5-nitro-3-(p-tolylamino)benzo[d]isothiazole 1,1-dioxide | 1428132-88-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 5-nitro-3-(p-tolylamino)benzo[d]isothiazole 1,1-dioxide
• 英文别名: 1,2-Benzisothiazol-3-amine, N-(4-methylphenyl)-5-nitro-, 1,1-dioxide；N-(4-methylphenyl)-5-nitro-1,1-dioxo-1,2-benzothiazol-3-amine
• CAS: 1428132-88-0
• 化学式: C₁₄H₁₁N₃O₄S
• 分子量: 317.325
• InChiKey: WIUXIHZIPAONMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-nitro-3-(p-tolylamino)benzo[d]isothiazole 1,1-dioxide 在 ammonium hydroxide 、 sodium dithionite 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 3-N-(4-methylphenyl)-1,1-dioxo-1,2-benzothiazole-3,5-diamine
  参考文献：
  名称：

  Structure-based design and synthesis of novel pseudosaccharine derivatives as antiproliferative agents and kinase inhibitors

  摘要：

  This study is concerned with the implementation of structure-based techniques for the design of new heterocyclic compounds based on pseudosaccharine scaffold with protein kinase inhibition activity. This nucleus was exploited based on the well-known quinazoline core and its interactions with several protein kinases. Two series of compounds employing this new scaffold were synthesized and evaluated at enzymatic and cellular levels. Compound 9b displayed broad spectrum antiproliferative activity on NCI 60-cell lines panel with mean GI(50) of 5.4 mu M. Investigation of the molecular mechanism showed probable inhibitory activity against Src kinase. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.039
• 作为产物：
  描述：

  4-硝基-2-甲苯胺 在 chromium(VI) oxide 、 盐酸 、 五氯化磷 、 硫酸 、 碳酸氢铵 、 sodium nitrite 作用下， 以 1,4-二氧六环 为溶剂， 反应 79.0h， 生成 5-nitro-3-(p-tolylamino)benzo[d]isothiazole 1,1-dioxide
  参考文献：
  名称：

  Structure-based design and synthesis of novel pseudosaccharine derivatives as antiproliferative agents and kinase inhibitors

  摘要：

  This study is concerned with the implementation of structure-based techniques for the design of new heterocyclic compounds based on pseudosaccharine scaffold with protein kinase inhibition activity. This nucleus was exploited based on the well-known quinazoline core and its interactions with several protein kinases. Two series of compounds employing this new scaffold were synthesized and evaluated at enzymatic and cellular levels. Compound 9b displayed broad spectrum antiproliferative activity on NCI 60-cell lines panel with mean GI(50) of 5.4 mu M. Investigation of the molecular mechanism showed probable inhibitory activity against Src kinase. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.039