[(S)-2-Methyl-1-(pyridine-2-carbonyl)-propyl]-carbamic acid benzyl ester | 1027054-61-0

• 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: [(S)-2-Methyl-1-(pyridine-2-carbonyl)-propyl]-carbamic acid benzyl ester
• 英文别名: benzyl N-[(2S)-3-methyl-1-oxo-1-pyridin-2-ylbutan-2-yl]carbamate
• CAS: 1027054-61-0
• 化学式: C₁₈H₂₀N₂O₃
• 分子量: 312.368
• InChiKey: XYNMLYOHPBAFKF-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(S)-2-Methyl-1-(pyridine-2-carbonyl)-propyl]-carbamic acid benzyl ester 在 三氟甲磺酸 、 1-羟基苯并三唑 作用下， 以 二氯甲烷 为溶剂， 反应 15.08h， 生成 ((S)-2-Methyl-1-{(S)-2-[(S)-2-methyl-1-(pyridine-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：

  CBZ-L-缬氨酸 在 N-甲基吗啉 、 正丁基锂 、 1-羟基苯并三唑 作用下， 反应 14.92h， 生成 [(S)-2-Methyl-1-(pyridine-2-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

文献信息

• Peptidyl .alpha.-ketoheterocyclic inhibitors of human neutrophil elastase. 2. Effect of varying the heterocyclic ring on in vitro potency
  作者：Philip D. Edwards、Donald J. Wolanin、Donald W. Andisik、Matthew W. Davis

  DOI：10.1021/jm00001a013

  日期：1995.1

  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.