1-[(6-methyl-2,2-dioxido-1,2,3-oxathiazin-4-yl)oxy]propan-2-one | 1621619-24-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: 1-[(6-methyl-2,2-dioxido-1,2,3-oxathiazin-4-yl)oxy]propan-2-one
• 英文别名: 1-(6-Methyl-2,2-dioxooxathiazin-4-yl)oxypropan-2-one；1-(6-methyl-2,2-dioxooxathiazin-4-yl)oxypropan-2-one
• CAS: 1621619-24-6
• 化学式: C₇H₉NO₅S
• 分子量: 219.218
• InChiKey: XKYXBFJJUICKDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  90.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  potassium acesulfame 、 一氯丙酮 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以28%的产率得到6-methyl-3-(2-oxopropyl)-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide
  参考文献：
  名称：

  Cyclic tertiary sulfamates: Selective inhibition of the tumor-associated carbonic anhydrases IX and XII by N- and O-substituted acesulfame derivatives

  摘要：

  Carbonic anhydrase (hCA) IX and XII isoforms are over-expressed both in primary and in metastatic cell lines of hypoxic tumors and are innovative targets for cancer diagnosis and treatment. On the basis of the importance of the pharmacophoric sulfamate moiety (bioisostere of the sulfonamide group) present in the structure of recent human CA inhibitors, we designed N-alkylated and O-alkylated derivatives of acesulfame, a cyclic tertiary sulfamate, assessing the inhibitory activity against the ubiquitous isoforms hCA I and II and the cancer-related isoforms hCA IX and XII. All derivatives were nanomolar inhibitors, with some of them possessing an outstanding selectivity towards the tumor-associated hCA IX and/or hCA XII isoforms.

  DOI：

  10.1016/j.ejmech.2014.07.014

文献信息

• Cyclic tertiary sulfamates: Selective inhibition of the tumor-associated carbonic anhydrases IX and XII by N- and O-substituted acesulfame derivatives
  作者：Celeste De Monte、Simone Carradori、Daniela Secci、Melissa D'Ascenzio、Daniela Vullo、Mariangela Ceruso、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2014.07.014

  日期：2014.9

  Carbonic anhydrase (hCA) IX and XII isoforms are over-expressed both in primary and in metastatic cell lines of hypoxic tumors and are innovative targets for cancer diagnosis and treatment. On the basis of the importance of the pharmacophoric sulfamate moiety (bioisostere of the sulfonamide group) present in the structure of recent human CA inhibitors, we designed N-alkylated and O-alkylated derivatives of acesulfame, a cyclic tertiary sulfamate, assessing the inhibitory activity against the ubiquitous isoforms hCA I and II and the cancer-related isoforms hCA IX and XII. All derivatives were nanomolar inhibitors, with some of them possessing an outstanding selectivity towards the tumor-associated hCA IX and/or hCA XII isoforms.