methyl (R)-3-(N-(4-(p-tolyloxy)phenyl)methylsulfonamido)-2-(((trifluoromethyl)sulfonyl)oxy)propanoate | 1008531-19-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (R)-3-(N-(4-(p-tolyloxy)phenyl)methylsulfonamido)-2-(((trifluoromethyl)sulfonyl)oxy)propanoate
• CAS: 1008531-19-8
• 化学式: C₁₉H₂₀F₃NO₈S₂
• 分子量: 511.497
• InChiKey: KTGISLDMWMKCKR-QGZVFWFLSA-N

物化性质

• 沸点：
  583.9±60.0 °C(predicted)
• 密度：
  1.465±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  116.28
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl (R)-3-(N-(4-(p-tolyloxy)phenyl)methylsulfonamido)-2-(((trifluoromethyl)sulfonyl)oxy)propanoate 在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 以95%的产率得到methyl (S)-2-azido-3-(N-(4-(p-tolyloxy)phenyl)methylsulfonamido)propanoate
  参考文献：
  名称：

  β-N-Biaryl ether sulfonamide hydroxamates as potent gelatinase inhibitors: Part 2. Optimization of α-amino substituents

  摘要：

  The introduction and the optimization of an alpha-amino substituent based on a series of alpha-hydroxy-beta-N-biaryl ether sulfonamide hydroxamates is described. The modification leads to a new series of MMP-2/MMP-9 inhibitors with enhanced inhibitory activities and improved ADME properties. An efficacy study on reducing the ischemia-induced brain edema in the rat transient middle cerebral artery occlusion (tMCAo) model is also demonstrated. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.129
• 作为产物：
  描述：

  、 三氟甲磺酸酐 在 2,6-二甲基吡啶 作用下， 生成 methyl (R)-3-(N-(4-(p-tolyloxy)phenyl)methylsulfonamido)-2-(((trifluoromethyl)sulfonyl)oxy)propanoate
  参考文献：
  名称：

  β-N-Biaryl ether sulfonamide hydroxamates as potent gelatinase inhibitors: Part 2. Optimization of α-amino substituents

  摘要：

  The introduction and the optimization of an alpha-amino substituent based on a series of alpha-hydroxy-beta-N-biaryl ether sulfonamide hydroxamates is described. The modification leads to a new series of MMP-2/MMP-9 inhibitors with enhanced inhibitory activities and improved ADME properties. An efficacy study on reducing the ischemia-induced brain edema in the rat transient middle cerebral artery occlusion (tMCAo) model is also demonstrated. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.129

文献信息

• Microwave assisted ring-opening of epoxides with N-biaryl sulfonamides in the synthesis of matrix metalloproteinase-9 inhibitors
  作者：Shyh-Ming Yang、William V. Murray

  DOI：10.1016/j.tetlet.2007.11.184

  日期：2008.1

  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.