N⁴-(3-allyl-2-methyl-3H-benzimidazol-5-yl)-N²-(3-allyl-2-methyl-3H-benzimidazol-5-yl)quinazolin-2,4-diamine | 1537866-80-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N⁴-(3-allyl-2-methyl-3H-benzimidazol-5-yl)-N²-(3-allyl-2-methyl-3H-benzimidazol-5-yl)quinazolin-2,4-diamine
• 英文别名: 2-N,4-N-bis(2-methyl-3-prop-2-enylbenzimidazol-5-yl)quinazoline-2,4-diamine
• CAS: 1537866-80-0
• 化学式: C₃₀H₂₈N₈
• 分子量: 500.606
• InChiKey: MGNSXLDUCHFULH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  85.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,4-喹唑啉二酮 在 三乙胺 、 三氯氧磷 作用下， 以 异丙醇 为溶剂， 反应 7.0h， 生成 N⁴-(3-allyl-2-methyl-3H-benzimidazol-5-yl)-N²-(3-allyl-2-methyl-3H-benzimidazol-5-yl)quinazolin-2,4-diamine
  参考文献：
  名称：

  Synthesis and in vitro antitumor evaluation of primary amine substituted quinazoline linked benzimidazole

  摘要：

  By combining the structural features of quinazoline and benzimidazole, new hybrid regioisomeric molecules with substituted primary amines have been synthesized. Evaluation of these molecules over 60 cancer cell line panel has identified three molecules as most potent anticancer agents. Compound 10 showed ten and eleven folds more activity than respective quinazoline and benzimidazole class of compounds with GI(50) value of 1.64 mu M. Compound 11 (GI(50) value of 0.81 mu M) showed almost twenty and twenty-two fold more activity than quinazoline and benzimidazole analogue, respectively while compound 12 (GI(50) value of 4.52 mu M) has four fold more activity than quinazoline and benzimidazole analogue. In vitro evaluation of compound 11 exhibited remarkable anticancer activity towards colon cancer cell lines and prostate cancer cell lines at five dose concentrations with GI(50) values of 0.34 and 0.31 mu M, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.005

文献信息

• Synthesis and in vitro antitumor evaluation of primary amine substituted quinazoline linked benzimidazole
  作者：Kamaldeep Paul、Alka Sharma、Vijay Luxami

  DOI：10.1016/j.bmcl.2013.12.005

  日期：2014.1

  By combining the structural features of quinazoline and benzimidazole, new hybrid regioisomeric molecules with substituted primary amines have been synthesized. Evaluation of these molecules over 60 cancer cell line panel has identified three molecules as most potent anticancer agents. Compound 10 showed ten and eleven folds more activity than respective quinazoline and benzimidazole class of compounds with GI(50) value of 1.64 mu M. Compound 11 (GI(50) value of 0.81 mu M) showed almost twenty and twenty-two fold more activity than quinazoline and benzimidazole analogue, respectively while compound 12 (GI(50) value of 4.52 mu M) has four fold more activity than quinazoline and benzimidazole analogue. In vitro evaluation of compound 11 exhibited remarkable anticancer activity towards colon cancer cell lines and prostate cancer cell lines at five dose concentrations with GI(50) values of 0.34 and 0.31 mu M, respectively. (C) 2013 Elsevier Ltd. All rights reserved.