2-Bromomethyl-8-nitro-benzo[c]chromen-6-one | 827623-20-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2-Bromomethyl-8-nitro-benzo[c]chromen-6-one
• 英文别名: 2-(bromomethyl)-8-nitrobenzo[c]chromen-6-one
• CAS: 827623-20-1
• 化学式: C₁₄H₈BrNO₄
• 分子量: 334.126
• InChiKey: XVVDAQKSNQYMJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Bromomethyl-8-nitro-benzo[c]chromen-6-one 在 铁粉 、 氯化铵 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以83%的产率得到8-Amino-2-bromomethyl-benzo[c]chromen-6-one
  参考文献：
  名称：

  New 2-bromomethyl-8-substituted-benzo[c]chromen-6-ones. Synthesis and biological properties

  摘要：

  New 2-bromomethyl-8-substituted-benzo[c]chromen-6-ones have been synthesized and their bioactive properties have been evaluated on different enzymatic models: serine proteases (trypsin and a-chymotrypsin), HIV aspartyl protease, nitric oxide synthase and a panel of protein kinases. These new derivatives can provide upon chemical or enzymatic attack, very reactive quinonimine methide intermediates, which could be utilized for the design of enzyme inhibitors. We found that some of these new derivatives exhibit modest inhibitory activities on the studied enzyme models, but it could be improved after structure optimization. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.018
• 作为产物：
  描述：

  5-醛基-2-甲氧基苯硼酸 在 1,1'-双(二苯基膦)二茂铁 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 dimethyl sulfide borane 、 potassium acetate 、 三溴化硼 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 2-Bromomethyl-8-nitro-benzo[c]chromen-6-one
  参考文献：
  名称：

  New 2-bromomethyl-8-substituted-benzo[c]chromen-6-ones. Synthesis and biological properties

  摘要：

  New 2-bromomethyl-8-substituted-benzo[c]chromen-6-ones have been synthesized and their bioactive properties have been evaluated on different enzymatic models: serine proteases (trypsin and a-chymotrypsin), HIV aspartyl protease, nitric oxide synthase and a panel of protein kinases. These new derivatives can provide upon chemical or enzymatic attack, very reactive quinonimine methide intermediates, which could be utilized for the design of enzyme inhibitors. We found that some of these new derivatives exhibit modest inhibitory activities on the studied enzyme models, but it could be improved after structure optimization. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.018

文献信息

• New 2-bromomethyl-8-substituted-benzo[c]chromen-6-ones. Synthesis and biological properties
  作者：Cédrik Garino、Frédéric Bihel、Nicolas Pietrancosta、Younes Laras、Gilles Quéléver、Irene Woo、Peter Klein、Jenny Bain、Jean-Luc Boucher、Jean-Louis Kraus

  DOI：10.1016/j.bmcl.2004.10.018

  日期：2005.1

  New 2-bromomethyl-8-substituted-benzo[c]chromen-6-ones have been synthesized and their bioactive properties have been evaluated on different enzymatic models: serine proteases (trypsin and a-chymotrypsin), HIV aspartyl protease, nitric oxide synthase and a panel of protein kinases. These new derivatives can provide upon chemical or enzymatic attack, very reactive quinonimine methide intermediates, which could be utilized for the design of enzyme inhibitors. We found that some of these new derivatives exhibit modest inhibitory activities on the studied enzyme models, but it could be improved after structure optimization. (C) 2004 Elsevier Ltd. All rights reserved.