4-{4-[(R)-2-(1H-Indol-3-yl)-1-methoxycarbonyl-ethylsulfamoyl]-phenylethynyl}-benzoic acid | 1026920-55-7

• 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: 4-{4-[(R)-2-(1H-Indol-3-yl)-1-methoxycarbonyl-ethylsulfamoyl]-phenylethynyl}-benzoic acid
• 英文别名: 4-[2-[4-[[(2R)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl]sulfamoyl]phenyl]ethynyl]benzoic acid
• CAS: 1026920-55-7
• 化学式: C₂₇H₂₂N₂O₆S
• 分子量: 502.547
• InChiKey: LPAVCRKSEFWLTO-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-{4-[(R)-2-(1H-Indol-3-yl)-1-methoxycarbonyl-ethylsulfamoyl]-phenylethynyl}-benzoic acid 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 4-{4-[(R)-1-Carboxy-2-(1H-indol-3-yl)-ethylsulfamoyl]-phenylethynyl}-benzoic acid
  参考文献：
  名称：

  Highly Selective and Orally Active Inhibitors of Type IV Collagenase (MMP-9 and MMP-2):  N-Sulfonylamino Acid Derivatives

  摘要：

  Various N-sulfonylamino acid derivatives were synthesized and evaluated for their in vitro and in vivo activities to inhibit type IV collagenase (MMP-9 and MMP-2). When the amino acid residue and the sulfonamide moiety were modified, their inhibitory activities were greatly affected by the structure of the sulfonamide moiety. A series of aryl sulfonamide derivatives containing biaryl, tetrazole, amide, and triple bond were found to be potent and highly selective inhibitors of MMP-9 and MMP-2 In addition, these compounds were orally active in animal models of tumor growth and metastasis. These results revealed the potential of the N-sulfonylamino acid derivatives as a new type of candidate drug for the treatment of cancer.

  DOI：

  10.1021/jm9707582
• 作为产物：
  描述：

  4-碘苯磺酰氯 、 alkaline earth salt of/the/ methylsulfuric acid 在 N-甲基吗啉 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4-{4-[(R)-2-(1H-Indol-3-yl)-1-methoxycarbonyl-ethylsulfamoyl]-phenylethynyl}-benzoic acid
  参考文献：
  名称：

  Highly Selective and Orally Active Inhibitors of Type IV Collagenase (MMP-9 and MMP-2):  N-Sulfonylamino Acid Derivatives

  摘要：

  Various N-sulfonylamino acid derivatives were synthesized and evaluated for their in vitro and in vivo activities to inhibit type IV collagenase (MMP-9 and MMP-2). When the amino acid residue and the sulfonamide moiety were modified, their inhibitory activities were greatly affected by the structure of the sulfonamide moiety. A series of aryl sulfonamide derivatives containing biaryl, tetrazole, amide, and triple bond were found to be potent and highly selective inhibitors of MMP-9 and MMP-2 In addition, these compounds were orally active in animal models of tumor growth and metastasis. These results revealed the potential of the N-sulfonylamino acid derivatives as a new type of candidate drug for the treatment of cancer.

  DOI：

  10.1021/jm9707582