5-(3-hydroxypropyl)-7-methoxy-3-methyl-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran | 36307-23-0

• 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: 5-(3-hydroxypropyl)-7-methoxy-3-methyl-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran
• 英文别名: 5-(3-hydroxypropyl)-7-methoxy-3-(methylbenzofuran-2-yl)-3-methoxyphenol；3-[2-(4-hydroxy-3-methoxy-phenyl)-7-methoxy-3-methyl-benzofuran-5-yl]-propan-1-ol；2-(4-Hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-3-methylbenzofuran；Phenylcoumaron；4-[5-(3-Hydroxypropyl)-7-methoxy-3-methyl-1-benzofuran-2-yl]-2-methoxyphenol
• CAS: 36307-23-0
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: INIDFZVTJWLLLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(3-hydroxypropyl)-7-methoxy-3-methyl-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran 在 selenium(IV) oxide 作用下， 以 乙醇 为溶剂， 以72 %的产率得到5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)-3-benzo[b]furan-carbaldehyde
  参考文献：
  名称：

  作为强效微管抑制剂的丹参衍生物的合成及构效关系

  摘要：

  Salvinal 是一种从丹参 (丹参) 的根中分离出来的天然木酚素。先前的研究已经证明其在药物敏感和耐药癌细胞系中均具有抗增殖活性，IC50 值范围为 4–17 µM。在这项研究中，合成了一系列鼠尾草醛衍生物并评估了构效关系。在24种丹参衍生物中，有6种化合物的抗癌活性优于丹参。化合物 25 显示出出色的抗癌活性，对 KB、KB-Vin10（过表达 MDR/Pgp）和 KB-7D（过表达 MRP）人癌细胞系的 IC50 值为 0.13–0.14 µM。基于我们的体外微管解聚试验，化合物 25 以剂量依赖的方式显示出解聚活性。

  DOI：

  10.3390/ijms24076386
• 作为产物：
  描述：

  5-溴香兰素 在 palladium on activated charcoal 四氢吡咯 、 吡啶 、 盐酸 、 ammonium hydroxide 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 potassium chloride 、 盐酸羟胺 、 氢气 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 为溶剂， 反应 64.0h， 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

文献信息

• CAFFEIC ACID DERIVATIVES FOR ANTI-ANGIOGENESIS
  申请人：Taipei Medical University

  公开号：US20160355493A1

  公开（公告）日：2016-12-08

  The present invention develops a series of methyl caffeate derivatives having biological activity in anti-angiogenesis. The present invention suggests that the compounds of the invention possess inhibiting angiogenesis through regulation of VEGF/VEGFR-2 and its downstream signaling cascades in the vascular endothelial cells (VECs).

  本发明开发了一系列具有抗血管生成生物活性的甲基咖啡酸衍生物。本发明表明，本发明的化合物通过调节血管内皮细胞（VECs）中的VEGF/VEGFR-2及其下游信号级联来抑制血管生成。
• A concise and efficient synthesis of salvinal from isoeugenol via a phenoxenium ion intermediate
  作者：Eng-Chi Wang、Yung-Shung Wein、Yueh-Hsiung Kuo

  DOI：10.1016/j.tetlet.2006.10.131

  日期：2006.12

  In this letter, we describe how salvinal can be efficiently synthesized from isoeugenol via a phenoxenium ion intermediate by four steps in 23% over all total yield. (c) 2006 Elsevier Ltd. All rights reserved.
• Adler; Stenemur, Chemische Berichte, 1956, vol. 89, p. 291,301
  作者：Adler、Stenemur

  DOI：——

  日期：——
• 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
  作者：Zhen Yang、Han Biao Liu、Chi Ming Lee、Hson Mou Chang、Henry N. C. Wong

  DOI：10.1021/jo00052a046

  日期：1992.12

  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.
• Synthesis and Structure–Activity Relationship of Salvinal Derivatives as Potent Microtubule Inhibitors
  作者：Chi-I Chang、Cheng-Chih Hsieh、Yung-Shung Wein、Ching-Chuan Kuo、Chi-Yen Chang、Jrhau Lung、Jong-Yuh Cherng、Po-Chen Chu、Jang-Yang Chang、Yueh-Hsiung Kuo

  DOI：10.3390/ijms24076386

  日期：——

  activity in both drug-sensitive and -resistant cancer cell lines, with IC50 values ranging from 4–17 µM. In this study, a series of salvinal derivatives was synthesized and evaluated for the structure–activity relationship. Among the twenty-four salvinal derivatives, six compounds showed better anticancer activity than salvinal. Compound 25 displayed excellent anticancer activity, with IC50 values of 0

  Salvinal 是一种从丹参 (丹参) 的根中分离出来的天然木酚素。先前的研究已经证明其在药物敏感和耐药癌细胞系中均具有抗增殖活性，IC50 值范围为 4–17 µM。在这项研究中，合成了一系列鼠尾草醛衍生物并评估了构效关系。在24种丹参衍生物中，有6种化合物的抗癌活性优于丹参。化合物 25 显示出出色的抗癌活性，对 KB、KB-Vin10（过表达 MDR/Pgp）和 KB-7D（过表达 MRP）人癌细胞系的 IC50 值为 0.13–0.14 µM。基于我们的体外微管解聚试验，化合物 25 以剂量依赖的方式显示出解聚活性。