3-Isothiazolidinecarboxylic acid, 2-[2-(4-hydroxyphenyl)ethyl]-, methylester, 1,1-dioxide | 409107-92-2

• 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: 3-Isothiazolidinecarboxylic acid, 2-[2-(4-hydroxyphenyl)ethyl]-, methylester, 1,1-dioxide
• 英文别名: 2-[2-(4-Hydroxy-phenyl)-ethyl]-1,1-dioxo-1λ⁶-isothiazolidine-3-carboxylic acid methyl ester
• CAS: 409107-92-2
• 化学式: C₁₃H₁₇NO₅S
• 分子量: 299.348
• InChiKey: CTAHDDRCSOFHBH-UHFFFAOYSA-N

物化性质

• 沸点：
  484.1±55.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.51
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  83.91
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-Isothiazolidinecarboxylic acid, 2-[2-(4-hydroxyphenyl)ethyl]-, methylester, 1,1-dioxide 在 氢氧化钾 、 羟胺 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 N-hydroxy-2-(2-{4-[(2-methyl-4-quinolinyl)methoxy]phenyl}ethyl)-3-isothiazolidinecarboxamide 1,1-dioxide
  参考文献：
  名称：

  Conversion of potent MMP inhibitors into selective TACE inhibitors

  摘要：

  Novel sultam hydroxamates with potent MMP activity were transformed into potent TACE inhibitors, lacking MMP activity. To accomplish this we relied on structural differences between the MMP and TACE Sl' pockets and the known advantageous tit of a 2-methyl-4-quinolinylmethoxyphenyl group into this region. From this approach, compound 7d was identified as a potent TACE inhibitor (IC50 = 3.7 nM) that lacked MMP-1, -2, -9, and -13 activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.078
• 作为产物：
  描述：

  1-(2-溴乙基)-4-(苯基甲氧基)苯 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-Isothiazolidinecarboxylic acid, 2-[2-(4-hydroxyphenyl)ethyl]-, methylester, 1,1-dioxide
  参考文献：
  名称：

  Conversion of potent MMP inhibitors into selective TACE inhibitors

  摘要：

  Novel sultam hydroxamates with potent MMP activity were transformed into potent TACE inhibitors, lacking MMP activity. To accomplish this we relied on structural differences between the MMP and TACE Sl' pockets and the known advantageous tit of a 2-methyl-4-quinolinylmethoxyphenyl group into this region. From this approach, compound 7d was identified as a potent TACE inhibitor (IC50 = 3.7 nM) that lacked MMP-1, -2, -9, and -13 activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.078