2-phthalimidopropiono-2',6'-xylidide | 71344-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-phthalimidopropiono-2',6'-xylidide
• 英文别名: N-(2,6-dimethylphenyl)-2-(1,3-dioxoisoindol-2-yl)propanamide
• CAS: 71344-61-1
• 化学式: C₁₉H₁₈N₂O₃
• 分子量: 322.364
• InChiKey: GYUXCUIFCZNCRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phthalimidopropiono-2',6'-xylidide 在 盐酸 、 一水合肼 作用下， 生成 邻苯二甲酰肼 、 妥卡尼
  参考文献：
  名称：

  New antiarrhythmic agents. 6. Quantitative structure-activity relationships of aminoxylidides

  摘要：

  The synthesis and pharmacological evaluation of primary and tertiary aminoxylidides with the amino group in the 2-7 position of the acyl chain are described. 2,6-Xylidine was acylated with haloacyl halides and converted to the target compounds by direct amination or by the Gabriel procedure. Alternatively, 2,6-xylidine was coupled with keto acids, and the ketoxylidides were converted to the amines by reductive amination. The target compounds were evaluated in mice both for antiarrhythmic efficacy against chloroform-induced tachycardia and for central nervous system toxicity. Experimentally determined values of partition coefficients and pKa values were used for quantitative structure-activity analyses. While the antiarrhythmic activity could be described as a function of log P alone, the CNS toxicity was best described as a function of both log P and pKa. The results suggest that antiarrhythmic potency can be increased by increasing lipophilicity, while the therapeutic index can be improved by increasing the pKa.

  DOI：

  10.1021/jm00139a007
• 作为产物：
  描述：

  potassium phtalimide 以90%的产率得到
  参考文献：
  名称：

  MCMASTER P. D.; BYRNES E. W.; FELDMAN H. S.; TAKMAN B. H.; TENTHOREY P. A+, J. MED. CHEM., 1979, 22, NO 10, 1177-1182

  摘要：

  DOI：

文献信息

• TENTHOREY, P. A.;BLOCK, A. J.;RONFELD, R. A.;MCMASTER, P. D.;BYRNES, E. W+, J. MED. CHEM., 1981, 24, N 7, 798-806
  作者：TENTHOREY, P. A.、BLOCK, A. J.、RONFELD, R. A.、MCMASTER, P. D.、BYRNES, E. W+

  DOI：——

  日期：——
• New antiarrhythmic agents. 6. Quantitative structure-activity relationships of aminoxylidides
  作者：Paul A. Tenthorey、Alan J. Block、Robert A. Ronfeld、Paul D. McMaster、Eugene W. Byrnes

  DOI：10.1021/jm00139a007

  日期：1981.7

  The synthesis and pharmacological evaluation of primary and tertiary aminoxylidides with the amino group in the 2-7 position of the acyl chain are described. 2,6-Xylidine was acylated with haloacyl halides and converted to the target compounds by direct amination or by the Gabriel procedure. Alternatively, 2,6-xylidine was coupled with keto acids, and the ketoxylidides were converted to the amines by reductive amination. The target compounds were evaluated in mice both for antiarrhythmic efficacy against chloroform-induced tachycardia and for central nervous system toxicity. Experimentally determined values of partition coefficients and pKa values were used for quantitative structure-activity analyses. While the antiarrhythmic activity could be described as a function of log P alone, the CNS toxicity was best described as a function of both log P and pKa. The results suggest that antiarrhythmic potency can be increased by increasing lipophilicity, while the therapeutic index can be improved by increasing the pKa.
• MCMASTER P. D.; BYRNES E. W.; FELDMAN H. S.; TAKMAN B. H.; TENTHOREY P. A+, J. MED. CHEM., 1979, 22, NO 10, 1177-1182
  作者：MCMASTER P. D.、 BYRNES E. W.、 FELDMAN H. S.、 TAKMAN B. H.、 TENTHOREY P. A+

  DOI：——

  日期：——