2-(6-nitro-1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)acetic acid | 178755-56-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(6-nitro-1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)acetic acid
• 英文别名: 6-nitrosaccharine acetic acid；1,2-Benzisothiazole-2(3H)-acetic acid, 6-nitro-3-oxo-, 1,1-dioxide；2-(6-nitro-1,1,3-trioxo-1,2-benzothiazol-2-yl)acetic acid
• CAS: 178755-56-1
• 化学式: C₉H₆N₂O₇S
• mdl: MFCD17967419
• 分子量: 286.222
• InChiKey: HLACATNEENMZSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  146
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(6-nitro-1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)acetic 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31%的产率得到N-hydroxy-2-(6-nitro-1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)acetamide
  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 、 盐酸 、 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 2-(6-nitro-1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)acetic 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

文献信息

• Microwave-assisted diastereoselective two-step three-component synthesis for rapid access to drug-like libraries of substituted 3-amino-β-lactams
  作者：Guido V. Janssen、Joyce A.C. van den Heuvel、Rik P. Megens、Jorg C.J. Benningshof、Huib Ovaa

  DOI：10.1016/j.bmc.2017.11.014

  日期：2018.1

  a robust microwave-assisted synthesis for the diastereoselective generation of 3-saccharinyl-trans-β-lactams is reported. The method is optimised for combinatorial library synthesis in which decoration of the scaffold is varied on both the β-lactam and the saccharine moiety. Within the European Lead Factory (ELF) consortium, a library of 263 compounds was efficiently produced using the developed methodology

  大型多样的化合物库是基于靶标的药物开发的基本要求。在这项工作中，报道了用于3-糖精基-反式-β-内酰胺的非对映选择性生成的稳健的微波辅助合成。该方法针对组合文库合成进行了优化，在该文库中，β-内酰胺和糖精部分的骨架修饰均发生变化。在欧洲铅厂（ELF）联盟中，使用开发的方法有效地生产了263种化合物的库。
• Da Settimo; Primofiore; La Motta, Il Farmaco, 1996, vol. 51, # 4, p. 261 - 267
  作者：Da Settimo、Primofiore、La Motta、Da Settimo、Simorini、Boldrini、Bianchini

  DOI：——

  日期：——
• 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
  作者：Leiqiang Han、Lei Wang、Xuben Hou、Huansheng Fu、Weiguo Song、Weiping Tang、Hao Fang

  DOI：10.1016/j.bmc.2014.01.045

  日期：2014.3

  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.