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

Abstract

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

CLC Number:

O621

Cite this article

TAO ZHIFU;QIAN XUHONG;SONG GONGHUA. Synthesis, characterization and DNA intercalation of a furonaphthopyronone as a novel analogue of furocoumarin[J]. Chin. J. Org. Chem., 1997, 17(5): 428-432.

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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