2-{4-[(3,5-dimethylphenylcarbamoyl)methyl]phenoxy}-2-methyl-butyric acid

• 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: 2-{4-[(3,5-dimethylphenylcarbamoyl)methyl]phenoxy}-2-methyl-butyric acid
• 英文别名: 2-[4-[[(3,5-dimethylanilino)carbonyl]methyl]phenoxy]-2-methylbutanoic acid；2-[4-[2-(3,5-dimethylanilino)-2-oxoethyl]phenoxy]-2-methylbutanoic acid
• 化学式: C₂₁H₂₅NO₄
• 分子量: 355.434
• InChiKey: LKDKURXBSFNRLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙丙昔罗 、 L-丙氨酸甲酯盐酸盐 、 1-羟基苯并三唑一水物 、 N-甲基吗啉 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 2-{4-[(3,5-dimethylphenylcarbamoyl)methyl]phenoxy}-2-methyl-butyric acid 以 N,N-二甲基甲酰胺 为溶剂， 以yield (98%)的产率得到2-(2-{4-[(3,5-Dimethyl-phenylcarbamoyl)-methyl]-phenoxy}-2-methyl-propionylamino)-propionic acid
  参考文献：
  名称：

  Substituted chiral allosteric hemoglobin modifiers

  摘要：

  一种替代手性变构血红蛋白效应物家族可通过降低全血中血红蛋白的氧亲和力，有助于将更多氧气输送到缺氧和缺血组织中。

  公开号：

  US06894185B2
• 作为产物：
  描述：

  1-氨基-3,5-二甲苯 在 sodium hydroxide 作用下， 以 四氢呋喃 、 xylene 为溶剂， 反应 72.25h， 生成 2-{4-[(3,5-dimethylphenylcarbamoyl)methyl]phenoxy}-2-methyl-butyric acid
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Chiral Allosteric Modifiers of Hemoglobin

  摘要：

  A series of allosteric effecters of hemoglobin, 2-(aryloxy)-2-alkanoic acids, was prepared to investigate the effect of the stereocenter on allosteric activity. The chiral analogues were based on the lead compound, RSR13 (3b), with different alkyl/alkanoic and cycloalkyl/cycloalkanoic groups positioned at the acidic chiral center. Of the 23 racemic molecules synthesized, 5 were selected for resolution based on structure-activity relationships. One chiral analogue, (-)( 1R,2R)-1-[4-[[(3,5 -dimethylanilino)carbonyl]methyl]phenoxy]-2-methylcyclopentanecarboxylic acid (11), exhibited greater in vitro activity in hemoglobin solutions than its antipode, racemate, and RSR13. Compound (-)-(LR,2R)-11 was equipotent with RSR13 in whole blood, is a candidate for in vivo animal studies, and if efficacious and safe has a potential for use in humans. In general, it was found that chirality affects allosteric effector activity with measurable differences observed between enantiomers and the racemates.

  DOI：

  10.1021/jm000199q

文献信息

• Mass spectrometric characterization of efaproxiral (RSR13) and its implementation into doping controls using liquid chromatography–atmospheric pressure ionization-tandem mass spectrometry
  作者：Mario Thevis、Oliver Krug、Wilhelm Schänzer

  DOI：10.1002/jms.993

  日期：2006.3

  electrospray ionization (ESI) and tandem mass spectrometry by employing a novel linear ion trap--orbitrap hybrid mass spectrometer--in positive and negative ionization modes. The elimination of 2-methyl acrylic acid (-86 u) has been identified as a major fragmentation process in both charge states. Negative ionization and collision-induced dissociation (CID) caused an additional release of carbon dioxide (-44

  根据世界反兴奋剂机构（WADA），在体育运动中禁止使用Efaproxiral（2- [4-[[（（3,5-二甲基苯胺基羰基）甲基]苯氧基] -2-甲基丙酸。使用电喷雾电离（ESI）和串联质谱法，通过使用新型线性离子阱-轨道阱混合质谱仪- -在正电离和负电离模式下。在两种电荷状态下，消除2-甲基丙烯酸（-86 u）是主要的裂解过程。负离子化和碰撞诱导解离（CID）导致二氧化碳的额外释放（-44 u），正离子化导致甲酸的损失（-46 u）。
• SUBSTITUTED CHIRAL ALLOSTERIC HEMOGLOBIN MODIFIERS
  申请人：VIRGINIA COMMONWEALTH UNIVERSITY

  公开号：EP1206442A1

  公开（公告）日：2002-05-22
• EP1206442A4
  申请人：——

  公开号：EP1206442A4

  公开（公告）日：2004-12-29
• US5290803A
  申请人：——

  公开号：US5290803A

  公开（公告）日：1994-03-01
• US6486342B1
  申请人：——

  公开号：US6486342B1

  公开（公告）日：2002-11-26