N-(1-benzyl-2-methyl-1H-benzimidazol-5-yl)-N'-(4-fluorophenyl)-6-morpholin-4-yl-[1,3,5]triazine-2,4-diamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N-(1-benzyl-2-methyl-1H-benzimidazol-5-yl)-N'-(4-fluorophenyl)-6-morpholin-4-yl-[1,3,5]triazine-2,4-diamine
• 英文别名: 2-N-(1-benzyl-2-methylbenzimidazol-5-yl)-4-N-(4-fluorophenyl)-6-morpholin-4-yl-1,3,5-triazine-2,4-diamine
• 化学式: C₂₈H₂₇FN₈O
• 分子量: 510.574
• InChiKey: ZHMACUZQGCCXKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  93
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-甲基-5-硝基苯并咪唑 在 碳酸氢钠 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 为溶剂， 反应 33.0h， 生成 N-(1-benzyl-2-methyl-1H-benzimidazol-5-yl)-N'-(4-fluorophenyl)-6-morpholin-4-yl-[1,3,5]triazine-2,4-diamine
  参考文献：
  名称：

  Triazine–benzimidazole hybrids: Anticancer activity, DNA interaction and dihydrofolate reductase inhibitors

  摘要：

  A new series of triazine-benzimidazole hybrids has been synthesized with different substitution of primary and secondary amines at one of the position of triazine in moderate to good yields. These compounds were evaluated for their inhibitory activities over 60 human tumor cell lines at one dose and five dose concentrations. Compounds 6b, 8 and 9 showed broad spectrum of antitumor activities with GI(50) values of 9.79, 2.58 and 3.81 mu M, respectively. DNA binding studies also indicated strong interaction properties of these compounds. These synthesized compounds also showed inhibition of mammalian dihydrofolate reductase (DHFR). Compound 6b was depicted as the most active member of DHFR inhibitor with IC50 value of 1.05 mu M. Molecular modelling studies were used to identify the stabilized interactions of Compound 6b within the active site of enzyme for DHFR. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.03.012

文献信息

• Triazine–benzimidazole hybrids: Anticancer activity, DNA interaction and dihydrofolate reductase inhibitors
  作者：Prinka Singla、Vijay Luxami、Kamaldeep Paul

  DOI：10.1016/j.bmc.2015.03.012

  日期：2015.4

  A new series of triazine-benzimidazole hybrids has been synthesized with different substitution of primary and secondary amines at one of the position of triazine in moderate to good yields. These compounds were evaluated for their inhibitory activities over 60 human tumor cell lines at one dose and five dose concentrations. Compounds 6b, 8 and 9 showed broad spectrum of antitumor activities with GI(50) values of 9.79, 2.58 and 3.81 mu M, respectively. DNA binding studies also indicated strong interaction properties of these compounds. These synthesized compounds also showed inhibition of mammalian dihydrofolate reductase (DHFR). Compound 6b was depicted as the most active member of DHFR inhibitor with IC50 value of 1.05 mu M. Molecular modelling studies were used to identify the stabilized interactions of Compound 6b within the active site of enzyme for DHFR. (C) 2015 Elsevier Ltd. All rights reserved.