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KMID : 0043319950180060440
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Archives of Pharmacal Research
1995 Volume.18 No. 6 p.440 ~ p.448
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Polyoxygenated Flavones; Synthesis, Cytotoxicities and Antitumor Activity against ICR Mice Carrying S-180 Cells
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Song Gyu-Yong
Ahn Byung-Zun
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Abstract
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Fitty two flavones were synthesized from polyoxygenated dibenzoylmethanes which were obtained by a modified Baker-Venkatarman rearrangement, of 2-benzoyl oxyacetophenones. The following flavones among them showed good cytotoxic activities against L1210 and HL60 cells ; 2’-benzoyloxy-5,7-dimethoxyflavone , 2’-benzyloxy-5,7,8-trimethoxyflavone , 2’-hydroxy-5,7,8-trimethoxyflavone , 2’-benzyloxy-5-hydroxyflavone , and 5,2’-dihydroxyflavone . Presence of 5-methoxy group potentiated the cytotoxic activity, while the existence of 7-methoxy group decreased the activity. 5-Hydroxy or methoxy activates 4-carbonyl group, while 7-methoxy group deactivates the acrbonyl group. From these observation it was concluded that the activation of carbonyl group at C-4 of a flavone is important for the enahncement of the cytotoxic activity. The presence of both 5-hydroxy and 2-benzyloxy-or 2-hydroxy group enhanced the antitumor activity; 2’-benzyloxy-5-hydroxy-7-methoxyflaone 9T/C=144%), 5.2’-dihydroxy-7-methoxyflavone (T/C=132%) and 5,2’-dihydroxy-6,78,6’ trtramethoxyflvone (T/C = 172%) 2’hexanolytion of 5,2’-dihydroxy-flavones did not improve the natitumor activity; 2’ hexanoyloxy-5-hydroxy-7-methoxyflavone showed T/C = 132%, about the same as that of 5,2’-dihydroxy-7-methoxyflvone (T/C=130%)
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KEYWORD
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Flavone synthesis, Antitumor activity, Structre-activity relationship
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