2-[(Z)-2-[3-(ethoxymethoxy)-4-methoxyphenyl]ethenyl]naphthalene | 845624-61-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-[(Z)-2-[3-(ethoxymethoxy)-4-methoxyphenyl]ethenyl]naphthalene
• CAS: 845624-61-5
• 化学式: C₂₂H₂₂O₃
• 分子量: 334.415
• InChiKey: SEQWYMWBLUEXQH-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(Z)-2-[3-(ethoxymethoxy)-4-methoxyphenyl]ethenyl]naphthalene 在 盐酸 作用下， 以 甲醇 为溶剂， 以70%的产率得到(Z)-2-methoxy-5-[2-(naphth-2-yl)vinyl]phenol
  参考文献：
  名称：

  康他汀A-4萘类似物的设计，合成和细胞毒活性。

  摘要：

  康柏他汀A-4的3,4,5-三甲氧基苯基和3-羟基-4-甲氧基苯基环被认为对于其作为抗有丝分裂剂的活性是最佳的。用萘环取代任一化合物，所得化合物的效力可与母体化合物相当。这些结果表明，萘环是康美他汀A-4的3,4,5-三甲氧基苯基或3-羟基-4-甲氧基苯基的良好替代物，并且它们都不是抗肿瘤活性所必需的。

  DOI：

  10.1016/s0960-894x(00)00506-0
• 作为产物：
  描述：

  2-萘甲醇 在 正丁基锂 、 三溴化磷 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 苯 为溶剂， 反应 0.5h， 生成 2-[(Z)-2-[3-(ethoxymethoxy)-4-methoxyphenyl]ethenyl]naphthalene
  参考文献：
  名称：

  Further Naphthylcombretastatins. An Investigation on the Role of the Naphthalene Moiety

  摘要：

  By synthesis and biological studies of new naphthalene analogues of combretastatins, we have found that the naphthalene is a good surrogate for the isovanillin moiety (3-hydroxy-4methoxyphenyl) of combretastatin A-4, always generating highly cytotoxic analogues when combined with the 3,4,5-trimethoxyphenyl or related systems. On the other hand, when the naphthalene replaces the 3,4,5-trimethoxyphenyl moiety, the cytotoxic activity is largely decreased. The most cytotoxic naphthalene analogues of combretastatins, which also produce inhibition of tubulin polymerization, exerted their antimitotic effects through microtubule network disruption and subsequent G(2)/M arrest of the cell cycle in human cancer cells.

  DOI：

  10.1021/jm0310737

文献信息

• Design, synthesis and cytotoxic activities of naphthyl analogues of combretastatin A-4
  作者：Ana B.S. Maya、Benedicto del Rey、Rafael Pelaez Lamamie de Clairac、Esther Caballero、Isabel Barasoain、Jose Manuel Andreu、Manuel Medarde

  DOI：10.1016/s0960-894x(00)00506-0

  日期：2000.11

  3-hydroxy-4-methoxyphenyl rings of combretastatin A-4 are deemed optimal for its activity as antimitotic agent. The replacement of either one by a naphthalene ring results in compounds with a potency comparable to that of the parent compound. These results show that the naphthalene ring is a good surrogate for the 3,4,5-trimethoxyphenyl or the 3-hydroxy-4-methoxyphenyl rings of combretastatin A-4 and that neither of

  康柏他汀A-4的3,4,5-三甲氧基苯基和3-羟基-4-甲氧基苯基环被认为对于其作为抗有丝分裂剂的活性是最佳的。用萘环取代任一化合物，所得化合物的效力可与母体化合物相当。这些结果表明，萘环是康美他汀A-4的3,4,5-三甲氧基苯基或3-羟基-4-甲氧基苯基的良好替代物，并且它们都不是抗肿瘤活性所必需的。
• Further Naphthylcombretastatins. An Investigation on the Role of the Naphthalene Moiety
  作者：Ana B. S. Maya、Concepción Pérez-Melero、Carmen Mateo、Dulce Alonso、José Luis Fernández、Consuelo Gajate、Faustino Mollinedo、Rafael Peláez、Esther Caballero、Manuel Medarde

  DOI：10.1021/jm0310737

  日期：2005.1.1

  By synthesis and biological studies of new naphthalene analogues of combretastatins, we have found that the naphthalene is a good surrogate for the isovanillin moiety (3-hydroxy-4methoxyphenyl) of combretastatin A-4, always generating highly cytotoxic analogues when combined with the 3,4,5-trimethoxyphenyl or related systems. On the other hand, when the naphthalene replaces the 3,4,5-trimethoxyphenyl moiety, the cytotoxic activity is largely decreased. The most cytotoxic naphthalene analogues of combretastatins, which also produce inhibition of tubulin polymerization, exerted their antimitotic effects through microtubule network disruption and subsequent G(2)/M arrest of the cell cycle in human cancer cells.