(S)-2-(4-aminobenzenesulfonylamino)-3-methyl-butyric acid methyl ester | 943252-96-8

• 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: (S)-2-(4-aminobenzenesulfonylamino)-3-methyl-butyric acid methyl ester
• 英文别名: methyl (2S)-2-[(4-aminophenyl)sulfonylamino]-3-methylbutanoate
• CAS: 943252-96-8
• 化学式: C₁₂H₁₈N₂O₄S
• 分子量: 286.352
• InChiKey: OLHIMZQJWWIPKH-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  哌啶 、 (S)-2-(4-aminobenzenesulfonylamino)-3-methyl-butyric acid methyl ester 在 盐酸 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (S)-3-methyl-2-[4-(piperidin-1-ylazo)benzenesulfonylamino]butyric acid methyl ester 、 (S)-3-methyl-2-[4-(piperidin-1-ylazo)benzenesulfonylamino]butyric acid methyl ester
  参考文献：
  名称：

  Investigation into the P₃ Binding Domain of m-Calpain Using Photoswitchable Diazo- and Triazene-dipeptide Aldehydes:  New Anticataract Agents

  摘要：

  The photoswitchable N-terminal diazo and triazene-dipeptide aldehydes 8a-d, 10a,b, and 17a,b present predominantly as the (E)-isomer, which purportedly binds deep in the S-3 pocket of calpain. All compounds are potent inhibitors of m-calpain, with 8b being the most active (IC50 of 35 nM). The diazo-containing inhibitors 8a, 8c, and 10a were irradiated at 340 nm to give a photostationary state enriched in the (Z)-isomer, and in all cases, these were less active. The most water soluble triazene 17a (IC50 of 90 nM) retards calpain-induced cataract formation in lens culture.

  DOI：

  10.1021/jm061455n
• 作为产物：
  描述：

  (S)-2-(4-nitrobenzenesulfonylamino)-3-methyl-butyric acid methyl ester 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以81%的产率得到(S)-2-(4-aminobenzenesulfonylamino)-3-methyl-butyric acid methyl ester
  参考文献：
  名称：

  Investigation into the P₃ Binding Domain of m-Calpain Using Photoswitchable Diazo- and Triazene-dipeptide Aldehydes:  New Anticataract Agents

  摘要：

  The photoswitchable N-terminal diazo and triazene-dipeptide aldehydes 8a-d, 10a,b, and 17a,b present predominantly as the (E)-isomer, which purportedly binds deep in the S-3 pocket of calpain. All compounds are potent inhibitors of m-calpain, with 8b being the most active (IC50 of 35 nM). The diazo-containing inhibitors 8a, 8c, and 10a were irradiated at 340 nm to give a photostationary state enriched in the (Z)-isomer, and in all cases, these were less active. The most water soluble triazene 17a (IC50 of 90 nM) retards calpain-induced cataract formation in lens culture.

  DOI：

  10.1021/jm061455n