diethyl 2-(naphthalene-2-carbonylamino)propanedioate | 1072856-67-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: diethyl 2-(naphthalene-2-carbonylamino)propanedioate
• CAS: 1072856-67-7
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: MBOSKVSUZVVBHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  diethyl 2-(naphthalene-2-carbonylamino)propanedioate 在 三氟乙酸酐 作用下， 以 2,3,4-三氟甲苯 为溶剂， 生成
  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
• 作为产物：
  描述：

  氨基丙二酸二乙酯 、 2-萘甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 diethyl 2-(naphthalene-2-carbonylamino)propanedioate
  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