ethyl 5-(6-nitro-1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)pentanoate | 1242317-07-2

• 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: ethyl 5-(6-nitro-1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)pentanoate
• 英文别名: Ethyl 5-(6-nitro-1,1,3-trioxo-1,2-benzothiazol-2-yl)pentanoate
• CAS: 1242317-07-2
• 化学式: C₁₄H₁₆N₂O₇S
• 分子量: 356.356
• InChiKey: OANHQVIWDHVFHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 5-(6-nitro-1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)pentanoate 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 水 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 12.17h， 生成 N-(2-(5-(hydroxyamino)-5-oxopentyl)-1,1-dioxido-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yl)benzamide
  参考文献：
  名称：

  Design, synthesis and preliminary bioactivity studies of 1,2-dihydrobenzo[d]isothiazol-3-one-1,1-dioxide hydroxamic acid derivatives as novel histone deacetylase inhibitors

  摘要：

  Histone deacetylase (HDAC) is a clinically validated target for antitumor therapy. In order to increase HDAC inhibition and efficiency, we developed a novel series of saccharin hydroxamic acids as potent HDAC inhibitors. Among them, compounds 11e, 11m, 11p exhibited similar or better HDACs inhibitory activity compared with the approved drug SAHA. Further biological evaluation indicated that compound 11m had potent antiproliferative activities against MDA-MB-231 and PC-3. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.045
• 作为产物：
  描述：

  2-甲基-5-硝基苯磺酰胺 在 chromium(VI) oxide 、 硫酸 、 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 ethyl 5-(6-nitro-1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)pentanoate
  参考文献：
  名称：

  Design, synthesis and preliminary bioactivity studies of 1,2-dihydrobenzo[d]isothiazol-3-one-1,1-dioxide hydroxamic acid derivatives as novel histone deacetylase inhibitors

  摘要：

  Histone deacetylase (HDAC) is a clinically validated target for antitumor therapy. In order to increase HDAC inhibition and efficiency, we developed a novel series of saccharin hydroxamic acids as potent HDAC inhibitors. Among them, compounds 11e, 11m, 11p exhibited similar or better HDACs inhibitory activity compared with the approved drug SAHA. Further biological evaluation indicated that compound 11m had potent antiproliferative activities against MDA-MB-231 and PC-3. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.045

文献信息

• Microwave-Assisted Preparation of<i>N</i>-Alkylated Saccharins and Their Reactions with Potassium t-Butoxide
  作者：Žiga Jakopin、Marija Sollner Dolenc

  DOI：10.1080/00397910903267905

  日期：2010.7.27

  A simple and efficient method of N-alkylation, using either conventional heating or microwave irradiation, was applied successfully to the alkylation of several substituted saccharins. Subsequent t-butoxide-induced condensation of these products led to the formation of fused polycyclic sultams, which could be a privileged framework in the field of medicinal chemistry because of their favorable hydrophilic

  使用常规加热或微波辐射的简单有效的 N-烷基化方法已成功应用于几种取代糖精的烷基化。随后的叔丁醇诱导这些产物的缩合导致形成稠合的多环 sultam，由于其有利的亲水性和直接的功能化，这可能是药物化学领域的一个特殊框架。