N-[hexyl]-N-[2-(dimethylamino)ethyl]quinolin-2-amine | 1436382-40-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-[hexyl]-N-[2-(dimethylamino)ethyl]quinolin-2-amine
• 英文别名: N'-hexyl-N,N-dimethyl-N'-quinolin-2-ylethane-1,2-diamine
• CAS: 1436382-40-9
• 化学式: C₁₉H₂₉N₃
• 分子量: 299.459
• InChiKey: MSCWXYOKQOUSSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  19.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氯喹啉 在 lithium amide 作用下， 以 乙腈 为溶剂， 反应 20.08h， 生成 N-[hexyl]-N-[2-(dimethylamino)ethyl]quinolin-2-amine
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel FAK scaffold inhibitors targeting the FAK–VEGFR3 protein–protein interaction

  摘要：

  Focal adhesion kinase (FAK) and vascular endothelial growth factor receptor 3 (VEGFR3) are tyrosine kinases, which function as key modulators of survival and metastasis signals in cancer cells. Previously, we reported that small molecule chlorpyramine hydrochloride (C4) specifically targets the interaction between FAK and VEGFR3 and exhibits anti-tumor efficacy. In this study, we designed and synthesized a series of 1 (C4) analogs on the basis of structure activity relationship and molecular modeling. The resulting new compounds were evaluated for their binding to the FAT domain of FAK and anti-cancer activity. Amongst all tested analogs, compound 29 augmented anti-proliferative activity in multiple cancer cell lines with stronger binding to the FAT domain of FAK and disrupted the FAK-VEGFR3 interaction. In conclusion, we hope that this work will contribute to further studies of more potent and selective FAK-VEGFR3 protein-protein interaction inhibitors.

  DOI：

  10.1016/j.ejmech.2014.04.041

文献信息

• KINASE PROTEIN BINDING INHIBITORS
  申请人：ROSWELL PARK CANCER INSTITUTE

  公开号：US20150051245A1

  公开（公告）日：2015-02-19

  The invention relates to protein binding inhibitor compounds and methods of identifying and using them. The invention further relates to pharmaceutical compositions and methods for treating cell proliferative disorders, especially cancer.
• US9394253B2
  申请人：——

  公开号：US9394253B2

  公开（公告）日：2016-07-19
• Design, synthesis, and biological evaluation of novel FAK scaffold inhibitors targeting the FAK–VEGFR3 protein–protein interaction
  作者：Priyanka N. Gogate、Manivannan Ethirajan、Elena V. Kurenova、Andrew T. Magis、Ravindra K. Pandey、William G. Cance

  DOI：10.1016/j.ejmech.2014.04.041

  日期：2014.6

  Focal adhesion kinase (FAK) and vascular endothelial growth factor receptor 3 (VEGFR3) are tyrosine kinases, which function as key modulators of survival and metastasis signals in cancer cells. Previously, we reported that small molecule chlorpyramine hydrochloride (C4) specifically targets the interaction between FAK and VEGFR3 and exhibits anti-tumor efficacy. In this study, we designed and synthesized a series of 1 (C4) analogs on the basis of structure activity relationship and molecular modeling. The resulting new compounds were evaluated for their binding to the FAT domain of FAK and anti-cancer activity. Amongst all tested analogs, compound 29 augmented anti-proliferative activity in multiple cancer cell lines with stronger binding to the FAT domain of FAK and disrupted the FAK-VEGFR3 interaction. In conclusion, we hope that this work will contribute to further studies of more potent and selective FAK-VEGFR3 protein-protein interaction inhibitors.