文献类型：期刊文献

中文题名：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

英文题名：Synthesis, Characterization and DNA Intercalation of A furonaphthopyronone as A Novel Analogue of Furocoumarin

作者：陶志福[1];钱旭红[1];宋恭华[1]

机构：[1]华东理工大学药物化工研究所,上海200237

年份：1997

卷号：17

期号：5

起止页码：428

中文期刊名：有机化学

外文期刊名：Chinese Journal of Organic Chemistry

收录：CSTPCD;;Scopus;北大核心:【北大核心1996】；CSCD:【CSCD2011_2012】；

基金：国家自然科学基金;国家教委重点博士点基金;优秀年轻教师基金资助课题

语种：中文

中文关键词：萘并吡喃酮;呋喃香豆素;DNA嵌入活性;荧光淬灭

外文关键词：naphthopyrones, synthesis, characterization, DNA intercalative activity, flucres cence quenching

摘要：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-TrisHCl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。
As a novel analogue of furocoumarin, 2H - 4,8 - dimethylfuro[2' , 3' : 5,6 ]naphtho[ 1, 2 - b ] pyran - 2 - one 6 was sythesized through Pechmann condensation, etherification, Claisen rear rangement , acetylation , bromine addition and cyclization of 1 , 5 - naphthalenediol . The sructures 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 HC1 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 .