(2S)-1-phenyl-3-methyl-2-amino-1-butanone | 742105-42-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-1-phenyl-3-methyl-2-amino-1-butanone
• 英文别名: (2S)-2-amino-3-methyl-1-phenylbutan-1-one
• CAS: 742105-42-6
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: DGSKMKVBPWZYGE-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-L-valyl-L-proline 、 (2S)-1-phenyl-3-methyl-2-amino-1-butanone 在 1-羟基苯并三唑 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以66%的产率得到{(S)-1-[(S)-2-((S)-1-Benzoyl-2-methyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-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-valine methoxymethylamide 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 (2S)-1-phenyl-3-methyl-2-amino-1-butanone
  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

• Cis-epoxide derivate useful as irreversible HIV protease inhibitor and process for its preparation
  申请人：LG Chemical Limited

  公开号：EP0770606A1

  公开（公告）日：1997-05-02

  The present invention relates to a novel compound of formula (I) and pharmaceutically acceptable salts, hydrates and solvates thereof which is an irreversible HIV protease inhibitor; a process for the preparation thereof; and a pharmaceutical composition containing the compound as an active ingredient which is useful for treating or preventing diseases caused by HIV infection.

  本发明涉及一种新型公式（I）的化合物及其药学上可接受的盐、水合物和溶剂化物，该化合物是一种不可逆的HIV蛋白酶抑制剂；其制备方法；以及含有该化合物作为活性成分的制药组合物，该组合物可用于治疗或预防由HIV感染引起的疾病。
• Novel inhibitors of Hepatitis C virus NS3 protease
  申请人：Bogen L. Stephane

  公开号：US20070142301A1

  公开（公告）日：2007-06-21

  The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.
• US5773468A
  申请人：——

  公开号：US5773468A

  公开（公告）日：1998-06-30
• US7205330B2
  申请人：——

  公开号：US7205330B2

  公开（公告）日：2007-04-17
• US7423058B2
  申请人：——

  公开号：US7423058B2

  公开（公告）日：2008-09-09