2-amino-5-[4-(4-trifluoromethylbenzylamino)-3-nitrophenyl]pyrimidine | 742700-90-9

• 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-amino-5-[4-(4-trifluoromethylbenzylamino)-3-nitrophenyl]pyrimidine
• 英文别名: 5-[3-Nitro-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]pyrimidin-2-amine
• CAS: 742700-90-9
• 化学式: C₁₈H₁₄F₃N₅O₂
• 分子量: 389.337
• InChiKey: LSWXVGXDXYYLPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-amino-5-[4-(4-trifluoromethylbenzylamino)-3-nitrophenyl]pyrimidine 在 sodium hydroxide 作用下， 以 乙二醇乙醚 为溶剂， 反应 5.0h， 以77%的产率得到5-(2-aminopyrimidin-5-yl)-2-(4-trifluoromethylphenyl)-1H-benzimidazole-3-oxide
  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+
• 作为产物：
  描述：

  5-(4-氯苯基)-2-嘧啶胺 在 硫酸 、 硝酸 作用下， 反应 7.0h， 生成 2-amino-5-[4-(4-trifluoromethylbenzylamino)-3-nitrophenyl]pyrimidine
  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.