(3S)-L-valine-(4S)-methylsuccinimide | 124731-95-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S)-L-valine-(4S)-methylsuccinimide
• 英文别名: (3R,4S)-3-[(2S)-2-amino-3-methylbutanoyl]-4-methylpyrrolidine-2,5-dione
• CAS: 124731-95-9
• 化学式: C₁₀H₁₆N₂O₃
• 分子量: 212.249
• InChiKey: XQPITZOBPSWQLW-XVMARJQXSA-N

物化性质

• 沸点：
  390.9±37.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  89.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S)-L-valine-(4S)-methylsuccinimide 在 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.5h， 生成 (3S)-β-phenylalanine-L-valine-(4S)-methylsuccinimide
  参考文献：
  名称：

  Design, Synthesis, and Antibacterial Properties of Dual-Ligand Inhibitors of Acetyl-CoA Carboxylase

  摘要：

  There is an urgent demand for the development of new antibiotics due to the increase in drug-resistant pathogenic bacteria. A novel target is the multifunctional enzyme acetyl-CoA carboxylase (ACC), which catalyzes the first committed step in fatty acid synthesis and consists of two enzymes: biotin carboxylase and carboxyltransferase. Covalently attaching known inhibitors against these enzymes with saturated hydrocarbon linkers of different lengths generated dual-ligand inhibitors. Kinetic results revealed that the dual-ligands inhibited the ACC complex in the nanomolar range. Microbiology assays showed that the dual-ligand with a 15-carbon linker did not exhibit any antibacterial activity, while the dual-ligand with a 7-carbon linker displayed broad-spectrum antibacterial activity as well as a decreased susceptibility in the development of bacterial resistance. These results suggest that the properties of the linker are vital for antibacterial activity and show how inhibiting two different enzymes with the same compound increases the overall potency while also impeding the development of resistance.

  DOI：

  10.1021/jm501082n
• 作为产物：
  描述：

  (S)-methylsuccinic anhydride 在 5%-palladium/activated carbon 、 氢气 、 三乙胺 、 2-溴苯乙酮 、 N,N'-羰基二咪唑 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 7.25h， 生成 (3S)-L-valine-(4S)-methylsuccinimide
  参考文献：
  名称：

  Design, Synthesis, and Antibacterial Properties of Dual-Ligand Inhibitors of Acetyl-CoA Carboxylase

  摘要：

  There is an urgent demand for the development of new antibiotics due to the increase in drug-resistant pathogenic bacteria. A novel target is the multifunctional enzyme acetyl-CoA carboxylase (ACC), which catalyzes the first committed step in fatty acid synthesis and consists of two enzymes: biotin carboxylase and carboxyltransferase. Covalently attaching known inhibitors against these enzymes with saturated hydrocarbon linkers of different lengths generated dual-ligand inhibitors. Kinetic results revealed that the dual-ligands inhibited the ACC complex in the nanomolar range. Microbiology assays showed that the dual-ligand with a 15-carbon linker did not exhibit any antibacterial activity, while the dual-ligand with a 7-carbon linker displayed broad-spectrum antibacterial activity as well as a decreased susceptibility in the development of bacterial resistance. These results suggest that the properties of the linker are vital for antibacterial activity and show how inhibiting two different enzymes with the same compound increases the overall potency while also impeding the development of resistance.

  DOI：

  10.1021/jm501082n

文献信息

• [DE] ARYLAMIDE<br/>[EN] ARYLAMIDES<br/>[FR] ARYLAMIDES
  申请人：BAYER HEALTHCARE AG

  公开号：WO2004020432A1

  公开（公告）日：2004-03-11

  Die vorliegende Erfindung betrifft Verbindungen der Formel,(I), Verfahren zur ihrer Herstellung, sie umfassende pharmazeutische Zusammensetzungen sowie ihre Verwendung bei der Behandlung und/oder Prophylaxe von Erkrankungen bei Menschen oder Tieren, insbesondere bakteriellen Infektionskrankheiten.

  本发明涉及公式(I)的化合物，其制备方法，包括它们的药用组合物以及它们在治疗和/或预防人类或动物疾病，特别是细菌感染疾病方面的用途。
• A convenient diastereoselective total synthesis of andrimid
  作者：AV Rama Rao、A.K. Singh、Ch.V.N.S. Varaprasad

  DOI：10.1016/s0040-4039(00)92179-8

  日期：1991.1

  A convenient diastereoselective synthesis of andrimid was accomplished in a straightforward approach and also several β-substituted cyclic imides were prepared in a facile manner.

  以简单的方法完成了对芳族化合物的便利的非对映选择性合成，并且还以简便的方式制备了几种β-取代的环酰亚胺。
• Stereocontrolled synthesis of andrimid and a structural requirement for the activity
  作者：William McWhorter、Andreas Fredenhagen、Koji Nakanishi、Hajime Komura

  DOI：10.1039/c39890000299

  日期：——

  Total synthesis of an antibiotic Andrimid was accomplished stereospecifically; it was shown that the chiralities at C-3 and C-4 should be R and S, respectively, and the presence of the (4S)-methyl group is important for the activity.

  抗生素Andrimid的全合成是立体定向完成的。结果表明，C-3和C-4的手性分别应为R和S，并且（4 S）-甲基的存在对于该活性很重要。
• [DE] ZIMTSÄUREAMIDE<br/>[EN] CINNAMIC ACID AMIDES<br/>[FR] AMIDES D'ACIDE CINNAMIQUE
  申请人：BAYER AG

  公开号：WO2003091212A1

  公开（公告）日：2003-11-06

  Die vorliegende Erfindung betrifft Verbindungen, Verfahren zur ihrer Herstellung, sie umfassende pharmazeutische Zusammensetzungen sowie ihre Verwendung bei der Behandlung und/oder Prophylaxe von Erkrankungen bei Menschen oder Tieren, insbesondere bakteriellen Infektionskrankheiten.

  本发明涉及连接件，其制造方法，包括药物组合物以及它们在人类或动物的治疗和/或预防疾病中的使用，特别是细菌感染疾病。
• Derivatives of andrimide and moiramide b having antibacterial properties
  申请人：Brunner Nina

  公开号：US20050080129A1

  公开（公告）日：2005-04-14

  The invention relates to compounds of general formula (I), to a method for the production thereof, to pharmaceutical compositions containing them, and to their use in the treatment and/or prophlaxis of diseases in humans or animals, diseases. The compounds are derivatives of the natural substances andrimide and moiramide B.

  本发明涉及一般式(I)的化合物，其生产方法，含有它们的制药组合物，以及它们在人类或动物疾病的治疗和/或预防中的使用。这些化合物是天然物质andrimide和moiramide B的衍生物。