3-(2-(3,4-dimethoxyphenyl)-7-methoxybenzofuran-5-yl)propyl acetate | 17375-67-6

• 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
• 英文名称: 3-(2-(3,4-dimethoxyphenyl)-7-methoxybenzofuran-5-yl)propyl acetate
• 英文别名: 3-[2-(3,4-dimethoxyphenyl)-7-methoxy-1-benzofuran-5-yl]propyl acetate；5-(3-acetoxypropyl)-2-(3,4-dimethoxyphenyl)-7-methoxybenzofuran
• CAS: 17375-67-6
• 化学式: C₂₂H₂₄O₆
• 分子量: 384.429
• InChiKey: VSFQCLNRSJUEAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  67.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(2-(3,4-dimethoxyphenyl)-7-methoxybenzofuran-5-yl)propyl acetate 在 甲醇 、 sodium hydroxide 作用下， 以90%的产率得到3-[2-(3,4-二甲氧基苯基)-7-甲氧基苯并呋喃-5-基]-1-丙醇
  参考文献：
  名称：

  苯并噻吩酚，烯醇及相关类似物的全合成

  摘要：

  已开发出有效且通用的合成方案，用于全合成艾兰地洛尔，烯醇和一些相关类似物。这里描述的关键转化涉及苯并呋喃和Sonogashira偶联的两步构建，并且从容易获得的试剂开始证明是方便有效的。 苯并呋喃-交叉偶联-McMurry反应-Sonogashira偶联-天然产物

  DOI：

  10.1055/s-0029-1219224
• 作为产物：
  描述：

  3,4-二甲氧基苯乙炔 在 copper(l) iodide 、 lithium aluminium tetrahydride 、 palladium 10% on activated carbon 、 溶剂黄146 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 48.67h， 生成 3-(2-(3,4-dimethoxyphenyl)-7-methoxybenzofuran-5-yl)propyl acetate
  参考文献：
  名称：

  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

  摘要：

  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。

  公开号：

  US20160332980A1

文献信息

• Total Synthesis of Ailanthoidol, Egonol, and Related Analogues
  作者：Xin-Fang Duan、Gang Shen、Zhan-Bin Zhang

  DOI：10.1055/s-0029-1219224

  日期：2010.4

  Efficient and general synthetic protocols were developed for the total synthesis of ailanthoidol, egonol, and some related analogues. The key transformations describe here involve a two-step construction of the benzofuran and a Sonogashira coupling, and proved to be convenient and effective, starting from readily available reagents. benzofurans - cross-coupling - McMurry reaction - ­Sonogashira coupling

  已开发出有效且通用的合成方案，用于全合成艾兰地洛尔，烯醇和一些相关类似物。这里描述的关键转化涉及苯并呋喃和Sonogashira偶联的两步构建，并且从容易获得的试剂开始证明是方便有效的。 苯并呋喃-交叉偶联-McMurry反应-Sonogashira偶联-天然产物
• 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。
• Cyclooxygenase inhibitory properties of<i>nor</i>-neolignans from<i>Styrax pohlii</i>
  作者：Camila S. Bertanha、Caio G. Braguine、Ana C.G. Moraes、Valéria M.M. Gimenez、Milton Groppo、Márcio L.A. Silva、Wilson R. Cunha、Ana H. Januário、Patrícia M. Pauletti

  DOI：10.1080/14786419.2012.671320

  日期：2012.12

  Chemical investigation of the n-hexane and EtOAc fractions of the ethanolic extract from Styrax pohlii (Styracaceae) aerial parts resulted in the isolation of the benzofuran nor-neolignan derivatives egonol (1), homoegonol (2), homoegonol gentiobioside (3), homoegonol glucoside (4) and egonol gentiobioside (5). This is the first report of compounds 1-5 in S. pohlii. Compounds 1-5, the acetyl derivatives 1a and 2a, the ethanolic extract (EE), the n-hexane fraction (HF) and EtOAc fraction (EF) were tested for their inhibitory activities against COX-1 and COX-2. The results showed that EE, HF, EF and compounds 1-5 and 1 a-2 a shown weak to moderate inhibition of COX-1 and COX-2. Among the assayed nor-neolignans, 4 gave a COX-1 inhibition of 35.7% at 30 mu M. Compound 5 displayed a COX-2 inhibition of 19.7% at 30 mu M.
• 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。
• A Convenient Two-Step Synthesis of 2-Arylbenzofurans
  作者：Xin-Fang Duan、Jian-Xia Feng、Zhan-Bin Zhang

  DOI：10.1055/s-0029-1217129

  日期：2010.2

  A novel and convenient two-step synthesis of 2-arylbenzofurans is described which proceeds via a selective cross-pinacol-type coupling between a salicylaldehyde and an aromatic aldehyde, followed by an acid-promoted cyclization. One advantage of this method is that separation of the three possible pinacol products that can form during the cross-coupling is not necessary. This method is also applied to the synthesis of the 2-arylbenzofuran-containing natural product, homoegonol.

  该方法通过水杨醛和芳香醛之间的选择性交叉频哪醇型偶联，然后进行酸促进环化，从而合成 2-芳基苯并呋喃。这种方法的优点之一是无需分离交叉偶联过程中可能形成的三种频哪醇产物。这种方法还可用于合成含 2-芳基苯并呋喃的天然产物高根醇。