文献类型：期刊文献

英文题名：Syntheses, DNA intercalation activities and molecular modelling on structures of tatramethyldifuronaphthalenes

作者：Qian, XH; Zhang, YL; Xu, XY; Tao, ZF

年份：1996

卷号：17

期号：9

起止页码：1399

外文期刊名：CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE

收录：;WOS:【SCI-EXPANDED(收录号:WOS:A1996VJ91600016)】；

语种：英文

外文关键词：difuronaphthalene; synthesis; DNA intercalation; structure characterization; molecular modelling

摘要：2,7-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 tetramethyidifuronaphthalene 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, H-1 NMR, C-13 NMR, MS and 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 DNA intercalation activity between 4 and 5 mainly depends on that in their molecular planarity.