methyl (E)-3-<2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methoxycarbonylbenzofuran-5-yl>propenoate | 162439-94-3

• 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 (E)-3-<2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methoxycarbonylbenzofuran-5-yl>propenoate
• 英文别名: methyl 2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-[(E)-3-methoxy-3-oxoprop-1-enyl]-1-benzofuran-3-carboxylate
• CAS: 162439-94-3
• 化学式: C₂₂H₂₀O₈
• 分子量: 412.396
• InChiKey: PVTQIFRQAKFATG-VMPITWQZSA-N

物化性质

• 熔点：
  174 °C
• 沸点：
  589.098±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.301±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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 (E)-3-<2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methoxycarbonylbenzofuran-5-yl>propenoate 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 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
• 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 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 以20%的产率得到methyl (E)-3-<2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methoxycarbonylbenzofuran-5-yl>propenoate
  参考文献：
  名称：

  氧化偶联反应生物活性木脂素的制备研究。I.与精神分裂素有关的苯并呋喃木脂素的制备及其脂质过氧化抑制作用。

  摘要：

  通过明智地使用氧化偶联反应，有效地制备了裂殖壶菌素1-3的母体苯并呋喃木脂素4和相关化合物，并测试了它们对大鼠脑匀浆和大鼠肝微粒体中脂质过氧化的抑制作用。在大鼠脑匀浆中测试的十二种化合物中，化合物13、14和16显示出显着的抑制活性。然后在大鼠肝微粒体中测试了化合物13和16，发现它们的活性比schizotenuin A（1）更强，并且比（+/-）-α-生育酚更强。

  DOI：

  10.1248/cpb.42.2500

文献信息

• Studies on the Preparation of Bioactive Lignans by Oxidative Coupling Reaction. I. Preparation and Lipid Peroxidation Inhibitory Effect of Benzofuran Lignans Related to Schizotenuins.
  作者：Shirou MAEDA、Hiroshi MASUDA、Takashi TOKOROYAMA

  DOI：10.1248/cpb.42.2500

  日期：——

  The parent benzofuran lignan 4 of schizotenuins 1-3 and related compounds were efficiently prepared by a judicious use of the oxidative coupling reaction, and were tested for their inhibitory effects on lipid peroxidation in rat brain homogenate and rat liver microsomes. Among twelve compounds tested in rat brain homogenate, compounds 13, 14 and 16 showed prominent inhibitory activity. Compounds 13

  通过明智地使用氧化偶联反应，有效地制备了裂殖壶菌素1-3的母体苯并呋喃木脂素4和相关化合物，并测试了它们对大鼠脑匀浆和大鼠肝微粒体中脂质过氧化的抑制作用。在大鼠脑匀浆中测试的十二种化合物中，化合物13、14和16显示出显着的抑制活性。然后在大鼠肝微粒体中测试了化合物13和16，发现它们的活性比schizotenuin A（1）更强，并且比（+/-）-α-生育酚更强。
• 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.