methyl 2-(6-methylindazol-4,7-dion-3-yl)-N-ethylcarbamate | 1206718-70-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-(6-methylindazol-4,7-dion-3-yl)-N-ethylcarbamate
• 英文别名: methyl N-[2-(6-methyl-4,7-dioxo-2H-indazol-3-yl)ethyl]carbamate
• CAS: 1206718-70-8
• 化学式: C₁₂H₁₃N₃O₄
• 分子量: 263.253
• InChiKey: LTOUTZOZVKZEER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(N-carbomethoxyamino)-1-diazopropane 、 甲基苯醌 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.5h， 生成 methyl 2-(6-methylindazol-4,7-dion-3-yl)-N-ethylcarbamate
  参考文献：
  名称：

  Synthesis of 3-[(N-carboalkoxy)ethylamino]-indazole-dione derivatives and their biological activities on human liver carbonyl reductase

  摘要：

  A series of indazole-dione derivatives were synthesized by the 1,3-dipolar cycloaddition reaction of appropriate substituted benzoquinones or naphthoquinones and N-carboalkoxyamino diazopropane derivatives. These compounds were evaluated for their effects on human carbonyl reductase. Several of the analogs were found to serve as substrates for carbonyl reductase with a wide range of catalytic efficiencies, while four analogs display inhibitory activities with IC50 values ranging from 3-5 mu M. Two of the inhibitors were studied in greater detail and were found to be noncompetitive inhibitors against both NADPH and menadione with K-I values ranging between 2 and 11 mu M. Computational studies suggest that conformation of the compounds may determine whether the indazole-diones bind productively to yield product or nonproductively to inhibit the enzyme. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.011

文献信息

• Synthesis of 3-[(N-carboalkoxy)ethylamino]-indazole-dione derivatives and their biological activities on human liver carbonyl reductase
  作者：Solomon Berhe、Andrew Slupe、Choice Luster、Henry A. Charlier、Don L. Warner、Leon H. Zalkow、Edward M. Burgess、Nkechi M. Enwerem、Oladapo Bakare

  DOI：10.1016/j.bmc.2009.11.011

  日期：2010.1

  A series of indazole-dione derivatives were synthesized by the 1,3-dipolar cycloaddition reaction of appropriate substituted benzoquinones or naphthoquinones and N-carboalkoxyamino diazopropane derivatives. These compounds were evaluated for their effects on human carbonyl reductase. Several of the analogs were found to serve as substrates for carbonyl reductase with a wide range of catalytic efficiencies, while four analogs display inhibitory activities with IC50 values ranging from 3-5 mu M. Two of the inhibitors were studied in greater detail and were found to be noncompetitive inhibitors against both NADPH and menadione with K-I values ranging between 2 and 11 mu M. Computational studies suggest that conformation of the compounds may determine whether the indazole-diones bind productively to yield product or nonproductively to inhibit the enzyme. (C) 2009 Elsevier Ltd. All rights reserved.