1-(3-methoxyphenylcarbamoyl)-1H-indazole-3-carboxylic acid ethyl ester | 1325682-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3-methoxyphenylcarbamoyl)-1H-indazole-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 1-[(3-methoxyphenyl)carbamoyl]indazole-3-carboxylate
• CAS: 1325682-78-7
• 化学式: C₁₈H₁₇N₃O₄
• 分子量: 339.351
• InChiKey: IQWUGNZHLFRZLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-甲氧基苯异氰酸 、 吲唑-3-羧酸乙脂 以 四氢呋喃 为溶剂， 反应 6.0h， 以74%的产率得到1-(3-methoxyphenylcarbamoyl)-1H-indazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Design, synthesis and evaluation of N-benzoylindazole derivatives and analogues as inhibitors of human neutrophil elastase

  摘要：

  Human neutrophil elastase (HNE) plays an important role in tumour invasion and inflammation. A series of N-benzoylindazoles was synthesized and evaluated for their ability to inhibit HNE. We found that this scaffold is appropriate for HNE inhibitors and that the benzoyl fragment at position 1 is essential for activity. The most active compounds inhibited HNE activity with IC50 values in the submicromolar range. Furthermore, docking studies indicated that the geometry of an inhibitor within the binding site and energetics of Michaelis complex formation were key factors influencing the inhibitor's biological activity. Thus, N-benzoylindazole derivatives and their analogs represent novel structural templates that can be utilized for further development of efficacious HNE inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.036

文献信息

• Design, synthesis and evaluation of N-benzoylindazole derivatives and analogues as inhibitors of human neutrophil elastase
  作者：Letizia Crocetti、Maria Paola Giovannoni、Igor A. Schepetkin、Mark T. Quinn、Andrei I. Khlebnikov、Agostino Cilibrizzi、Vittorio Dal Piaz、Alessia Graziano、Claudia Vergelli

  DOI：10.1016/j.bmc.2011.06.036

  日期：2011.8

  Human neutrophil elastase (HNE) plays an important role in tumour invasion and inflammation. A series of N-benzoylindazoles was synthesized and evaluated for their ability to inhibit HNE. We found that this scaffold is appropriate for HNE inhibitors and that the benzoyl fragment at position 1 is essential for activity. The most active compounds inhibited HNE activity with IC50 values in the submicromolar range. Furthermore, docking studies indicated that the geometry of an inhibitor within the binding site and energetics of Michaelis complex formation were key factors influencing the inhibitor's biological activity. Thus, N-benzoylindazole derivatives and their analogs represent novel structural templates that can be utilized for further development of efficacious HNE inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.