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

Abstract

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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QIAN Xu-Hong, ZHANG Yu-Lan, XU Xiao-Yong, TAO Zhi-Fu. Syntheses,DNA Intercalation Activities and Molecular Modelling on Structures of Tatramethyldifuronaphthalenes[J]. Chem. J. Chinese Universities, 1996, 17(9): 1399.

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

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