2-(1,3-Dioxaindan-5-yl)ethane-1-sulfonylchloride | 1017125-38-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-(1,3-Dioxaindan-5-yl)ethane-1-sulfonylchloride
• 英文别名: 2-(1,3-benzodioxol-5-yl)ethanesulfonyl chloride
• CAS: 1017125-38-0
• 化学式: C₉H₉ClO₄S
• mdl: MFCD09886672
• 分子量: 248.687
• InChiKey: QARVHGABHYYJGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1,3-Dioxaindan-5-yl)ethane-1-sulfonylchloride 在 4-二甲氨基吡啶 、 盐酸羟胺 、 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.1h， 生成 2-(2-(benzo[d][1,3]dioxol-5-yl)ethylsulfonamido)-N-hydroxyacetamide
  参考文献：
  名称：

  Discovery of a New Class of Potent MMP Inhibitors by Structure-Based Optimization of the Arylsulfonamide Scaffold

  摘要：

  A new class of potent matrix metalloproteinase (MMP) inhibitors designed by structure-based optimization of the well-known arylsulfonamide scaffold is presented. Molecules show an ethylene linker connecting the sulfonamide group with P1' aromatic portion and a D-proline residue bearing the zinc-binding group. The affinity improvement providing by these modifications led us to discover a nanomolar MMP inhibitor bearing a carboxylate moiety as zinc-binding group, which might be a promising lead molecule. Notably, a significant selectivity for MMP-8, MMP-12, and MMP-13 was observed with respect to MMP-1 and MMP-7.

  DOI：

  10.1021/ml300446a
• 作为产物：
  描述：

  5-(2-bromoethyl)-1,3-benzodioxole 在 氯化亚砜 、 四丁基碘化铵 、 sodium sulfite 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(1,3-Dioxaindan-5-yl)ethane-1-sulfonylchloride
  参考文献：
  名称：

  Discovery of a New Class of Potent MMP Inhibitors by Structure-Based Optimization of the Arylsulfonamide Scaffold

  摘要：

  A new class of potent matrix metalloproteinase (MMP) inhibitors designed by structure-based optimization of the well-known arylsulfonamide scaffold is presented. Molecules show an ethylene linker connecting the sulfonamide group with P1' aromatic portion and a D-proline residue bearing the zinc-binding group. The affinity improvement providing by these modifications led us to discover a nanomolar MMP inhibitor bearing a carboxylate moiety as zinc-binding group, which might be a promising lead molecule. Notably, a significant selectivity for MMP-8, MMP-12, and MMP-13 was observed with respect to MMP-1 and MMP-7.

  DOI：

  10.1021/ml300446a

文献信息

• Discovery of a New Class of Potent MMP Inhibitors by Structure-Based Optimization of the Arylsulfonamide Scaffold
  作者：Mattia Mori、Assunta Massaro、Vito Calderone、Marco Fragai、Claudio Luchinat、Alessandro Mordini

  DOI：10.1021/ml300446a

  日期：2013.6.13

  A new class of potent matrix metalloproteinase (MMP) inhibitors designed by structure-based optimization of the well-known arylsulfonamide scaffold is presented. Molecules show an ethylene linker connecting the sulfonamide group with P1' aromatic portion and a D-proline residue bearing the zinc-binding group. The affinity improvement providing by these modifications led us to discover a nanomolar MMP inhibitor bearing a carboxylate moiety as zinc-binding group, which might be a promising lead molecule. Notably, a significant selectivity for MMP-8, MMP-12, and MMP-13 was observed with respect to MMP-1 and MMP-7.