2-(3-methoxy-4-acetyloxyphenyl)-3-methoxycarbonyl-5-(3-methoxycarbonylethyl)-7-methoxybenzo[b]furan | 845883-08-1

• 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: 2-(3-methoxy-4-acetyloxyphenyl)-3-methoxycarbonyl-5-(3-methoxycarbonylethyl)-7-methoxybenzo[b]furan
• CAS: 845883-08-1
• 化学式: C₂₄H₂₄O₉
• 分子量: 456.449
• InChiKey: PULHJARMPDBHCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  110.5
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-(3-methoxy-4-acetyloxyphenyl)-3-methoxycarbonyl-5-(3-methoxycarbonylethyl)-7-methoxybenzo[b]furan 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 、 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 为溶剂， 生成 2-(3-methoxy-4-acetyloxyphenyl)-3-methoxycarbonyl-5-(3-methoxycarbonylethyl)-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

文献信息

• Synthesis and Cytotoxicity of Novel Benzofuran Neolignan Derivatives
  作者：Hua-Fang Fan、Ying-Mei Ren、Xiu-Ling Wu、Qiu-An Wang

  DOI：10.3184/030823410x12709997864719

  日期：2010.4

  A series of 10 related benzofuran neolignan derivatives were obtained by utilising a biomimetic reaction sequence involving oxidative dimerisation of methyl ferulate, followed by derivatisation reactions. The structures of the new compounds were confirmed by 1H NMR, elemental analysis, MS and IR. All compounds were evaluated for their cytotoxic potential against five human cancer cell lines (HL-60

  通过利用涉及阿魏酸甲酯氧化二聚化和衍生化反应的仿生反应序列，获得了一系列 10 种相关的苯并呋喃新木脂素衍生物。新化合物的结构经1H NMR、元素分析、MS和IR确证。通过标准 MTT 方法评估所有化合物对五种人类癌细胞系（HL-60、SMMC-7721、A-549、SK-BR-3 和 PAN-1）的细胞毒性潜力。结果表明，它们中的大多数表现出有效的细胞毒性。