2,4-diamino-5-(4-ethoxyethyloxy-3-nitrophenyl)-6-ethylpyrimidine

• 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: 2,4-diamino-5-(4-ethoxyethyloxy-3-nitrophenyl)-6-ethylpyrimidine
• 英文别名: 5-[4-(2-Ethoxyethoxy)-3-nitrophenyl]-6-ethylpyrimidine-2,4-diamine
• 化学式: C₁₆H₂₁N₅O₄
• 分子量: 347.374
• InChiKey: PSABSOUJQCPVDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  乙二醇乙醚 、 2,4-二氨基-5-(3-氨基-4-氯-5-硝基苯基)-6-乙基嘧啶 在 potassium carbonate 作用下， 反应 42.0h， 以62.5%的产率得到2,4-diamino-5-(4-ethoxyethyloxy-3-nitrophenyl)-6-ethylpyrimidine
  参考文献：
  名称：

  Structural Studies on Bioactive Compounds. 39. Biological Consequences of the Structural Modification of DHFR-Inhibitory 2,4-Diamino-6-(4-substituted benzylamino-3-nitrophenyl)-6-ethylpyrimidines (‘benzoprims')

  摘要：

  Benzimidazole-N-oxide modifications of potent lipophilic dihydrofolate reductase (DHFR) inhibitors (e.g., methylbenzoprim 1 and dichlorobenzoprim 2) have been prepared by basepromoted cyclization of the nitrophenylbenzylamino groups to explore the possibility that abrogation of DHFR-inhibitory activity might reveal clues to an alternative anti-ras mechanism. Examples of the new series had only low growth inhibitory activities (Gi(50) generally > 50 muM) against colon HCT116 and lung HT29 cell lines but, unlike methylbenzoprim, this activity was unaffected by hypoxanthine/thymidine rescue.

  DOI：

  10.1021/jm040785+

文献信息

• Structural Studies on Bioactive Compounds. 39. Biological Consequences of the Structural Modification of DHFR-Inhibitory 2,4-Diamino-6-(4-substituted benzylamino-3-nitrophenyl)-6-ethylpyrimidines (‘benzoprims')
  作者：Marianne L. Richardson、Karen A. Croughton、Charles S. Matthews、Malcolm F. G. Stevens

  DOI：10.1021/jm040785+

  日期：2004.7.1

  Benzimidazole-N-oxide modifications of potent lipophilic dihydrofolate reductase (DHFR) inhibitors (e.g., methylbenzoprim 1 and dichlorobenzoprim 2) have been prepared by basepromoted cyclization of the nitrophenylbenzylamino groups to explore the possibility that abrogation of DHFR-inhibitory activity might reveal clues to an alternative anti-ras mechanism. Examples of the new series had only low growth inhibitory activities (Gi(50) generally > 50 muM) against colon HCT116 and lung HT29 cell lines but, unlike methylbenzoprim, this activity was unaffected by hypoxanthine/thymidine rescue.