4-[[(3-chloro-5-methylanilino)carbonyl]methyl]phenol | 321853-32-1

• 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: 4-[[(3-chloro-5-methylanilino)carbonyl]methyl]phenol
• 英文别名: N-(3-chloro-5-methylphenyl)-2-(4-hydroxyphenyl)acetamide
• CAS: 321853-32-1
• 化学式: C₁₅H₁₄ClNO₂
• 分子量: 275.735
• InChiKey: XSGCCWHHVTZCIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[[(3-chloro-5-methylanilino)carbonyl]methyl]phenol 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[4-[2-(3-Chloro-5-methylanilino)-2-oxoethyl]phenoxy]propanoic 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：

  3-氯-5-硝基甲苯 在 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 tin(ll) chloride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 4-[[(3-chloro-5-methylanilino)carbonyl]methyl]phenol
  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
• 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