缬氨酸N-甲氧基酰胺 | 145373-89-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 缬氨酸N-甲氧基酰胺
• 英文名称: Valine N-methoxyamide
• 英文别名: 2-amino-N-methoxy-3-methylbutanamide
• CAS: 145373-89-3
• 化学式: C₆H₁₄N₂O₂
• 分子量: 146.189
• InChiKey: MQVRCWKRJUCDQA-UHFFFAOYSA-N

物化性质

• 密度：
  1.013±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  缬氨酸N-甲氧基酰胺 在 氢氧化钾 、 苯甲醛 作用下， 生成 L-缬氨酸 、
  参考文献：
  名称：

  Synthesis of racemic .alpha.-amino carboxamides via Lewis acid-mediated reactions of .alpha.-methoxyglycinamide derivatives with allylsilanes: enzymic resolution to optically active .alpha.-amino acids

  摘要：

  A short and expedient synthetic route to optically active, saturated and gamma,delta-unsaturated alpha-amino acids is reported. The key step is a BF3.OEt2-mediated reaction of allylsilanes with N-(alkoxycarbonyl)-alpha-methoxyglycinamides 11-15, leading to the corresponding gamma,delta-unsaturated alpha-aminocarboxamides. The genuine S(N)1-character of this process with iminium ion 6 as intermediate is proven in the case of the glycine ester 10. Thus, reaction of enzymatically resolved 10 with pi-nucleophiles leads to racemic products. The most useful iminium precursors are the N-methoxyamides 12-14 providing good yields of coupling products. The most convenient N-protective group is the allyloxycarbonyl group. Deprotection proceeds via a Pd(0)-catalyzed transprotection to the corresponding BOC-protected analogues. Four examples of the enzymatic resolution of alpha-amino carboxamides, by using an L-specific aminopeptidase from Pseudomonas putida, are described in detail. Most notably, secondary N-methoxyamides are good substrates for the enzyme to provide the desired a-amino acids in high optical purity.

  DOI：

  10.1021/jo00051a019
• 作为产物：
  描述：

  N-(Benzyloxycarbonyl)valine N-methoxyamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以100%的产率得到缬氨酸N-甲氧基酰胺
  参考文献：
  名称：

  Synthesis of racemic .alpha.-amino carboxamides via Lewis acid-mediated reactions of .alpha.-methoxyglycinamide derivatives with allylsilanes: enzymic resolution to optically active .alpha.-amino acids

  摘要：

  A short and expedient synthetic route to optically active, saturated and gamma,delta-unsaturated alpha-amino acids is reported. The key step is a BF3.OEt2-mediated reaction of allylsilanes with N-(alkoxycarbonyl)-alpha-methoxyglycinamides 11-15, leading to the corresponding gamma,delta-unsaturated alpha-aminocarboxamides. The genuine S(N)1-character of this process with iminium ion 6 as intermediate is proven in the case of the glycine ester 10. Thus, reaction of enzymatically resolved 10 with pi-nucleophiles leads to racemic products. The most useful iminium precursors are the N-methoxyamides 12-14 providing good yields of coupling products. The most convenient N-protective group is the allyloxycarbonyl group. Deprotection proceeds via a Pd(0)-catalyzed transprotection to the corresponding BOC-protected analogues. Four examples of the enzymatic resolution of alpha-amino carboxamides, by using an L-specific aminopeptidase from Pseudomonas putida, are described in detail. Most notably, secondary N-methoxyamides are good substrates for the enzyme to provide the desired a-amino acids in high optical purity.

  DOI：

  10.1021/jo00051a019

文献信息

• Quinazoline derivatives useful in cancer treatment
  申请人：Mallams K. Alan

  公开号：US20070015774A1

  公开（公告）日：2007-01-18

  The present invention provides compounds of Formula I (wherein R 1 , R 2 , R 3 , L, and X are as defined herein). or a pharmaceutically acceptable salt, solvate or ester thereof. The present invention also provides compositions comprising these compounds that are useful for treating cellular proliferative diseases, disorders associated with activity of mutants of p53, or in causing apoptosis of cancer cells.

  本发明提供了式I的化合物（其中R1、R2、R3、L和X如本文所定义）。或其药用可接受的盐、溶剂或酯。本发明还提供了包含这些化合物的组合物，用于治疗细胞增殖性疾病、与p53突变体活性有关的疾病，或导致癌细胞凋亡。
• QUINAZOLINE DERIVATIVES USEFUL IN CANCER TREATMENT
  申请人：Schering Corporation

  公开号：EP1915351A1

  公开（公告）日：2008-04-30
• [EN] QUINAZOLINE DERIVATIVES USEFUL IN CANCER TREATMENT<br/>[FR] DERIVEES DE QUINAZOLINE UTILES POUR LE TRAITEMENT DU CANCER
  申请人：SCHERING CORP

  公开号：WO2007011618A1

  公开（公告）日：2007-01-25

  [EN] The present invention provides compounds of Formula (I) (wherein R¹, R², R³, L, and X are as defined herein), or a pharmaceutically acceptable salt, solvate or ester thereof. The present invention also provides compositions comprising these compounds that are useful for treating cellular proliferative diseases, disorders associated with activity of mutants of p53, or in causing apoptosis of cancer cells.
  [FR] Composés de formule I (R¹, R², R³, L, et X sont tels que définis dans la description), y compris un sel, solvate ou ester correspondant. Egalement, compositions renfermant ces composés, utiles pour traiter des maladies liées à la prolifération cellulaire, ou des troubles associés à l'activité de mutants de p53, ou pour induire l'apoptose des cellules cancéreuses.
• [EN] QUINAZOLINE DERIVATIVES USEFUL IN CANCER TREATMENT<br/>[FR] DERIVES DE QUINAZOLINE UTILES POUR TRAITER LE CANCER
  申请人：SCHERING CORP

  公开号：WO2007011623A1

  公开（公告）日：2007-01-25

  [EN] The present invention provides compounds of Formula I (wherein X, m, R¹, R², R³, and R⁴ are as defined herein), or a pharmaceutically acceptable salt, solvate or ester thereof. The present invention also provides compositions comprising these compounds that are useful for treating cellular proliferative diseases, disorders associated with activity of mutants of p53, or in causing apoptosis of cancer cells.
  [FR] La présente invention concerne des composés de formule I (dans laquelle X, m, R¹, R², R³, et R⁴ sont tels que définis dans l'invention), ou un sel, solvate ou ester de ceux-ci, acceptable d'un point de vue pharmaceutique. L'invention a également pour objet des compositions comprenant ces composés, utiles pour traiter des troubles de prolifération cellulaire, des troubles associés à l'activité de formes mutantes de p53, ou pour provoquer l'apoptose de cellules cancéreuses.