(E)-N1-[(2'-chloroquinolin-3'-yl)methylene]-4-phenyl-1H-imidazole-1,2-diamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-N1-[(2'-chloroquinolin-3'-yl)methylene]-4-phenyl-1H-imidazole-1,2-diamine
• 英文别名: 1-[(E)-(2-chloroquinolin-3-yl)methylideneamino]-4-phenylimidazol-2-amine
• 化学式: C₁₉H₁₄ClN₅
• 分子量: 347.807
• InChiKey: MOOOJLBPGKKJDV-SSDVNMTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯-3-喹啉甲醛 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 (E)-N1-[(2'-chloroquinolin-3'-yl)methylene]-4-phenyl-1H-imidazole-1,2-diamine
  参考文献：
  名称：

  Design, regioselective synthesis and cytotoxic evaluation of 2-aminoimidazole–quinoline hybrids against cancer and primary endothelial cells

  摘要：

  In search of new selective anti-cancer agents, a series of sixteen novel 2-aminoimidazole quinoline hybrid compounds (5a-5p) have been designed and synthesized regioselectively. We have characterized the compounds extensively using IR, 1D and 2D NMR Spectroscopy and mass spectrometry. The cytotoxicity studies against different cancer cell lines showed that the compound 5a (Imd-Ph) emerged as a potent cytotoxic scaffold. Imd-Ph (5a) exhibited a selective anticancer activity against human colon cancer cell line (HCT-116, DLD-1) and was found relatively non-toxic to breast cancer cells (MDA-MB-231) as well as to normal primary endothelial cells (HUVEC). Structure-activity relationship of imidazole -quinoline hybrid scaffolds revealed differential and selective toxicities exerted by the different derivatives against cancer and normal cells. Structural modification of the scaffold with library of a wide variety of substituents may lead to the development of novel selective anti-cancer agents in the future. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.055

文献信息

• Design, regioselective synthesis and cytotoxic evaluation of 2-aminoimidazole–quinoline hybrids against cancer and primary endothelial cells
  作者：Kuldeep Singh、Vikas Verma、Kavita Yadav、Vedagopuram Sreekanth、Devinder Kumar、Avinash Bajaj、Vinod Kumar

  DOI：10.1016/j.ejmech.2014.09.055

  日期：2014.11

  In search of new selective anti-cancer agents, a series of sixteen novel 2-aminoimidazole quinoline hybrid compounds (5a-5p) have been designed and synthesized regioselectively. We have characterized the compounds extensively using IR, 1D and 2D NMR Spectroscopy and mass spectrometry. The cytotoxicity studies against different cancer cell lines showed that the compound 5a (Imd-Ph) emerged as a potent cytotoxic scaffold. Imd-Ph (5a) exhibited a selective anticancer activity against human colon cancer cell line (HCT-116, DLD-1) and was found relatively non-toxic to breast cancer cells (MDA-MB-231) as well as to normal primary endothelial cells (HUVEC). Structure-activity relationship of imidazole -quinoline hybrid scaffolds revealed differential and selective toxicities exerted by the different derivatives against cancer and normal cells. Structural modification of the scaffold with library of a wide variety of substituents may lead to the development of novel selective anti-cancer agents in the future. (C) 2014 Elsevier Masson SAS. All rights reserved.