3-(4-硝基苯氧基)-1,2-苯并噻唑1,1-二氧化物 | 132636-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 3-(4-硝基苯氧基)-1,2-苯并噻唑1,1-二氧化物
• 英文名称: 3-(4-nitro-phenoxy)-benz[d]isothiazole-1,1-dioxide
• 英文别名: 3-(4-Nitro-phenoxy)-benz[d]isothiazol-1,1-dioxid；1,2-Benzisothiazole, 3-(4-nitrophenoxy)-, 1,1-dioxide；3-(4-nitrophenoxy)-1,2-benzothiazole 1,1-dioxide
• CAS: 132636-65-8
• 化学式: C₁₃H₈N₂O₅S
• 分子量: 304.283
• InChiKey: SATYGHGPOCYZFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 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：
  110
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(4-硝基苯氧基)-1,2-苯并噻唑1,1-二氧化物 在 tin(II) chloride dihdyrate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 1-[4-[(1,1-Dioxo-1,2-benzothiazol-3-yl)oxy]phenyl]-3-phenylurea
  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：

  糖精 在 五氯化磷 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 3-(4-硝基苯氧基)-1,2-苯并噻唑1,1-二氧化物
  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

文献信息

• Metal-assisted reactions. Part 20. Catalytic transfer hydrogenolysis of phenolic CO bonds
  作者：Amadeu F. Brigas、Robert A.W. Johnstone

  DOI：10.1016/s0040-4039(00)97960-7

  日期：1990.1

  After conversion of phenols into O-pseudosaccharyl ethers (2) catalytic transfer hydrogenolysis with Pd/C catalyst and sodium phosphinate as hydrogen donor gave arenes (ArH) in good yield. As an example of the application of this reaction in synthesis, oestrone was converted into oestratrienone in a high yielding, one step reaction.

  在苯酚转化为O-伪糖基醚（2）后，使用Pd / C催化剂和次膦酸钠作为氢供体进行催化转移氢解，可得到高产的芳烃（ArH）。作为该反应在合成中的应用的一个实例，雌酮以高产率的一步反应被转化为雌三烯酮。
• Electronic Effects on C—O—C Ether Bonds in 3-Aryloxy Derivatives of Benzisothiazole 1,1-Dioxides: Rapid Ethanolysis of 3-(4-Nitrophenoxy)-1,2-benzisothiazole 1,1-Dioxide, (1), to give 3-Ethoxy-1,2-benzisothiazole 1,1-Dioxide, (2)
  作者：A. F. Brigas、P. M. Goncalves、R. A. W. Johnstone

  DOI：10.1107/s010827019701353x

  日期：1998.2.15

  The bond lengths in the central C-O-C ether linkage of title compound (1), C13H8N2O5S, are comparable with those found in earlier work on similar compounds. However, (1) was found to undergo very easy solvolysis with ethanol to give (2), C9H9NO3S, for which a structure was also determined, but 3-(4-methoxyphenoxy)-1,2-benzisothiazole 1,1-dioxide, (3), did not hydrolyse under the same conditions. If ground-state structures are important for solvolysis, these results suggest that there should be a difference in the corresponding C-O bond lengths for the ethers (1) and (3). Such differences are not observed. The results can be rationalized by supposing that transition-state energies for ethanolysis are more important factors than those of the ground state.
• BRIGAS, AMADEU F.;JOHNSTONE, ROBERT A. W., TETRAHEDRON LETT., 31,(1990) N0, C. 5789-5790
  作者：BRIGAS, AMADEU F.、JOHNSTONE, ROBERT A. W.

  DOI：——

  日期：——