2-hydroxymethyl-8-methoxy-3-(3-methoxy-4-methoxymethoxyphenyl)-2,3-dihydrobenzo[1,4]dioxine-6-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2-hydroxymethyl-8-methoxy-3-(3-methoxy-4-methoxymethoxyphenyl)-2,3-dihydrobenzo[1,4]dioxine-6-carbaldehyde
• 英文别名: 3-(Hydroxymethyl)-5-methoxy-2-[3-methoxy-4-(methoxymethoxy)phenyl]-2,3-dihydro-1,4-benzodioxine-7-carbaldehyde
• 化学式: C₂₀H₂₂O₈
• 分子量: 390.39
• InChiKey: QYFZRBAUVBCFBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  反式-3-(4-羟基-3-甲氧基苯基)-2-丙烯-1-醇 在 sodium hydride 、 silver carbonate 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 、 苯 为溶剂， 反应 8.0h， 生成 2-hydroxymethyl-8-methoxy-3-(3-methoxy-4-methoxymethoxyphenyl)-2,3-dihydrobenzo[1,4]dioxine-6-carbaldehyde
  参考文献：
  名称：

  Synthesis and Structures of Regioisomeric Hydnocarpin-Type Flavonolignans

  摘要：

  Flavonolignans represent natural compounds whose biosynthesis presumes a radical coupling of a ring B catecholic flavonoid with a molecule of coniferyl alcohol or an analogue. Many natural flavonolignans can exist as regioisomers, depending on how the coupled coniferyl alcohol moiety orients to the flavonoid. These regioisomers are often difficult to separate and have virtually identical NMR spectra. Structural assignments for some have changed with time or have been given without proof. We here report syntheses of both regioisomers of the flavonolignan hydnocarpin and one isomer of a plant isolate previously known as 5'-methoxyhydnocarpin. This isomer, here renamed 5'-methoxyhydnocarpin-D, was recently shown to be a potent inhibitor of a Staphylococcus aureus multidrug resistant efflux pump.

  DOI：

  10.1021/np000166d

文献信息

• [EN] MULTIDRUG RESISTANCE PUMP INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE POMPE A RESISTANCE MULTIPLE ET UTILISATIONS
  申请人：UNIV COLORADO STATE RES FOUND

  公开号：WO2001007034A1

  公开（公告）日：2001-02-01

  The present invention provides a method for determining the presence of a multidrug resistance (MDR) pump inhibitor in a natural antibiotic producing source, including plants and microorganisms, such as fungi and bacteria. The plant is selected from plants which produce amphiphilic cations such as isoquinolines, e.g., berberine and protoberberinium alkaloids. The present invention also provides flavolignans and porphyrin derivative compounds which have been identified by the method of the present invention as being MDR pump inhibitors.
• Synthesis and Structures of Regioisomeric Hydnocarpin-Type Flavonolignans
  作者：Nathan R. Guz、Frank R. Stermitz

  DOI：10.1021/np000166d

  日期：2000.8.1

  Flavonolignans represent natural compounds whose biosynthesis presumes a radical coupling of a ring B catecholic flavonoid with a molecule of coniferyl alcohol or an analogue. Many natural flavonolignans can exist as regioisomers, depending on how the coupled coniferyl alcohol moiety orients to the flavonoid. These regioisomers are often difficult to separate and have virtually identical NMR spectra. Structural assignments for some have changed with time or have been given without proof. We here report syntheses of both regioisomers of the flavonolignan hydnocarpin and one isomer of a plant isolate previously known as 5'-methoxyhydnocarpin. This isomer, here renamed 5'-methoxyhydnocarpin-D, was recently shown to be a potent inhibitor of a Staphylococcus aureus multidrug resistant efflux pump.