(E)-5-[3-(3,4-dimethoxyphenyl)prop-1-enyl]-1,2,3-trimethoxybenzene | 1215204-91-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-5-[3-(3,4-dimethoxyphenyl)prop-1-enyl]-1,2,3-trimethoxybenzene
• 英文别名: 5-[(E)-3-(3,4-dimethoxyphenyl)prop-1-enyl]-1,2,3-trimethoxybenzene
• CAS: 1215204-91-3
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: DXFDVPUIZMQWMR-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲基丁香酚 、 3,4,5-三甲氧基苯硼酸 在 palladium diacetate 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以3.5 mg的产率得到1,2-dimethoxy-4-(3-(3,4,5-trimethoxyphenyl)prop-1-enyl)benzene
  参考文献：
  名称：

  Design and pharmacophore modeling of biaryl methyl eugenol analogs as breast cancer invasion inhibitors

  摘要：

  Cell invasion and migration are required for the parent solid tumor cells to metastasize to distant organs. Microtubules form a polarized network, enabling organelle and protein movement throughout the cell. Cytoskeletal elements coordinately regulate cell's motility, adhesion, migration, exocytosis, endocytosis, and division. Thus, microtubule disruption can be a useful target to control cancer cell invasion and metastasis. The phenolic ether methyl eugenol (1), the major component of the essential oil of the leaves of Melaleuca ericifolia Sm. (Myrtaceae), was used as a starting scaffold to design eleven new and three known anti-tubulin agents 2-15 using carbon-carbon coupling reactions. A computer-assisted approach was used to design these new biaryl derivatives using colchicine-binding site of tubulin as the molecular target and colchicine as an active ligand. Several derivatives showed potent inhibitory activity against MDA-MB-231 cell migration at the 1-4 mu M dose range. The Z isomers, 4 and 15 were more active as invasion inhibitors compared to their structurally related E isomers, 2 and 14. The cytotoxic activities of compounds 2-15 against two breast cancer cell lines MDA-MB-231 and MCF-7 were evaluated. Anti-invasive activity of the semisynthetic derivatives is not due to a direct cytotoxic effect on MDA-MB-231. Analogs 2-15 may promote their anti-invasive activity through the induction of changes in cell morphology. A pharmacophore model was generated involving seven essential features for activity, which was consistent with a previously generated colchicine site inhibitors model. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.019

文献信息

• Design and pharmacophore modeling of biaryl methyl eugenol analogs as breast cancer invasion inhibitors
  作者：Fatma M. Abdel Bar、Mohammad A. Khanfar、Ahmed Y. Elnagar、Farid A. Badria、Ahmed M. Zaghloul、Kadria F. Ahmad、Paul W. Sylvester、Khalid A. El Sayed

  DOI：10.1016/j.bmc.2009.12.019

  日期：2010.1

  Cell invasion and migration are required for the parent solid tumor cells to metastasize to distant organs. Microtubules form a polarized network, enabling organelle and protein movement throughout the cell. Cytoskeletal elements coordinately regulate cell's motility, adhesion, migration, exocytosis, endocytosis, and division. Thus, microtubule disruption can be a useful target to control cancer cell invasion and metastasis. The phenolic ether methyl eugenol (1), the major component of the essential oil of the leaves of Melaleuca ericifolia Sm. (Myrtaceae), was used as a starting scaffold to design eleven new and three known anti-tubulin agents 2-15 using carbon-carbon coupling reactions. A computer-assisted approach was used to design these new biaryl derivatives using colchicine-binding site of tubulin as the molecular target and colchicine as an active ligand. Several derivatives showed potent inhibitory activity against MDA-MB-231 cell migration at the 1-4 mu M dose range. The Z isomers, 4 and 15 were more active as invasion inhibitors compared to their structurally related E isomers, 2 and 14. The cytotoxic activities of compounds 2-15 against two breast cancer cell lines MDA-MB-231 and MCF-7 were evaluated. Anti-invasive activity of the semisynthetic derivatives is not due to a direct cytotoxic effect on MDA-MB-231. Analogs 2-15 may promote their anti-invasive activity through the induction of changes in cell morphology. A pharmacophore model was generated involving seven essential features for activity, which was consistent with a previously generated colchicine site inhibitors model. (C) 2009 Elsevier Ltd. All rights reserved.