N-(4-phenoxybenzenesulfonyl)-N-{[2-(4-sulfamoylphenyl)ethylcarbamoyl]methyl}-O-benzyl-D-valine | 1092691-02-5

• 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: N-(4-phenoxybenzenesulfonyl)-N-{[2-(4-sulfamoylphenyl)ethylcarbamoyl]methyl}-O-benzyl-D-valine
• 英文别名: benzyl (2R)-3-methyl-2-[[2-oxo-2-[2-(4-sulfamoylphenyl)ethylamino]ethyl]-(4-phenoxyphenyl)sulfonylamino]butanoate
• CAS: 1092691-02-5
• 化学式: C₃₄H₃₇N₃O₈S₂
• 分子量: 679.815
• InChiKey: GMILCRSFZBLJMM-MGBGTMOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  179
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-(4-phenoxybenzenesulfonyl)-N-{[2-(4-sulfamoylphenyl)ethylcarbamoyl]methyl}-O-benzyl-D-valine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、150.0 kPa 条件下， 反应 3.0h， 以92%的产率得到N-(4-phenoxybenzenesulfonyl)-N-{[2-(4-sulfamoylphenyl)ethylcarbamoyl]-methyl}-D-valine
  参考文献：
  名称：

  Dual Inhibitors of Matrix Metalloproteinases and Carbonic Anhydrases: Iminodiacetyl-Based Hydroxamate−Benzenesulfonamide Conjugates

  摘要：

  Matrix metalloproteinases (MMPs) and carbonic anhydrases (CAs) are two classes of zinc enzymes with different roles and catalytic targets, such as the degradation of most of the extracellular matrix (ECM) proteins and the regulation of the CO2/HCO3- equilibrium in the cells, respectively. Both families have isoforms which were proved to be involved in several stages of carcinogenic processes, and so the selective inhibition of these enzymes might be of interest in cancer therapy. We report herein the design, synthesis, and in vitro evaluation of a series Of Compounds possessing the iminodiacetic acid as the main backbone and two functional groups attached, namely, the hydroxamic acid and the arylsulfonamide (ArSO2NH2) moieties, to enable the inhibition of MMPs and CAs, respectively. These compounds were demonstrated to strongly inhibit both MMPs and CAs, some of them from the nanomolar to subnanomolar range. Furthermore, a docking study for MMPs was reported for the most promising compound in order to investigate its binding interactions with the different MMPs.

  DOI：

  10.1021/jm800964f
• 作为产物：
  描述：

  N-(4-phenoxybenzenesulfonyl)-N-hydroxycarbonylmethyl-O-benzyl-D-valine 、 4-(2-氨乙基)苯磺酰胺 在 N-甲基吗啉 、 氯甲酸乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以72%的产率得到N-(4-phenoxybenzenesulfonyl)-N-{[2-(4-sulfamoylphenyl)ethylcarbamoyl]methyl}-O-benzyl-D-valine
  参考文献：
  名称：

  Dual Inhibitors of Matrix Metalloproteinases and Carbonic Anhydrases: Iminodiacetyl-Based Hydroxamate−Benzenesulfonamide Conjugates

  摘要：

  Matrix metalloproteinases (MMPs) and carbonic anhydrases (CAs) are two classes of zinc enzymes with different roles and catalytic targets, such as the degradation of most of the extracellular matrix (ECM) proteins and the regulation of the CO2/HCO3- equilibrium in the cells, respectively. Both families have isoforms which were proved to be involved in several stages of carcinogenic processes, and so the selective inhibition of these enzymes might be of interest in cancer therapy. We report herein the design, synthesis, and in vitro evaluation of a series Of Compounds possessing the iminodiacetic acid as the main backbone and two functional groups attached, namely, the hydroxamic acid and the arylsulfonamide (ArSO2NH2) moieties, to enable the inhibition of MMPs and CAs, respectively. These compounds were demonstrated to strongly inhibit both MMPs and CAs, some of them from the nanomolar to subnanomolar range. Furthermore, a docking study for MMPs was reported for the most promising compound in order to investigate its binding interactions with the different MMPs.

  DOI：

  10.1021/jm800964f