Methyl 2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-(3-methoxy-3-oxopropyl)-1-benzofuran-3-carboxylate | 177714-96-4

• 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: Methyl 2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-(3-methoxy-3-oxopropyl)-1-benzofuran-3-carboxylate
• CAS: 177714-96-4
• 化学式: C₂₂H₂₂O₈
• 分子量: 414.412
• InChiKey: NSUUXWGPSWKLNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl 2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-(3-methoxy-3-oxopropyl)-1-benzofuran-3-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 2-(3-methoxy-4-hydroxyphenyl)-3-methoxycarbonyl-5-(3-hydroxypropyl)-7-methoxybenzo[b]furan
  参考文献：
  名称：

  Antileishmanial activity, cytotoxicity and QSAR analysis of synthetic dihydrobenzofuran lignans and related benzofurans

  摘要：

  A series of synthetic dihydrobenzofuran lignans and related benzofurans were evaluated for their cytotoxicity in a screening panel consisting of various human tumour cell lines, and for their antiprotozoal activity against L. donovani (axenic amastigotes), chloroquine resistant Plasmodium falciparum (strain K1), Trypanosoma brucei rhodesiense and T. cruzi, and for cytotoxicity on L6 cells. No promising cytotoxicities against human tumour cell lines were observed for newly synthesised compounds, but the dimerisation product of some lipophylic esters of caffeic acid, such as compound 2g, showed a high activity against chloroquine-resistant P. falciparum (strain K1) (IC50 0.43 mug/mL) and L. donovani (axenic amastigotes) (IC50 0.12 mug/mL), which was confirmed in an infected macrophage assay (IC50 0.19 mug/mL). QSAR models for the cytotoxic and antileishmanial activity were, generated using Quasar receptor surface modelling. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.058
• 作为产物：
  描述：

  methyl (E)-3-[2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl]-prop-2-enoate 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氨 、 氢气 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 生成 Methyl 2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-(3-methoxy-3-oxopropyl)-1-benzofuran-3-carboxylate
  参考文献：
  名称：

  Antileishmanial activity, cytotoxicity and QSAR analysis of synthetic dihydrobenzofuran lignans and related benzofurans

  摘要：

  A series of synthetic dihydrobenzofuran lignans and related benzofurans were evaluated for their cytotoxicity in a screening panel consisting of various human tumour cell lines, and for their antiprotozoal activity against L. donovani (axenic amastigotes), chloroquine resistant Plasmodium falciparum (strain K1), Trypanosoma brucei rhodesiense and T. cruzi, and for cytotoxicity on L6 cells. No promising cytotoxicities against human tumour cell lines were observed for newly synthesised compounds, but the dimerisation product of some lipophylic esters of caffeic acid, such as compound 2g, showed a high activity against chloroquine-resistant P. falciparum (strain K1) (IC50 0.43 mug/mL) and L. donovani (axenic amastigotes) (IC50 0.12 mug/mL), which was confirmed in an infected macrophage assay (IC50 0.19 mug/mL). QSAR models for the cytotoxic and antileishmanial activity were, generated using Quasar receptor surface modelling. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.058

文献信息

• 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。
• Antileishmanial activity, cytotoxicity and QSAR analysis of synthetic dihydrobenzofuran lignans and related benzofurans
  作者：Sabine Van Miert、Stefaan Van Dyck、Thomas J. Schmidt、Reto Brun、Arnold Vlietinck、Guy Lemière、Luc Pieters

  DOI：10.1016/j.bmc.2004.10.058

  日期：2005.2

  A series of synthetic dihydrobenzofuran lignans and related benzofurans were evaluated for their cytotoxicity in a screening panel consisting of various human tumour cell lines, and for their antiprotozoal activity against L. donovani (axenic amastigotes), chloroquine resistant Plasmodium falciparum (strain K1), Trypanosoma brucei rhodesiense and T. cruzi, and for cytotoxicity on L6 cells. No promising cytotoxicities against human tumour cell lines were observed for newly synthesised compounds, but the dimerisation product of some lipophylic esters of caffeic acid, such as compound 2g, showed a high activity against chloroquine-resistant P. falciparum (strain K1) (IC50 0.43 mug/mL) and L. donovani (axenic amastigotes) (IC50 0.12 mug/mL), which was confirmed in an infected macrophage assay (IC50 0.19 mug/mL). QSAR models for the cytotoxic and antileishmanial activity were, generated using Quasar receptor surface modelling. (C) 2004 Elsevier Ltd. All rights reserved.