1-bromo-2-methoxy-5-(3,4,5-trimethoxyphenyl)naphthalene | 1375679-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-bromo-2-methoxy-5-(3,4,5-trimethoxyphenyl)naphthalene
• CAS: 1375679-78-9
• 化学式: C₂₀H₁₉BrO₄
• 分子量: 403.272
• InChiKey: JFLLAPDDMWWKCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-bromo-2-methoxy-5-(3,4,5-trimethoxyphenyl)naphthalene 在 copper(l) iodide 、 sodium azide 、 水 、 sodium ascorbate 、 N,N'-二甲基乙二胺 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以46%的产率得到2-methoxy-5-(3,4,5-trimethoxyphenyl)naphthalen-1-amine
  参考文献：
  名称：

  Conformationnally restricted naphthalene derivatives type isocombretastatin A-4 and isoerianin analogues: Synthesis, cytotoxicity and antitubulin activity

  摘要：

  A novel series of dihydronaphtalene, tetrahydronaphtalene and naphtalene derivatives as restricted analogues of isoCA-4 were designed, synthesized and evaluated for their anticancer properties. High cell growth inhibition against four tumour cell lines was observed at a nanomolar level with dihydronaphtalenes 1d, e and 1h, tetrahydronaphtalene 2c and naphtalene 3c. Structure activity relationships are also considered. These compounds exhibited a significant inhibitory activity toward tubulin polymerization (IC50 = 2-3 mu M), comparable to that of isoCA-4. The effect of the lead compounds le and 2c on the cancer cells tested was associated with cell cycle arrest in the G(2)/M phase. Docking studies reveal that these compounds showed a binding mode similar to those observed with their non-constraint isoCA-4 and isoerianin congeners. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.001
• 作为产物：
  描述：

  5-溴-6-甲氧基-1-四氢萘酮 在 tris-(dibenzylideneacetone)dipalladium(0) 、 magnesium sulfate 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium tert-butoxide 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 1-bromo-2-methoxy-5-(3,4,5-trimethoxyphenyl)naphthalene
  参考文献：
  名称：

  Conformationnally restricted naphthalene derivatives type isocombretastatin A-4 and isoerianin analogues: Synthesis, cytotoxicity and antitubulin activity

  摘要：

  A novel series of dihydronaphtalene, tetrahydronaphtalene and naphtalene derivatives as restricted analogues of isoCA-4 were designed, synthesized and evaluated for their anticancer properties. High cell growth inhibition against four tumour cell lines was observed at a nanomolar level with dihydronaphtalenes 1d, e and 1h, tetrahydronaphtalene 2c and naphtalene 3c. Structure activity relationships are also considered. These compounds exhibited a significant inhibitory activity toward tubulin polymerization (IC50 = 2-3 mu M), comparable to that of isoCA-4. The effect of the lead compounds le and 2c on the cancer cells tested was associated with cell cycle arrest in the G(2)/M phase. Docking studies reveal that these compounds showed a binding mode similar to those observed with their non-constraint isoCA-4 and isoerianin congeners. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.001

文献信息

• Conformationnally restricted naphthalene derivatives type isocombretastatin A-4 and isoerianin analogues: Synthesis, cytotoxicity and antitubulin activity
  作者：Evelia Rasolofonjatovo、Olivier Provot、Abdallah Hamze、Jordi Rodrigo、Jérome Bignon、Joanna Wdzieczak-Bakala、Déborah Desravines、Joëlle Dubois、Jean-Daniel Brion、Mouad Alami

  DOI：10.1016/j.ejmech.2012.03.001

  日期：2012.6

  A novel series of dihydronaphtalene, tetrahydronaphtalene and naphtalene derivatives as restricted analogues of isoCA-4 were designed, synthesized and evaluated for their anticancer properties. High cell growth inhibition against four tumour cell lines was observed at a nanomolar level with dihydronaphtalenes 1d, e and 1h, tetrahydronaphtalene 2c and naphtalene 3c. Structure activity relationships are also considered. These compounds exhibited a significant inhibitory activity toward tubulin polymerization (IC50 = 2-3 mu M), comparable to that of isoCA-4. The effect of the lead compounds le and 2c on the cancer cells tested was associated with cell cycle arrest in the G(2)/M phase. Docking studies reveal that these compounds showed a binding mode similar to those observed with their non-constraint isoCA-4 and isoerianin congeners. (C) 2012 Elsevier Masson SAS. All rights reserved.