5-(4-chlorophenyl)-6-propylpyrimidine-2,4-diamine | 18588-54-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-(4-chlorophenyl)-6-propylpyrimidine-2,4-diamine
• 英文别名: 5-(4-chloro-phenyl)-6-propyl-pyrimidine-2,4-diamine；5-(4-chloro-phenyl)-6-propyl-pyrimidine-2,4-diyldiamine；5-(4-Chlor-phenyl)-6-propyl-pyrimidin-2,4-diyldiamin；2,4-diamino-5-(p-chlorophenyl)-6-n-propylpyrimidine；2,4-Diamino-5-(4-chlor-phenyl)-6-propyl-pyrimidin；Pyrimidine, 2,4-diamino-5-(p-chlorophenyl)-6-n-propyl-
• CAS: 18588-54-0
• 化学式: C₁₃H₁₅ClN₄
• 分子量: 262.742
• InChiKey: YEXIBPDKYUNGGR-UHFFFAOYSA-N

物化性质

• 熔点：
  171-174 °C
• 沸点：
  496.8±55.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对氯苯乙腈 在 乙醚 、 sodium ethanolate 作用下， 生成 5-(4-chlorophenyl)-6-propylpyrimidine-2,4-diamine
  参考文献：
  名称：

  2,4-Diaminopyrimidines as Antimalarials. III. 5-Aryl Derivatives

  摘要：

  DOI：

  10.1021/ja01152a060

文献信息

• COMPOUNDS FOR THE TREATMENT OF LYSOSOMAL STORAGE DISEASES
  申请人：MAHURAN Don

  公开号：US20110195985A1

  公开（公告）日：2011-08-11

  A method of treating a lysosomal storage disease comprises administering a pyrimethamine derivative to a subject in need thereof.

  一种治疗溶酶体贮积病的方法，包括向需要治疗的受试者给予嘧啶甲酰胺衍生物。
• Pyrimethamine Derivatives: Insight into Binding Mechanism and Improved Enhancement of Mutant β-<i>N</i>-acetylhexosaminidase Activity
  作者：Michael B. Tropak、Jianmin Zhang、Sayuri Yonekawa、Brigitte A. Rigat、Virender S. Aulakh、Matthew R. Smith、Hee-Jong Hwang、Marco A. Ciufolini、Don J. Mahuran

  DOI：10.1021/jm5017895

  日期：2015.6.11

  In order to identify structural features of pyrimethamine (5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine) that contribute to its inhibitory activity (IC50 value) and chaperoning efficacy toward beta-N-acetylhexosaminidase, derivatives of the compound were synthesized that differ at the positions bearing the amino, ethyl, and chloro groups. Whereas the amino groups proved to be critical to its inhibitory activity, a variety of substitutions at the chloro position only increased its IC50 by 2-3-fold. Replacing the ethyl group at the 6-position with butyl or methyl groups increased IC50 more than 10-fold. Surprisingly, despite its higher IC50, a derivative lacking the chlorine atom in the para-position was found to enhance enzyme activity in live patient cells a further 25% at concentrations >100 mu M, while showing less toxicity. These findings demonstrate the importance of the phenyl group in modulating the chaperoning efficacy and toxicity profile of the derivatives.
• US4094976A
  申请人：——

  公开号：US4094976A

  公开（公告）日：1978-06-13
• 2,4-Diaminopyrimidines as Antimalarials. III. 5-Aryl Derivatives
  作者：Peter B. Russell、George H. Hitchings

  DOI：10.1021/ja01152a060

  日期：1951.8