(3S)-3-(ethylamino)piperidin-2-one | 1231734-45-4

• 英文名称: (3S)-3-(ethylamino)piperidin-2-one
• CAS: 1231734-45-4
• 化学式: C₇H₁₄N₂O
• 分子量: 142.201
• InChiKey: YNUAVEIQFKABIN-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S)-3-(ethylamino)piperidin-2-one 在 盐酸 作用下， 反应 2.0h， 生成 Nα-Ethyl-Orn-OH
  参考文献：
  名称：

  Inhibitors of N α-acetyl-l-ornithine deacetylase: synthesis, characterization and analysis of their inhibitory potency

  摘要：

  A series of N (alpha)-acyl (alkyl)- and N (alpha)-alkoxycarbonyl-derivatives of l- and d-ornithine were prepared, characterized, and analyzed for their potency toward the bacterial enzyme N (alpha)-acetyl-l-ornithine deacetylase (ArgE). ArgE catalyzes the conversion of N (alpha)-acetyl-l-ornithine to l-ornithine in the fifth step of the biosynthetic pathway for arginine, a necessary step for bacterial growth. Most of the compounds tested provided IC50 values in the mu M range toward ArgE, indicating that they are moderately strong inhibitors. N (alpha)-chloroacetyl-l-ornithine (1g) was the best inhibitor tested toward ArgE providing an IC50 value of 85 mu M while N (alpha)-trifluoroacetyl-l-ornithine (1f), N (alpha)-ethoxycarbonyl-l-ornithine (2b), and N (alpha)-acetyl-d-ornithine (1a) weakly inhibited ArgE activity providing IC50 values between 200 and 410 mu M. Weak inhibitory potency toward Bacillus subtilis-168 for N (alpha)-acetyl-d-ornithine (1a) and N (alpha)-fluoro- (1f), N (alpha)-chloro- (1g), N (alpha)-dichloro- (1h), and N (alpha)-trichloroacetyl-ornithine (1i) was also observed. These data correlate well with the IC50 values determined for ArgE, suggesting that these compounds might be capable of getting across the cell membrane and that ArgE is likely the bacterial enzymatic target.

  DOI：

  10.1007/s00726-009-0326-8
• 作为产物：
  描述：

  C2H5-Orn(Z)-OCH3 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (3S)-3-(ethylamino)piperidin-2-one
  参考文献：
  名称：

  Inhibitors of N α-acetyl-l-ornithine deacetylase: synthesis, characterization and analysis of their inhibitory potency

  摘要：

  A series of N (alpha)-acyl (alkyl)- and N (alpha)-alkoxycarbonyl-derivatives of l- and d-ornithine were prepared, characterized, and analyzed for their potency toward the bacterial enzyme N (alpha)-acetyl-l-ornithine deacetylase (ArgE). ArgE catalyzes the conversion of N (alpha)-acetyl-l-ornithine to l-ornithine in the fifth step of the biosynthetic pathway for arginine, a necessary step for bacterial growth. Most of the compounds tested provided IC50 values in the mu M range toward ArgE, indicating that they are moderately strong inhibitors. N (alpha)-chloroacetyl-l-ornithine (1g) was the best inhibitor tested toward ArgE providing an IC50 value of 85 mu M while N (alpha)-trifluoroacetyl-l-ornithine (1f), N (alpha)-ethoxycarbonyl-l-ornithine (2b), and N (alpha)-acetyl-d-ornithine (1a) weakly inhibited ArgE activity providing IC50 values between 200 and 410 mu M. Weak inhibitory potency toward Bacillus subtilis-168 for N (alpha)-acetyl-d-ornithine (1a) and N (alpha)-fluoro- (1f), N (alpha)-chloro- (1g), N (alpha)-dichloro- (1h), and N (alpha)-trichloroacetyl-ornithine (1i) was also observed. These data correlate well with the IC50 values determined for ArgE, suggesting that these compounds might be capable of getting across the cell membrane and that ArgE is likely the bacterial enzymatic target.

  DOI：

  10.1007/s00726-009-0326-8

文献信息

• US7557110B2
  申请人：——

  公开号：US7557110B2

  公开（公告）日：2009-07-07