(S)-2-Amino-3-methyl-1-(1-methyl-1H-benzoimidazol-2-yl)-butan-1-one | 1027247-77-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: (S)-2-Amino-3-methyl-1-(1-methyl-1H-benzoimidazol-2-yl)-butan-1-one
• 英文别名: (2S)-2-amino-3-methyl-1-(1-methylbenzimidazol-2-yl)butan-1-one
• CAS: 1027247-77-3
• 化学式: C₁₃H₁₇N₃O
• 分子量: 231.297
• InChiKey: VYKYRRPBQLOEKE-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-L-valyl-L-proline 、 (S)-2-Amino-3-methyl-1-(1-methyl-1H-benzoimidazol-2-yl)-butan-1-one 在 1-羟基苯并三唑 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以56%的产率得到((S)-2-Methyl-1-{(S)-2-[(S)-2-methyl-1-(1-methyl-1H-benzoimidazole-2-carbonyl)-propylcarbamoyl]-pyrrolidine-1-carbonyl}-propyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Peptidyl .alpha.-ketoheterocyclic inhibitors of human neutrophil elastase. 2. Effect of varying the heterocyclic ring on in vitro potency

  摘要：

  A series of peptidyl alpha-ketoheterocycles were synthesized and evaluated for their in vitro inhibition of human neutrophil elastase (HNE). Several heterocycles, including oxazoline and benzoxazole, afforded extremely potent inhibitors of HNE (1p-r) with nanomolar to subnanomolar K-i values. The structure-activity relationships revealed that for compounds with a K-i < 1000 nM potency tends to be positively correlated with the sigma(I) value of the heterocycle. Furthermore, the results in this study support the hypothesis that, in the covalent enzyme-inhibitor adduct, the azole nitrogen atom of the inhibitor heterocycle participates in a hydrogen-bonding interaction with the active-site His-57.

  DOI：

  10.1021/jm00001a013
• 作为产物：
  描述：

  1-甲基苯并咪唑 在 正丁基锂 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (S)-2-Amino-3-methyl-1-(1-methyl-1H-benzoimidazol-2-yl)-butan-1-one
  参考文献：
  名称：

  Peptidyl .alpha.-ketoheterocyclic inhibitors of human neutrophil elastase. 2. Effect of varying the heterocyclic ring on in vitro potency

  摘要：

  A series of peptidyl alpha-ketoheterocycles were synthesized and evaluated for their in vitro inhibition of human neutrophil elastase (HNE). Several heterocycles, including oxazoline and benzoxazole, afforded extremely potent inhibitors of HNE (1p-r) with nanomolar to subnanomolar K-i values. The structure-activity relationships revealed that for compounds with a K-i < 1000 nM potency tends to be positively correlated with the sigma(I) value of the heterocycle. Furthermore, the results in this study support the hypothesis that, in the covalent enzyme-inhibitor adduct, the azole nitrogen atom of the inhibitor heterocycle participates in a hydrogen-bonding interaction with the active-site His-57.

  DOI：

  10.1021/jm00001a013