2-(4-羟基-3-甲氧基苯基)-7-甲氧基-5-苯并呋喃丙醇 | 144735-57-9

• 物质功能分类: 天然产物 - 木脂素
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 中文名称: 2-(4-羟基-3-甲氧基苯基)-7-甲氧基-5-苯并呋喃丙醇
• 英文名称: 2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxybenzofurane
• 英文别名: 4-(5-(3-hydroxypropyl)-7-methoxybenzofuran-2-yl)-2-methoxyphenol；4-O-demethylhomoegonol；4-[5-(3-hydroxypropyl)-7-methoxy-1-benzofuran-2-yl]-2-methoxyphenol
• CAS: 144735-57-9
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: FEONDVSBLGLFAZ-UHFFFAOYSA-N

物化性质

• 熔点：
  102-104 °C
• 沸点：
  516.6±45.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  72.1
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  2-(4-羟基-3-甲氧基苯基)-7-甲氧基-5-苯并呋喃丙醇 在 palladium on activated charcoal 吡啶 、 盐酸 、 ammonium hydroxide 、 sodium hydroxide 、 potassium chloride 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 35.17h， 生成 5-(3-hydroxypropyl)-7-methoxy-3-methyl-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran
  参考文献：
  名称：

  Compounds from Danshen. Part 7. Regioselective introduction of carbon-3 substituents to 5-alkyl-7-methoxy-2-phenylbenzo[b]furans: synthesis of a novel adenosine A1 receptor ligand and its derivatives

  摘要：

  By maintaining the balance between the electronic requirements, the stereochemical restrictions as well as the kinetic and thermodynamic factors, the unprecedented regioselective electrophilic aromatic substitution of formyl and nitro groups to carbon-3 of 5-alkyl-7-methoxy-2-phenylbenzo[b]furans have been achieved. Subsequent transformation of the resulting formyl group into methyl, hydroxymethyl, 1-hydroxyethyl, and cyano groups are also described.

  DOI：

  10.1021/jo00052a046
• 作为产物：
  描述：

  5-溴香兰素 在 palladium on activated charcoal 四氢吡咯 、 吡啶 、 ammonium hydroxide 、 lithium aluminium tetrahydride 、 盐酸羟胺 、 氢气 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 40.0h， 生成 2-(4-羟基-3-甲氧基苯基)-7-甲氧基-5-苯并呋喃丙醇
  参考文献：
  名称：

  Compounds from Danshen. Part 7. Regioselective introduction of carbon-3 substituents to 5-alkyl-7-methoxy-2-phenylbenzo[b]furans: synthesis of a novel adenosine A1 receptor ligand and its derivatives

  摘要：

  By maintaining the balance between the electronic requirements, the stereochemical restrictions as well as the kinetic and thermodynamic factors, the unprecedented regioselective electrophilic aromatic substitution of formyl and nitro groups to carbon-3 of 5-alkyl-7-methoxy-2-phenylbenzo[b]furans have been achieved. Subsequent transformation of the resulting formyl group into methyl, hydroxymethyl, 1-hydroxyethyl, and cyano groups are also described.

  DOI：

  10.1021/jo00052a046

文献信息

• An alternate method for the synthesis of 2-aryl/alkyl-5-bromo-7-methoxy benzofurans; application to the synthesis of Egonol, Homoegonol, and analogs via Heck reaction
  作者：Kishor R. More、R.S. Mali

  DOI：10.1016/j.tet.2016.09.068

  日期：2016.11

  We herein report the general, versatile, and convenient method for the synthesis of 2-arly/alkyl-5-bromo-7-methoxy benzofurans from easily available o-Vanillin in five steps. These benzofurans was successfully converted into biological active natural products Egonol, Homoegonol, and analogous on applying Heck reaction using ethyl/methyl acrylate in the presence of palladium catalyst.

