3-(1,1-dioxido-3-oxo-6-(3,4,5-trimethoxybenzamido)benzo[d]isothiazol-2(3H)-yl)propanoic acid | 1569314-57-3

• 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: 3-(1,1-dioxido-3-oxo-6-(3,4,5-trimethoxybenzamido)benzo[d]isothiazol-2(3H)-yl)propanoic acid
• CAS: 1569314-57-3
• 化学式: C₂₀H₂₀N₂O₉S
• 分子量: 464.453
• InChiKey: AMYMQTBNTMRHKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  148.54
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-(1,1-dioxido-3-oxo-6-(3,4,5-trimethoxybenzamido)benzo[d]isothiazol-2(3H)-yl)propanoic acid 在 三乙胺 、 氯甲酸异丁酯 、 盐酸羟胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.17h， 以43%的产率得到N-(2-(3-(hydroxyamino)-3-oxopropyl)-1,1-dioxido-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yl)-3,4,5-trimethoxybenzamide
  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：

  6-硝基-1,2-苯并异噻唑啉-3-酮 1,1-二氧化物 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 20.0~100.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 生成 3-(1,1-dioxido-3-oxo-6-(3,4,5-trimethoxybenzamido)benzo[d]isothiazol-2(3H)-yl)propanoic acid
  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