(R)-2-(N-(4-((1-(1-((2R,3R,4S,5S,6R)-3-fluoro-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-1H-1,2,3-triazol-4-yl)-2,5,8,11-tetraoxatridecan-13-yl)oxy)benzyl)-4-methoxyphenylsulfonamido)-N-hydroxy-3-methylbutanamide | 1378929-02-2

• 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: (R)-2-(N-(4-((1-(1-((2R,3R,4S,5S,6R)-3-fluoro-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-1H-1,2,3-triazol-4-yl)-2,5,8,11-tetraoxatridecan-13-yl)oxy)benzyl)-4-methoxyphenylsulfonamido)-N-hydroxy-3-methylbutanamide
• 英文别名: (2R)-2-[[4-[2-[2-[2-[2-[[1-[(2R,3R,4S,5S,6R)-3-fluoro-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]triazol-4-yl]methoxy]ethoxy]ethoxy]ethoxy]ethoxy]phenyl]methyl-(4-methoxyphenyl)sulfonylamino]-N-hydroxy-3-methylbutanamide
• CAS: 1378929-02-2
• 化学式: C₃₆H₅₂FN₅O₁₄S
• 分子量: 829.898
• InChiKey: HBDUXNUNXGZOCK-VLIRCAPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  57
• 可旋转键数：
  25
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  251
• 氢给体数：
  5
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  丙炔基-四甘醇-甲磺酸酯 在 N-甲基吗啉 、 盐酸 、 sodium tetrahydroborate 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 1-羟基苯并三唑 、 caesium carbonate 、 sodium ascorbate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium bromide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 90.0h， 生成 (R)-2-(N-(4-((1-(1-((2R,3R,4S,5S,6R)-3-fluoro-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-1H-1,2,3-triazol-4-yl)-2,5,8,11-tetraoxatridecan-13-yl)oxy)benzyl)-4-methoxyphenylsulfonamido)-N-hydroxy-3-methylbutanamide
  参考文献：
  名称：

  A New Class of Highly Potent Matrix Metalloproteinase Inhibitors Based on Triazole-Substituted Hydroxamates: (Radio)Synthesis and in Vitro and First in Vivo Evaluation

  摘要：

  In vivo imaging of MMPs is of great (pre)clinical interest and can potentially be realized with modern three-dimensional and noninvasive in vivo molecular imaging techniques such as positron emission tomography (PET). Consequently, MMP inhibitors (MMPIs) radiolabeled with positron emitting nuclides (e.g., F-18) represent a suitable tool for the visualization of activated MMPs with PET. On the basis of our previous work and results regarding radiolabeled and unlabeled derivatives of the nonselective MMPIs, we discovered a new class of fluorinated MMPIs with a triazole-substituted hydroxamate substructure. These novel MMPIs are characterized by an increased hydrophilicity compared with the lead structures and excellent MMP inhibition potencies for MMP-2, MMP-8, MMP-9, and MMP-13 (IC50 = 0.006-107 nM). Therefore, one promising fluorinated triazole-substituted hydroxamate (30b) was selected and resynthesised as its F-18-labeled version to yield the potential PET radioligand [F-18]30b. The biodistribution behavior of this novel compound was investigated with small animal PET.

  DOI：

  10.1021/jm300199g