2-(4'-methoxyphenyl)-1,8-naphthalic anhydride | 158922-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4'-methoxyphenyl)-1,8-naphthalic anhydride
• 英文别名: 2-(4-Methoxyphenyl)naphthalic anhydride；6-(4-methoxyphenyl)-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene-2,4-dione
• CAS: 158922-26-0
• 化学式: C₁₉H₁₂O₄
• 分子量: 304.302
• InChiKey: QJNMPLSUKPHYQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4'-methoxyphenyl)-1,8-naphthalic anhydride 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 9.0h， 以82%的产率得到2-(4'-hydroxyphenyl)-1,8-naphthalic anhydride
  参考文献：
  名称：

  Synthesis of 2-(4-Hydroxyphenyl)naphthalene-1,8-dicarboxylic Anhydride, a Phytoalexin Isolated from Unripe Banana (Musa acuminata)

  摘要：

  2-(4-羟基苯基)萘-1,8-二甲酸酐是从未成熟香蕉 (Musa acuminata) 果皮中分离出来的植物抗毒素的一种成分，由 3-溴苊合成。

  DOI：

  10.1271/bbb.63.1834
• 作为产物：
  描述：

  3-(4-methoxyphenyl)acenaphthene 在 sodium dichromate 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以63%的产率得到2-(4'-methoxyphenyl)-1,8-naphthalic anhydride
  参考文献：
  名称：

  Synthesis of 2-(4-Hydroxyphenyl)naphthalene-1,8-dicarboxylic Anhydride, a Phytoalexin Isolated from Unripe Banana (Musa acuminata)

  摘要：

  2-(4-羟基苯基)萘-1,8-二甲酸酐是从未成熟香蕉 (Musa acuminata) 果皮中分离出来的植物抗毒素的一种成分，由 3-溴苊合成。

  DOI：

  10.1271/bbb.63.1834

文献信息

• Synthesis and study of antiproliferative, antitopoisomerase II, DNA-intercalating and DNA-damaging activities of arylnaphthalimides
  作者：Patricia Quintana-Espinoza、Jonay García-Luis、Ángel Amesty、Patricia Martín-Rodríguez、Isabel Lorenzo-Castrillejo、Angel G. Ravelo、Leandro Fernández-Pérez、Félix Machín、Ana Estévez-Braun

  DOI：10.1016/j.bmc.2013.08.039

  日期：2013.11

  A series of arylnaphthalimides were designed and synthesized to overcome the dose-limiting cytotoxicity of N-acetylated metabolites arising from amonafide, the prototypical antitumour naphthalimide whose biomedical properties have been related to its ability to intercalate the DNA and poison the enzyme Topoisomerase II. Thus, these arylnaphthalimides were first evaluated for their antiproliferative activity against two tumour cell lines and for their antitopoisomerase II in vitro activities, together with their ability to intercalate the DNA in vitro and also through docking modelization. Then, the well-known DNA damage response in Saccharomyces cerevisiae was employed to critically evaluate whether these novel compounds can damage the DNA in vivo. By performing all these assays we conclude that the 5-arylsubstituted naphthalimides not only keep but also improve amonafide's biological activities. (C) 2013 Elsevier Ltd. All rights reserved.
• A phenalenone-type phytoalexin from Musa acuminata
  作者：Nobuhiro Hirai、Hiroki Ishida、Koichi Koshimizu

  DOI：10.1016/0031-9422(94)85064-x

  日期：1994.1

  The unripe green fruit of banana [Musa acuminata (AAA) cv Giant Cavendish] shows resistance to infection of Colletotrichum musae. Four antifungal compounds were detected in the extracts of the green fruits inoculated with conidia of the fungus. The two major compounds were identified as 2-(4'-hydroxyphenyl)-naphthalic anhydride and methyl 2-benzimidazole carbamate. The former is a new phytoalexin of the phenalenone type, and the latter is an antifungal agent derived from benomyl, but behaving like a phytoalexin.