Methyl 2-(2-phenylethylsulfonylamino)acetate | 1156840-85-5

• 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: Methyl 2-(2-phenylethylsulfonylamino)acetate
• CAS: 1156840-85-5
• 化学式: C₁₁H₁₅NO₄S
• mdl: MFCD12087365
• 分子量: 257.31
• InChiKey: QUFMGBRHYIGEGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 2-(2-phenylethylsulfonylamino)acetate 在 盐酸羟胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.1h， 生成 N-hydroxy-2-(2-phenylethylsulfonamido)acetamide
  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：

  2-苯基乙磺酸钠 在 4-二甲氨基吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Methyl 2-(2-phenylethylsulfonylamino)acetate
  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

• An efficient and mild oxidative approach from thiols to sulfonyl derivatives with DMSO/HBr
  作者：Hongye Wang、Zhaoting Li、Rongheng Dai、Ning Jiao、Song Song

  DOI：10.1039/d3sc04945k

  日期：——

  A mild and practical method for synthesizing sulfonyl derivatives, which have a wide range of applications in pharmaceuticals, materials, and organic synthesis, was described through the oxidative functionalization of thiols with DMSO/HBr. The simple conditions, low cost and ready availability of DMSO/HBr, as well as the versatility of the transformations, make this strategy very powerful in synthesizing

  通过二甲基亚砜/溴化氢对硫醇进行氧化官能化，描述了一种温和实用的合成磺酰衍生物的方法，该衍生物在药物、材料和有机合成中具有广泛的应用。DMSO/HBr 的简单条件、低成本和易得性，以及转化的多功能性，使得该策略在合成各种磺酰衍生物（包括磺酰胺、磺酰氟、磺酰叠氮化物和磺酸盐）方面非常有效。机理研究表明，DMSO 作为末端氧化剂，HBr 既作为亲核试剂又作为氧化还原介体来转移氧原子。