methyl (2R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl-(4-methoxyphenyl)sulfonylamino]propanoate | 1259374-21-4

• 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 (2R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl-(4-methoxyphenyl)sulfonylamino]propanoate
• CAS: 1259374-21-4
• 化学式: C₂₃H₃₉NO₈SSi
• 分子量: 517.716
• InChiKey: FBDDZPJIMLPDSC-AZUAARDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (2R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl-(4-methoxyphenyl)sulfonylamino]propanoate 在 溶剂黄146 、 盐酸羟胺 、 potassium hydroxide 作用下， 以 水 、 甲醇 为溶剂， 反应 19.0h， 以50%的产率得到(2R)-2-[[(2S)-2,3-dihydroxypropyl]-(4-methoxyphenyl)sulfonylamino]-N,3-dihydroxypropanamide
  参考文献：
  名称：

  Structure-based approach to nanomolar, water soluble matrix metalloproteinases inhibitors (MMPIs)

  摘要：

  N-Arylsulfonyl-based MMPs inhibitors (MMPIs) are among the most prominent inhibitors possessing nanomolar affinity. However, their poor bioavailability remains critical for the drug development of this family of molecules. The structural analysis of the complex of NNGH (the most representative member of the family) with MMP-12 provided us with the basis to effectively design simple NNGH analogues with enhanced solubility in water. Following this approach, the sec-butyl residue, not directly involved in the binding with MMP, has been replaced with hydrophilic residues thus yielding new potent inhibitors soluble in water. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.057
• 作为产物：
  描述：

  methyl (2R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(4-methoxyphenyl)sulfonylamino]propanoate 、 (S)-(+)-1,2-异亚丙基甘油 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到methyl (2R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl-(4-methoxyphenyl)sulfonylamino]propanoate
  参考文献：
  名称：

  Structure-based approach to nanomolar, water soluble matrix metalloproteinases inhibitors (MMPIs)

  摘要：

  N-Arylsulfonyl-based MMPs inhibitors (MMPIs) are among the most prominent inhibitors possessing nanomolar affinity. However, their poor bioavailability remains critical for the drug development of this family of molecules. The structural analysis of the complex of NNGH (the most representative member of the family) with MMP-12 provided us with the basis to effectively design simple NNGH analogues with enhanced solubility in water. Following this approach, the sec-butyl residue, not directly involved in the binding with MMP, has been replaced with hydrophilic residues thus yielding new potent inhibitors soluble in water. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.057

文献信息

• Structure-based approach to nanomolar, water soluble matrix metalloproteinases inhibitors (MMPIs)
  作者：Emanuele Attolino、Vito Calderone、Elisa Dragoni、Marco Fragai、Barbara Richichi、Claudio Luchinat、Cristina Nativi

  DOI：10.1016/j.ejmech.2010.09.057

  日期：2010.12

  N-Arylsulfonyl-based MMPs inhibitors (MMPIs) are among the most prominent inhibitors possessing nanomolar affinity. However, their poor bioavailability remains critical for the drug development of this family of molecules. The structural analysis of the complex of NNGH (the most representative member of the family) with MMP-12 provided us with the basis to effectively design simple NNGH analogues with enhanced solubility in water. Following this approach, the sec-butyl residue, not directly involved in the binding with MMP, has been replaced with hydrophilic residues thus yielding new potent inhibitors soluble in water. (C) 2010 Elsevier Masson SAS. All rights reserved.