methyl (2S)-2-hydroxy-3-[N-methylsulfonyl-4-[5-(trifluoromethyl)pyridin-2-yl]oxyanilino]propanoate | 1008531-12-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2S)-2-hydroxy-3-[N-methylsulfonyl-4-[5-(trifluoromethyl)pyridin-2-yl]oxyanilino]propanoate
• CAS: 1008531-12-1
• 化学式: C₁₇H₁₇F₃N₂O₆S
• 分子量: 434.393
• InChiKey: HYIQUVZULHOPIT-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-hydroxy-3-[N-methylsulfonyl-4-[5-(trifluoromethyl)pyridin-2-yl]oxyanilino]propanoate 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 N-hydroxy (2S)-2-hydroxy-3-{N-{4-[(5-trifluoromethylpyridin-2-yl)oxy]phenyl},N-methanesulfonylamino}propionamide
  参考文献：
  名称：

  β-N-Biaryl ether sulfonamide hydroxamates as potent gelatinase inhibitors: Part 1. Design, synthesis, and lead identification

  摘要：

  A new series of beta-N-biaryl ether sulfonamide hydroxamates as novel gelatinase inhibitors is described. These compounds exhibit good potency for MMP-2 and MMP-9 without inhibiting MMP-1. The structure-activity relationships (SAR) reveal the biaryl ether type P1' moiety together with methanesulfonamide is the optimal combination that provides inhibitory activity of MMP-9 in the single-digit nanomolar range. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.119
• 作为产物：
  描述：

  N-[4-[5-(trifluoromethyl)pyridin-2-yl]oxyphenyl]methanesulfonamide 、 (2S)-甘油酸甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以72%的产率得到methyl (2S)-2-hydroxy-3-[N-methylsulfonyl-4-[5-(trifluoromethyl)pyridin-2-yl]oxyanilino]propanoate
  参考文献：
  名称：

  Microwave assisted ring-opening of epoxides with N-biaryl sulfonamides in the synthesis of matrix metalloproteinase-9 inhibitors

  摘要：

  A microwave accelerated epoxide ring-opening process with N-biaryl sulfonamides is described. Under this mild, highly efficient condition, an alpha-hydroxy-beta-N-biaryl sulfonamide skeleton is rapidly assembled leading ultimately to a novel series of matrix metalloproteinase-9 inhibitors with single digit nanomolar activities. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.184