(+)-2-[4-[[(3,5-dimethylanilino)carbonyl]methyl]phenoxy]-butanoic Acid | 321853-38-7

• 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]-butanoic Acid
• 英文别名: 2-[4-[2-(3,5-dimethylanilino)-2-oxoethyl]phenoxy]butanoic acid
• CAS: 321853-38-7；321853-51-4；321853-52-5
• 化学式: C₂₀H₂₃NO₄
• 分子量: 341.407
• InChiKey: YELSJKOYVBXPDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  (+)-2-[4-[[(3,5-dimethylanilino)carbonyl]methyl]phenoxy]-butanoic Acid 在 辛可尼丁 、 盐酸 作用下， 以 乙醇 、 甲醇 为溶剂， 生成 (+)-2-[4-[[(3,5-dimethylanilino)carbonyl]methyl]phenoxy]butanoic acid 、 (-)-2-[4-[[(3,5-dimethylanilino)carbonyl]methyl]phenoxy]butanoic 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
• 作为产物：
  描述：

  1-氨基-3,5-二甲苯 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 72.0h， 生成 (+)-2-[4-[[(3,5-dimethylanilino)carbonyl]methyl]phenoxy]-butanoic 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：Abraham J. Donald

  公开号：US20050154062A1

  公开（公告）日：2005-07-14

  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，通过降低全血中血红蛋白的氧亲和力，有助于向低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
• Compositions of Allosteric Hemoglobin Modifiers and Methods of Making the Same
  申请人：Quick Al

  公开号：US20070293698A1

  公开（公告）日：2007-12-20

  The present invention provides novel compositions of allosteric hemoglobin modifiers which are substantially free of impurities, specifically polymeric impurities. In one embodiment, the novel compositions contain an allosteric hemoglobin modifier compound and less than 100 ppm of the polymeric impurities generated during the preparation of this compound. Included in the present invention are novel methods for preparing allosteric hemoglobin modifiers that are substantially free of polymeric impurities. Also included in the present invention are improved methods for the purification of the product formed by the method of this invention. The novel methods of purification comprise extracting the crude composition with a water immiscible or partially immiscible solvent such as methylisobutyl ketone (MIBK) to lower amounts of impurities, specifically polymeric impurities. Also included are methods to reduce impurities by recrystallization of the crude synthesized product, followed by filtration of the recrystallized product. The present invention also includes the products made by the processes of the invention and methods for analyzing compositions comprised of these products.
• US6486342B1
  申请人：——

  公开号：US6486342B1

  公开（公告）日：2002-11-26