4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-pyridin-2-yl benzenesulfonamide | 40266-18-0

• 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: 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-pyridin-2-yl benzenesulfonamide
• 英文别名: 4-phthalimido-benzenesulfonic acid-[2]pyridylamide；4-Phthalimido-benzolsulfonsaeure-[2]pyridylamid；4-(1,3-dioxoisoindolin-2-yl)-N-(2-pyridyl)benzenesulfonamide；4-(1,3-dioxoisoindol-2-yl)-N-pyridin-2-ylbenzenesulfonamide
• CAS: 40266-18-0
• 化学式: C₁₉H₁₃N₃O₄S
• 分子量: 379.396
• InChiKey: JMFTYWHOUAWISN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-pyridin-2-yl benzenesulfonamide 在 氢氧化钾 作用下， 生成 N-(4-[2]pyridylsulfamoyl-phenyl)-phthalamic acid
  参考文献：
  名称：

  Picard et al., Journal of the Chemical Society, 1948, p. 821

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苯基邻苯二甲酰亚胺 在 吡啶 、 chlorosulphuric acid 作用下， 生成 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-pyridin-2-yl benzenesulfonamide
  参考文献：
  名称：

  Picard et al., Journal of the Chemical Society, 1948, p. 821

  摘要：

  DOI：

文献信息

• 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。
• Method of preparing sulfonamides
  申请人：AMERICAN CYANAMID CO

  公开号：US02414403A1

  公开（公告）日：1947-01-14
• CONDENSATION OF HETEROCYCLIC AMINES WITH DICARBOXYLIC ACID ANHYDRIDES
  作者：DAVID SHAPIRO、FELIX BERGMANN

  DOI：10.1021/jo01205a012

  日期：1941.9
• 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.