[Synthesis of chrysin derivatives and their interaction with DNA].
Using chrysin as a leading compound, intermediate 5, 7-dihydroxy-6, 8-bis (hydroxymethyl) flavone (1) was synthesized by hydroxymethylation. The intermediate reacted with different alcohols to afford 5, 7-dihydroxy-6, 8-bis ( methoxymethyl) flavone (2), 6, 8-bis (ethoxymethyl) -5, 7dihydroxyflavone (3), 6, 8-bis-(butoxymethyl)-5, 7-dihydroxyflavone (4), 6, 8-bis (pentyloxymethyl) -5,7-dihydroxy flavone (5) and 6, 8-bis-(ethoxymethyl) -5-hydroxy-7-methoxyflavone (6). These compounds were characterized by IR, 1H NMR, 13C NMR and element analysis. The crystal structure of 6 was determined by X-ray crystal diffraction. The interaction of the derivatives with CT-DNA was studied by fluorescent spectroscopy. According to the Stern-Volmer equation, the quenching constants of the compounds 1 - 4 were measured, separately, they were K(q1) = 9.71 x 10(3) L x mol(-1), K(q2) = 2.25 x 10(4) L x mol(-1), K(q3) = 1.03 x 10(4) L x mol(-1) and K(q4) = 7.96 x 10(3) L x mol(-1). Compounds 1-4 showed higher binding affinity with DNA than chrysin did. The results provided the experimental basis for developing a more effective flavonoid and worthing further thoroughly study.
Zhang
Zun-Ting
ZT
School of Chemistry and Materials Science, Shaanxi Normal University, Xi'an 710062, China. zhangzt@snnu.edu.cn
Chen
Li-Li
LL
D000818:Animals; D003461:Crystallography; D004247:DNA / Q000378:metabolism*; D004347:Drug Interactions; D047309:Flavones / Q000138:chemical synthesis* / Q000737:chemistry; D005419:Flavonoids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D014961:X-Ray Diffraction
C541891:6,8-bis-(ethoxymethyl) -5-hydroxy-7-methoxyflavone; D047309:Flavones; D005419:Flavonoids; C043561:chrysin; D004247:DNA; C427203:calf thymus DNA