2-(1,3-苯并二氧戊环-5-基)-6-氟-3-羟基-4H-苯并吡喃-4-酮 | 4257-54-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 2-(1,3-苯并二氧戊环-5-基)-6-氟-3-羟基-4H-苯并吡喃-4-酮
• 英文名称: 2-(benzo[d][1,3]dioxol-5-yl)-6-fluoro-3-hydroxy-4H-chromen-4-one
• 英文别名: 6-Fluor-3'.4'-methylendioxy-flavonol；2-benzo[1,3]dioxol-5-yl-6-fluoro-3-hydroxy-chromen-4-one；2-(1,3-Benzodioxol-5-yl-6-Fluoro-3-Hydroxy-4H-Chromen-4-One；2-(1,3-benzodioxol-5-yl)-6-fluoro-3-hydroxychromen-4-one
• CAS: 4257-54-9
• 化学式: C₁₆H₉FO₅
• 分子量: 300.243
• InChiKey: HOOKBINPTRTSKO-UHFFFAOYSA-N

物化性质

• 熔点：
  116 °C
• 沸点：
  462.2±45.0 °C(Predicted)
• 密度：
  1.583±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(Benzo[1,3]dioxol-5-yl)-1-(5-fluoro-2-hydroxyphenyl)-2-propen-1-one 在 双氧水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以52%的产率得到2-(1,3-苯并二氧戊环-5-基)-6-氟-3-羟基-4H-苯并吡喃-4-酮
  参考文献：
  名称：

  SAR Studies and Biological Characterization of a Chromen-4-one Derivative as an Anti-Trypanosoma brucei Agent

  摘要：

  Chemical modulation of the flavonol 2-(benzo[d] [1,3]dioxo1-5-y1)-chromen-4-one (1), a promising anti-Trypanosomatid agent previously identified, was evaluated through a phenotypic screening approach. Herein, we have performed structure activity relationship studies around hit compound 1. The pivaloyl derivative (13) showed significant anti-T. brucei activity (EC50 = 1.1 1iM) together with a selectivity index higher than 92. The early in vitro ADME-tox properties (cytotoxicity, mitochondria] toxicity, cytochrome P450 and hERG inhibition) were determined for compound 1 and its derivatives, and these led to the identification of some liabilities. The 1,3-benzodioxole moiety in the presented compounds confers better in vivo pharmacokinetic properties than those of classical flavonols. Further studies using different delivery systems could lead to an increase of compound blood levels.

  DOI：

  10.1021/acsmedchemlett.8b00565

文献信息

• NOVEL CDK INHIBITORS HAVING FLAVONE STRUCTURE
  申请人：LG CHEMICAL LIMITED

  公开号：EP1109800A1

  公开（公告）日：2001-06-27
• US6500846B1
  申请人：——

  公开号：US6500846B1

  公开（公告）日：2002-12-31
• [EN] NOVEL CDK INHIBITORS HAVING FLAVONE STRUCTURE<br/>[FR] NOUVEAUX INHIBITEURS DE KINASE DEPENDANTE DES CYCLINES (CDK) PRESENTANT UNE STRUCTURE FLAVONE
  申请人：LG CHEMICAL LTD

  公开号：WO2000012496A1

  公开（公告）日：2000-03-09

  The present invention relates to a novel flavone derivative, pharmaceutically acceptable salt, hydrate, solvate and isomer thereof which is useful as an inhibitor against Cyclin Dependent Kinase (CDK), a process for preparation thereof, and a composition of anti-cancer agent or agent for treating neurodegenerative disease comprising this compound as an active ingredient.