  我们在此报告了在五个步骤中从容易获得的邻香兰素中合成2-芳基/烷基-5-溴-7-甲氧基苯并呋喃的通用，通用和方便的方法。这些苯并呋喃已成功转化为生物活性天然产物Egonol，Homoegonol，并且类似于在钯催化剂存在下使用乙基丙烯酸乙酯/丙烯酸甲酯进行的Heck反应。
• NOVEL 2-PHENYLBENZOFURAN DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, PRODUCTION METHOD FOR SAME AND PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING INFLAMMATORY DISEASE COMPRISING SAME AS ACTIVE INGREDIENT
  申请人：KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY

  公开号：US20160332980A1

  公开（公告）日：2016-11-17

  The present invention relates to a novel 2-phenylbenzofuran derivative or a pharmaceutically acceptable salt thereof, a production method for the same, and a pharmaceutical composition for preventing or treating an inflammatory disease comprising the same as an active ingredient, and the novel 2-phenylbenzofuran derivative or the pharmaceutically acceptable salt thereof according to the present invention is outstandingly effective in suppressing NO, IL-6, and TNF-alpha induced by macrophages, and therefore can advantageously be used in a pharmaceutical composition for preventing or treating an inflammatory disease.

  本发明涉及一种新的2-苯基苯并呋喃衍生物或其药学上可接受的盐，以及其制备方法，以及包含其作为活性成分的用于预防或治疗炎症性疾病的药物组合物，根据本发明的新的2-苯基苯并呋喃衍生物或其药学上可接受的盐在抑制由巨噬细胞诱导的NO、IL-6和TNF-alpha方面具有显著的有效性，因此可以有利地用于预防或治疗炎症性疾病的药物组合物中。
• Facile Preparation of 2-Arylbenzo[b]furan Molecules and Their Anti-inflammatory Effects
  作者：Jung-Woon Hwang、Da-Hye Choi、Jae-Ho Jeon、Jin-Kyung Kim、Jong-Gab Jun

  DOI：10.5012/bkcs.2010.31.04.965

  日期：2010.4.20

  An efficient and practical preparation of 2-arylbenzo[b]furan molecules including natural egonol, XH-14, ailanthoidol, and unnatural derivatives is demonstrated using Sonogashira coupling, iodine induced cyclization and Wittig reaction. Anti-inflammatory effects of the prepared benzo[b]furans were examined in lipopolysaccharide (LPS)-stimulated RAW 264-7 macrophages. The results showed that ailanthoidol, XH-14 and three other unnatural derivatives (9-10, 13) inhibited significantly the production of inflammatory mediator nitric oxide without showing cytotoxicity.

  展示了一种高效且实用的合成2-芳基苯并[b]呋喃分子的制备方法，包括天然的艾戈诺尔、XH-14、白蜡醇和一些非天然衍生物，采用了SonogashiRA偶联、碘诱导环化和Wittig反应。所制备的苯并[b]呋喃的抗炎作用在脂多糖（LPS）刺激的RAW 264-7巨噬细胞中进行了检测。结果显示，白蜡醇、XH-14和其他三种非天然衍生物（9-10，13）显著抑制了炎性介质一氧化氮的生成，并且未表现出细胞毒性。
• 2-phenylbenzofuran derivatives, method for preparing the same and use of the same for treating inflammatory disease
  申请人：KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY

  公开号：US10053443B2

  公开（公告）日：2018-08-21

  The present invention relates to a novel 2-phenylbenzofuran derivative or a pharmaceutically acceptable salt thereof, a production method for the same, and a pharmaceutical composition for preventing or treating an inflammatory disease comprising the same as an active ingredient, and the novel 2-phenylbenzofuran derivative or the pharmaceutically acceptable salt thereof according to the present invention is outstandingly effective in suppressing NO, IL-6, and TNF-alpha induced by macrophages, and therefore can advantageously be used in a pharmaceutical composition for preventing or treating an inflammatory disease.

  本发明涉及一种新型 2-苯基苯并呋喃衍生物或其药学上可接受的盐、其生产方法以及一种用于预防或治疗炎症性疾病的药物组合物，其中包含该衍生物或其药学上可接受的盐作为活性成分，根据本发明的新型 2-苯基苯并呋喃衍生物或其药学上可接受的盐在抑制巨噬细胞诱导的 NO、IL-6 和 TNF-α 方面效果显著，因此可有利地用于预防或治疗炎症性疾病的药物组合物中。