7-羟基-2-氧代-N-苯基-2H-1-苯并吡喃-3-甲酰胺 | 94108-86-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 7-羟基-2-氧代-N-苯基-2H-1-苯并吡喃-3-甲酰胺
• 英文名称: N-phenyl-7-hydroxy-2-oxo-2H-1-benzopyran-3-carboxamide
• 英文别名: 7-hydroxy-2-oxo-N-phenyl-2H-chromene-3-carboxamide；7-Hydroxy-2-oxo-N-phenyl-2H-1-benzopyran-3-carboxamide；7-hydroxy-2-oxo-N-phenylchromene-3-carboxamide
• CAS: 94108-86-8
• 化学式: C₁₆H₁₁NO₄
• 分子量: 281.268
• InChiKey: BSNFVFFEEGERCW-UHFFFAOYSA-N

物化性质

• 沸点：
  609.2±55.0 °C(Predicted)
• 密度：
  1.464±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2932209090

反应信息

• 作为产物：
  描述：

  7-羟基香豆素-3-羧酸乙酯 在 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 7-羟基-2-氧代-N-苯基-2H-1-苯并吡喃-3-甲酰胺
  参考文献：
  名称：

  香豆素-3-羧酰胺作为选择性碳酸酐酶IX和XII抑制剂的设计，合成和生物学评估。

  摘要：

  通过使7-羟基-2-氧代-2H-亚甲基-3-羧酸与各种取代的芳族胺反应，合成了一系列新型的7-羟基香豆素-3-羧酰胺。评价了新合成的化合物对四种生理相关的人碳酸酐酶（hCA，EC 4.2.1.1）同工型CA I，CA II，CA IX和CA XII的抑制活性。CA抑制结果表明，新合成的7-羟基香豆素-3-羧酰胺（4a-n）相对于CA I和II异构体对肿瘤相关同种型CA IX和CA XII表现出选择性抑制作用。抑制常数的范围从亚微摩尔到低微摩尔。在所有测试的化合物中，化合物4m是对hCA IX和hCA XII均表现出亚微摩尔效价的最有效抑制剂，Ki为0.2 µM。所以，可以预料，化合物4m通过表现出新的作用机理可以作为抗癌治疗发展的先导。通过对接研究研究了hCA IX和XII催化裂隙中最有效化合物的结合模式。

  DOI：

  10.1016/j.bioorg.2019.02.004

文献信息

• N-(Hydroxyalkyl)-7-hydroxycoumarin-3-carboxamides
  申请人：MILES LABORATORIES, INC.

  公开号：EP0037979A2

  公开（公告）日：1981-10-21

  Title compounds of the formula: wherein R is hydroxy substituted lower alkyl. The compounds have advantageous water solubility and spectral characteristics for use as instrument calibrators for certain homogeneous fluorescent immunoassays.

  式中的标题化合物： 其中 R 是羟基取代的低级烷基。这些化合物具有良好的水溶性和光谱特性，可用作某些均相荧光免疫分析的仪器校准物。
• Novel 3-Carboxamide-coumarins as Potent and Selective FXIIa Inhibitors
  作者：Séverine Robert、Carine Bertolla、Bernard Masereel、Jean-Michel Dogné、Lionel Pochet

  DOI：10.1021/jm8002697

  日期：2008.6.1

  Recently, FXIIa was highlighted as an original attractive target for the development of new anticoagulant drugs with low rates of therapy-related hemorrhages. In this work, we describe the development of a new series of 3-carboxamide-coumarins that are the first potent and selective nonpeptidic inhibitors of FXIIa.
• 7-Hydroxycoumarins Are Affinity-Based Fluorescent Probes for Competitive Binding Studies of Macrophage Migration Inhibitory Factor
  作者：Zhangping Xiao、Deng Chen、Shanshan Song、Ramon van der Vlag、Petra E. van der Wouden、Ronald van Merkerk、Robbert H. Cool、Anna K. H. Hirsch、Barbro N. Melgert、Wim J. Quax、Gerrit J. Poelarends、Frank J. Dekker

  DOI：10.1021/acs.jmedchem.0c01160

  日期：2020.10.22

  Macrophage migration inhibitory factor (MIF) is a cytokine with key roles in inflammation and cancer, which qualifies it as a potential drug target. Apart from its cytokine activity, MIF also harbors enzyme activity for keto-enol tautomerization. MIF enzymatic activity has been used for identification of MIF binding molecules that also interfere with its biological activity. However, MIF tautomerase activity assays are troubled by irregularities, thus creating a need for alternative methods. In this study, we identified a 7-hydroxycoumarin fluorophore with high affinity for the MIF tautomerase active site (Ki = 18 ± 1 nM) that binds with concomitant quenching of its fluorescence. This property enabled development of a novel competition-based assay format to quantify MIF binding. We also demonstrated that the 7-hydroxycoumarin fluorophore interfered with the MIF-CD74 interaction and inhibited proliferation of A549 cells. Thus, we provide a high-affinity MIF binder as a novel tool to advance MIF-oriented research.
• Pyrimidone derivatives, processes for their preparation and pharmaceutical compositions containing them
  申请人：SMITH KLINE & FRENCH LABORATORIES LIMITED

  公开号：EP0039989B1

  公开（公告）日：1984-08-29
• Multilayer analytical element; method for its preparation and its use in analytical methods
  申请人：MILES INC.

  公开号：EP0069281B1

  公开（公告）日：1985-09-25