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有机化学
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有机化学 ›› 1997, Vol. 17 ›› Issue (5): 428-432. 上一篇    下一篇

研究论文

一种新型呋喃香豆素类似物: 呋喃并萘并吡喃酮的合成及DNA嵌入活性

陶志福;钱旭红;宋恭华   

  1. 华东理工大学药物化工研究所
  • 发布日期:1997-10-25

Synthesis, characterization and DNA intercalation of a furonaphthopyronone as a novel analogue of furocoumarin

TAO ZHIFU;QIAN XUHONG;SONG GONGHUA   

  • Published:1997-10-25

1,5-萘二酚经Pechmann缩合，烯丙基醚化，Claisen重排，乙酰化，溴加成，闭环六步反应，合成了一个新型的呋喃香豆素类似物，2H-4,8-二甲基呋喃并[2',3':5,6]萘并[1,2-b]吡喃-2-酮(6)。所得2～6的5个新化合物的结构均经^1H NMR，MS，IR，元素分析确证，测试了化合物6的紫外及荧光光谱。在DMSO-Tris HCl体系中，用荧光淬灭技术考察了6和7的DNA嵌入活性，求取了Scatchard表观嵌入常数，发现6和7都能有效地嵌入小牛胸腺DNA中，6的嵌入活性小于7。

关键词: 萘二酚 P, 闭环反应, 吡喃酮 P, 脱氧核糖核酸, 克莱森重排, 有机合成, 呋喃 P, 缩合反应, 生物活性, 萘 P

As a novel analogue of furocoumarin, 2H-4,8-dimethylfuro [2',3':5,6]naphthol[1,2-b]pyran-2-one 6 was synthesized through Pechmann condensation, etherification, Claisen rearrangement, acetylation, bromine addition and cyclization of 1,5-naphthalenediol. The structures of 6 and its precusors were fully characterized by ^1H NMR, MS, IR and elemental analysis. The DNA-intercalative activity of 6 and 7 was investigated in DMSO-Tris HCl system and their apparent Scatchard binding constants were calculated. It was found that 7 intercalate into DNA more efficiently than 6 due to the different substituents on the furan ring.

Key words: NAPHTHALENEDIOL P, PYRANONE P, RING CLOSURE REACTION, CONDENSATION REACTION, CLAISEN REARRANGEMENT, FURAN P, ORGANIC SYNTHESIS, BIOLOGICAL ACTIVITY, NAPHTHALENE P, DEOXYRIBONUCLEIC ACID

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