Syntheses of 6-(2-hydroxy-6-phenylhexyl)-5,6-dihydro-2H-pyran-2-one derivatives and their cytotoxicities

被引：0
|
作者：
Ochi, Ryota [1 ]
Taniyama, Yasuhiko [1 ]
Nishiwaki, Hisashi [1 ]
Nishi, Kosuke [1 ]
Sugahara, Takuya [1 ]
Yamauchi, Satoshi [1 ]
机构：
[1] Ehime Univ, Grad Sch Agr, 3-5-7 Tarumi, Matsuyama, Ehime 7908566, Japan
来源：
PHYTOCHEMISTRY LETTERS | 2022年 / 52卷
关键词：
5; 6-dihydro-2H-pyran-2-one; Structure-activity relationship; Cytotoxicity; Oxetane; 6-ALKYLATED ALPHA-PYRONES; ABSOLUTE-CONFIGURATION; INHIBITORS;
D O I：
10.1016/j.phytol.2022.10.002
中图分类号：
Q94 [植物学];
学科分类号：
071001 ;
摘要：
The cytotoxicities against cancer cells (HL-60, HeLa) and insect cells (Sf9) of four stereoisomers of 6-(2-hydroxy- 6-phenylhexyl)-5,6-dihydro-2H-pyran-2-one (1) were evaluated, and then their structure-activity relationships examined. The 2 '-dehydroxy derivative 5 of (6 R,2 ' R)-and (6 R,2 ' S)-1 showed the highest activity against HeLa cells (IC50 = 1.4 mu M). To evaluate the effect of the 2 '-hydroxy group of 1, 6R-and 6S-oxetane derivatives were also synthesized and their activities examined. Against HeLa and HL-60 cells, the activities of the less potent stereoisomers were enhanced 3-4-fold by the introduction of the oxetane moieties at the 2 '-position. Against the insect cell line (Sf9), phenyl derivative 7 showed the highest activity with an IC50 value of 8.0 mu M.
引用
收藏
页码：118 / 121
页数：4
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