N-(4-氯苄基)-5-羟基-4-氧代-4H-苯并吡喃-2-甲酰胺 | 546093-13-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: N-(4-氯苄基)-5-羟基-4-氧代-4H-苯并吡喃-2-甲酰胺
• 英文名称: N-[(4-chlorophenyl)methyl]-5-hydroxy-4-oxochromene-2-carboxamide
• 英文别名: 5-Hydroxy-4-oxo-4H-chromene-2-carboxylic acid 4-chloro-benzylamide
• CAS: 546093-13-4
• 化学式: C₁₇H₁₂ClNO₄
• 分子量: 329.74
• InChiKey: WGJKPSDANGKFMV-UHFFFAOYSA-N

物化性质

• 沸点：
  582.1±50.0 °C(Predicted)
• 密度：
  1.457±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为产物：
  描述：

  2,6-二羟基苯乙酮 在 氢溴酸 、 sodium ethanolate 、 碳酸氢钠 、 potassium carbonate 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 44.0h， 生成 N-(4-氯苄基)-5-羟基-4-氧代-4H-苯并吡喃-2-甲酰胺
  参考文献：
  名称：

  Modulation of P-Glycoprotein-Mediated Multidrug Resistance by Flavonoid Derivatives and Analogues

  摘要：

  Flavonoid derivatives were synthesized and tested for their ability to modulate P-glycoprotein (Pgp)-mediated multidrug resistance (MDR) in vitro. These compounds belong to various flavonoid subclasses, namely: chromones, azaisoflavones, and aurones. Among the investigated compounds, three showed potent reversing activity. 2-(4-Methylpiperazin-1-ylcarbonyl)-5-hydroxychromone (4a), 5,7-dimethoxy-3-phenyl-4-quinolone (5), and 4,6-dimethoxyaurone (6) potentiated daunorubicin cytotoxicity on resistant K562 cells. They were also able to increase the intracellular accumulation of rhodamine-123, a fluorescent molecule which acts as a probe of P-glycoprotein-mediated MDR. This suggests that these compounds act, at least in part, by inhibiting P-glycoprotein activity. The most active compound, 5-hydroxy-2-(4-methylpiperazin-1-ylcarbonyl)chromone (4a) was found to be a powerful reversal agent, more potent than cyclosporin A, used as the reference molecule. No effect was observed on MRP transport nor on cell proliferation. Little apoptosis was induced on K562S cells with 4a compared to K562R, probably due to the extrusion of the compound by Pgp.

  DOI：

  10.1021/jm021099i

文献信息

• [EN] ANTI-INFECTIVE AGENTS<br/>[FR] AGENTS ANTI-INFECTIEUX
  申请人：UNIV DUNDEE

  公开号：WO2017221002A1

  公开（公告）日：2017-12-28

  The present invention relates to a novel class of chromene-2-carboxamide compounds inhibitors of general formula (I) wherein R1, R2, R3, R4, R5, R6, R7, R8 and X are as defined herein, to their use in medicine, and their use as anti-infective agents in particular, to compositions containing them, to processes for their preparation and to intermediates used in such processes.

  本发明涉及一类新型的基于色酮-2-羧酰胺化合物的抑制剂，其通式为(I)，其中R1、R2、R3、R4、R5、R6、R7、R8和X如本文所定义，其在医学上的用途，特别是作为抗感染剂的用途，包括含有它们的组合物，其制备过程以及用于这些过程的中间体。
• ANTI-INFECTIVE AGENTS
  申请人：University Of Dundee

  公开号：EP3472141A1

  公开（公告）日：2019-04-24
• Modulation of P-Glycoprotein-Mediated Multidrug Resistance by Flavonoid Derivatives and Analogues
  作者：Mohamed Hadjeri、Magali Barbier、Xavier Ronot、Anne-Marie Mariotte、Ahcène Boumendjel、Jean Boutonnat

  DOI：10.1021/jm021099i

  日期：2003.5.1

  Flavonoid derivatives were synthesized and tested for their ability to modulate P-glycoprotein (Pgp)-mediated multidrug resistance (MDR) in vitro. These compounds belong to various flavonoid subclasses, namely: chromones, azaisoflavones, and aurones. Among the investigated compounds, three showed potent reversing activity. 2-(4-Methylpiperazin-1-ylcarbonyl)-5-hydroxychromone (4a), 5,7-dimethoxy-3-phenyl-4-quinolone (5), and 4,6-dimethoxyaurone (6) potentiated daunorubicin cytotoxicity on resistant K562 cells. They were also able to increase the intracellular accumulation of rhodamine-123, a fluorescent molecule which acts as a probe of P-glycoprotein-mediated MDR. This suggests that these compounds act, at least in part, by inhibiting P-glycoprotein activity. The most active compound, 5-hydroxy-2-(4-methylpiperazin-1-ylcarbonyl)chromone (4a) was found to be a powerful reversal agent, more potent than cyclosporin A, used as the reference molecule. No effect was observed on MRP transport nor on cell proliferation. Little apoptosis was induced on K562S cells with 4a compared to K562R, probably due to the extrusion of the compound by Pgp.