(2R)-2-({4-[(benzenesulfonylhydrazono)methyl]benzenesulfonyl}amino)-3-methylbutanoic acid tert-butyl ester | 193810-44-5

• 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: (2R)-2-({4-[(benzenesulfonylhydrazono)methyl]benzenesulfonyl}amino)-3-methylbutanoic acid tert-butyl ester
• CAS: 193810-44-5
• 化学式: C₂₂H₂₉N₃O₆S₂
• 分子量: 495.621
• InChiKey: CHEZQEYUAOZTON-HXUWFJFHSA-N

物化性质

• 沸点：
  622.9±65.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 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：
  0.36
• 拓扑面积：
  131.0
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R)-2-({4-[(benzenesulfonylhydrazono)methyl]benzenesulfonyl}amino)-3-methylbutanoic acid tert-butyl ester 在 三氟乙酸 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (R)-3-Methyl-2-{4-[2-(4-methylsulfanyl-phenyl)-2H-tetrazol-5-yl]-benzenesulfonylamino}-butyric 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：

  D-valine t-butyl ester 在 N-甲基吗啉 、 二甲基硫 、 臭氧 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2R)-2-({4-[(benzenesulfonylhydrazono)methyl]benzenesulfonyl}amino)-3-methylbutanoic acid tert-butyl ester
  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