis factor-alpha levels in lipopolysaccharide-stimulated L929 cells. Compound 3i was the most active compound; at concentrations of 15.62 and 125 mu M, compound 3i decreased tumor necrosis factor-alpha levels by 86.33% and 87.80%, respectively. In nude mice infected with Mycobacterium leprae in vivo, compound 3i did not reduce the number of bacilli compared with controls. Compound 3i did not have mutagenic effects in Salmonella typhimurium strains TA100 and TA102, with or without metabolic activation (S9 mixture). Our results indicate that compound 3i is a novel lead compound for the treatment of type 2 leprosy reactions. (C) 2014 Elsevier Ltd. All rights reserved.
• Therapeutically valuable derivative of sulfones
  申请人：SCHERING CORP

  公开号：US02328548A1

  公开（公告）日：1943-09-07
• Synthesis and in vitro anti Mycobacterium tuberculosis activity of a series of phthalimide derivatives
  作者：Jean L. Santos、Paulo R. Yamasaki、Chung Man Chin、Célio H. Takashi、Fernando R. Pavan、Clarice Q.F. Leite

  DOI：10.1016/j.bmc.2009.04.042

  日期：2009.6

  New phthalimide derivatives were easily prepared through condensation of phthalic anhydride and selected amines with variable yields (70–90%). All compounds (3a–l) were evaluated against Mycobacterium tuberculosis H37Rv using Alamar Blue susceptibility. The compounds 3c, 3i, and 3l have the minimum inhibitory concentrations (MICs) of 3.9, 7.8, and 5.0 μg/mL, respectively, and could be considered new

  新的邻苯二甲酰亚胺衍生物很容易通过邻苯二甲酸酐和选定的胺的缩合反应以可变的收率（70-90％）来制备。使用Alamar Blue药敏性评估了所有化合物（3a – l）对结核分枝杆菌H 37 Rv的抵抗力。化合物3c，3i和3l的最低抑菌浓度（MIC）分别为3.9、7.8和5.0μg/ mL，可被视为治疗结核病和耐多药结核病的新的先导化合物。