2-[4-[[(3,5-dimethylanilino)carbonyl]methyl]phenoxy]-3-methoxy-2-methylpropanoic 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-dimethylanilino)carbonyl]methyl]phenoxy]-3-methoxy-2-methylpropanoic acid
• 英文别名: 2-[4-[2-(3,5-Dimethylanilino)-2-oxoethyl]phenoxy]-3-methoxy-2-methylpropanoic acid
• 化学式: C₂₁H₂₅NO₅
• 分子量: 371.433
• InChiKey: QBPSDADGAHTBDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 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-dimethylanilino)carbonyl]methyl]phenoxy]-3-methoxy-2-methylpropanoic 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

• Substituted chiral allosteric hemoglobin modifiers
  申请人：Virginia Commonwealth University

  公开号：US06486342B1

  公开（公告）日：2002-11-26

  A family of substituted chiral allosteric effectors of hemoglobin is useful for delivering more oxygen to hypoxic and ischemic tissues by reducing the oxygen affinity of hemoglobin in whole blood.

  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，有助于向缺氧和缺血组织输送更多氧气。
• 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
• US6486342B1
  申请人：——

  公开号：US6486342B1

  公开（公告）日：2002-11-26
• US6894185B2
  申请人：——

  公开号：US6894185B2

  公开（公告）日：2005-05-17