2-Oxo-1,2-dihydroquinolin-4-yl furan-2-carboxylate | 1174986-46-9

• 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: 2-Oxo-1,2-dihydroquinolin-4-yl furan-2-carboxylate
• 英文别名: (2-oxo-1H-quinolin-4-yl) furan-2-carboxylate
• CAS: 1174986-46-9
• 化学式: C₁₄H₉NO₄
• 分子量: 255.23
• InChiKey: DBLROCQCWNGYTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  呋喃甲酰氯 、 2,4-喹啉二醇 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 2-Oxo-1,2-dihydroquinolin-4-yl furan-2-carboxylate
  参考文献：
  名称：

  Structure–activity relationships of heteroaromatic esters as human rhinovirus 3C protease inhibitors

  摘要：

  Human rhinovirus 3C protease (HRV 3C(pro)) is known to be a promising target for development of therapeutic agents against the common cold because of the importance of the protease in viral replication as well as its expression in a large number of serotypes. To explore non-peptidic inhibitors of HRV 3C(pro), a series of novel heteroaromatic esters was synthesized and evaluated for inhibitory activity against HRV 3C(pro), to determine the structure-activity relationships. The most potent inhibitor, 7, with a 5-bromopyridinyl group, had an IC50 value of 80 nM. In addition, the binding mode of a novel analog, 19, with the 4-hydroxyquinolinone moiety, was explored by molecular docking, suggesting a new interaction in the S1 pocket. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.114

文献信息

• Structure–activity relationships of heteroaromatic esters as human rhinovirus 3C protease inhibitors
  作者：Isak Im、Eui Seung Lee、Soo Jeong Choi、Ju-Yeon Lee、Yong-Chul Kim

  DOI：10.1016/j.bmcl.2009.04.114

  日期：2009.7

  Human rhinovirus 3C protease (HRV 3C(pro)) is known to be a promising target for development of therapeutic agents against the common cold because of the importance of the protease in viral replication as well as its expression in a large number of serotypes. To explore non-peptidic inhibitors of HRV 3C(pro), a series of novel heteroaromatic esters was synthesized and evaluated for inhibitory activity against HRV 3C(pro), to determine the structure-activity relationships. The most potent inhibitor, 7, with a 5-bromopyridinyl group, had an IC50 value of 80 nM. In addition, the binding mode of a novel analog, 19, with the 4-hydroxyquinolinone moiety, was explored by molecular docking, suggesting a new interaction in the S1 pocket. (C) 2009 Elsevier Ltd. All rights reserved.