6-氯-N-(喹啉-8-基)烟酰胺 | 1016683-71-8

• 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
• 中文名称: 6-氯-N-(喹啉-8-基)烟酰胺
• 英文名称: 6-chloro-N-(quinolin-8-yl)nicotinamide
• 英文别名: 6-chloro-N-quinolin-8-ylpyridine-3-carboxamide
• CAS: 1016683-71-8
• 化学式: C₁₅H₁₀ClN₃O
• 分子量: 283.717
• InChiKey: BNPRJWOKEVYJIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-氯-N-(喹啉-8-基)烟酰胺 在 copper(l) iodide 、 碘苯二乙酸 、 氨基磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以73%的产率得到
  参考文献：
  名称：

  在温和条件下使用卤化铜对喹啉进行 PhI（OAc）2氧化C5卤化†

  摘要：

  开发了一种简洁有效的方案，用于在C5位置对喹啉进行PhI（OAc）2氧化卤化，以中等至极好的收率提供了所需的远程C–H活化产物。该反应用卤化铜作为卤化试剂进行，以提供卤化喹啉，并且具有优异的底物耐受性，为喹啉的C5卤化提供了简便的途径。

  DOI：

  10.1039/c6ra14863h
• 作为产物：
  描述：

  8-氨基喹啉 、 6-氯烟酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以67%的产率得到6-氯-N-(喹啉-8-基)烟酰胺
  参考文献：
  名称：

  Design, synthesis and biological evaluation of quinoline amide derivatives as novel VEGFR-2 inhibitors

  摘要：

  Vascular endothelial growth factor receptor-2 (VEGFR-2) plays a crucial role in the process of cancer angiogenesis. A series of quinoline amide derivatives were prepared and found to be good inhibitors of VEGFR-2. The inhibitory activities were investigated against VEGFR-2 kinase and human umbilical vein endothelial cells (HUVEC) in vitro. Compound 6 (5-chloro-2-hydroxy-N-(quinolin-8-yl)benzamide) exhibited the most potent inhibitory activity (IC(50) = 3.8 and 5.5 nM for VEGFR-2 kinase and HUVEC, respectively). Docking simulation supported the initial pharmacophoric hypothesis and suggested a common mode of interaction at the ATP-binding site of VEGFR-2, which demonstrates that compound 6 is a potential agent for cancer therapy deserving further researching. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.014

文献信息

• Nickel-catalyzed regioselective hydrogen isotope exchange accelerated by 2-pyridones
  作者：Zhi-Jiang Jiang、Si-Han Xu、Yuhang Su、Erxun Hu、Jiawei Han、Jian-Fei Bai、Bencan Tang、Jia Chen、Zhanghua Gao

  DOI：10.1039/d3cc05257e

  日期：——

  A nickel-catalyzed hydrogen isotope exchange has been developed with acetone-d6 as the deuterium source. The reaction showed an improved kinetic feature of H/D exchange under the assistance of 2-pyridones, efficiently affording regioselective labeled aryl and alkyl carboxamides.

  已开发出以丙酮-d 6作为氘源的镍催化氢同位素交换。该反应在 2-吡啶酮的帮助下表现出改进的 H/D 交换动力学特征，有效地提供区域选择性标记的芳基和烷基羧酰胺。
• PhI(OAc)₂ oxidative C5 halogenation of quinolines using copper halides under mild conditions
  作者：Xing-Xing Liu、Zhao-Yang Wu、Xin-Liang Luo、Yong-Qin He、Xiao-Qiang Zhou、Yu-Xing Fan、Guo-Sheng Huang

  DOI：10.1039/c6ra14863h

  日期：——

  protocol for PhI(OAc)2 oxidation halogenation of quinoline at the C5 position was developed, affording the desired remote C–H activation products in moderate to excellent yields. This reaction proceeds with copper halides as the halogenating reagent to afford the halogenated quinolines and features excellent substrate tolerance, providing a facile pathway for the C5 halogenation of quinoline.

  开发了一种简洁有效的方案，用于在C5位置对喹啉进行PhI（OAc）2氧化卤化，以中等至极好的收率提供了所需的远程C–H活化产物。该反应用卤化铜作为卤化试剂进行，以提供卤化喹啉，并且具有优异的底物耐受性，为喹啉的C5卤化提供了简便的途径。
• Design, synthesis and biological evaluation of quinoline amide derivatives as novel VEGFR-2 inhibitors
  作者：Ying Yang、Lei Shi、Yang Zhou、Huan-Qiu Li、Zhen-Wei Zhu、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2010.09.014

  日期：2010.11

  Vascular endothelial growth factor receptor-2 (VEGFR-2) plays a crucial role in the process of cancer angiogenesis. A series of quinoline amide derivatives were prepared and found to be good inhibitors of VEGFR-2. The inhibitory activities were investigated against VEGFR-2 kinase and human umbilical vein endothelial cells (HUVEC) in vitro. Compound 6 (5-chloro-2-hydroxy-N-(quinolin-8-yl)benzamide) exhibited the most potent inhibitory activity (IC(50) = 3.8 and 5.5 nM for VEGFR-2 kinase and HUVEC, respectively). Docking simulation supported the initial pharmacophoric hypothesis and suggested a common mode of interaction at the ATP-binding site of VEGFR-2, which demonstrates that compound 6 is a potential agent for cancer therapy deserving further researching. (C) 2010 Elsevier Ltd. All rights reserved.