高等学校化学学报

高等学校化学学报 ›› 1996, Vol. 17 ›› Issue (9): 1399.

• 论文 • 上一篇    下一篇

四甲基萘并二呋喃的合成和DNA嵌入性能及其结构的分子模拟研究

钱旭红, 张玉兰, 徐晓勇, 陶志福   

  1. 华东理工大学药物化工研究所, 上海, 200237
  • 收稿日期:1995-09-12 出版日期:1996-09-24 发布日期:1996-09-24
  • 通讯作者: 钱旭红,男,34岁,博士,教授.
  • 作者简介:钱旭红,男,34岁,博士,教授.
  • 基金资助:

    国家教育委员会基金;国家自然科学基金;洪堡基金(AVH)

Syntheses,DNA Intercalation Activities and Molecular Modelling on Structures of Tatramethyldifuronaphthalenes

QIAN Xu-Hong, ZHANG Yu-Lan, XU Xiao-Yong, TAO Zhi-Fu   

  1. Institute of Pesticides and Pharm., East China Univ, of Sci. and Tech, Shanghai, 200237
  • Received:1995-09-12 Online:1996-09-24 Published:1996-09-24

PDF (PC)

被引次数

10

摘要： 将2,7-二羰烷氧基萘(2)在三氯氧磷中环化成73%不对称及27%对称的四甲基萘并二呋喃(4和5).在盐酸作用下2环化成3,随后在乙酰乙酸乙酯/二氯甲烷中及三溴化硼作用下生成区域选择性环化产物(5).采用荧光强度测定法发现4对小牛胸腺DNA有嵌入作用。分子模拟方法指出4与5在DNA嵌入性能上的差别主要是由它们分子平面性不同所致。

关键词: 萘并二呋喃, 合成, DNA嵌入, 结构表征, 分子模拟

Abstract: Dialkoxynaphthalene(2) formed from the condensation of 2, 7-dihydroxynaphthalene(1) with 3-chloro-2-butanone, refluxed in POCl3/CCl4 to give cyclized products of 73% asymmerical 4 and symmetrical tetramethyldifuronaphthalene 5.In the presence of hydrochloride,2 was partly cyclized to give 3,followed by cyclization at room temperature in acetylacetate/methylenechloride under the action of BBr3 to give only symmetrical product 5.The structures of all products was fully characterized using IR,UV,FL,1H NMR,13CNMR, MSand elementary analysis,It was found that 4 can intercalate into Calf Thymus DNA,but 5 couldn't, and the apparrent intercalation constant for 4 was recorded.Using molecular modelling study,not only the bond lengths and angles of 5 were calculated well, but also it is indicated that the difference in DNAintercalation activity between 4 and 5 mainly depends on that in their molecular planarity.

Key words: Difuronaphthalene, Synthesis, DNA intercalation, Structure characterization, Molecular modelling

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