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
相关论文
共 50 条
  • [31] DERIVATIVES OF 2-ALKOXY-5,6-DIHYDRO-2H-PYRAN AS SUBSTRATES IN SYNTHESIS OF MONOSACCHARIDES .24. SYNTHESIS OF 6-ACYL DERIVATIVES FROM 6-CYANO-2-METHOXY-5,6-DIHYDRO-2H-PYRAN
    BELNIAK, K
    ZAMOJSKI, A
    ROCZNIKI CHEMII, 1977, 51 (7-8): : 1545 - 1547
  • [32] Stereoselective total synthesis of a potent natural antifungal compound (6S)-5,6,dihydro-6-[(2R)-2-hydroxy-6-phenyl hexyl]-2H-pyran-2-one
    Das, Biswanath
    Laxminarayana, Keetha
    Krishnaiah, Martha
    Kumar, Duddukuri Nandan
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (22) : 6396 - 6398
  • [33] Multistep synthesis of the biocompatible lactone 3,6-dihydro-2H-pyran-2-one
    Cundiff, Brad
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [34] PHOTOCHEMICAL SYNTHESES OF DESOXIDE, NEROL OXIDE AND 2,2,6-TRIMETHYL-6-VINYL-5,6-DIHYDRO-2H-PYRAN
    吴国生
    马云飞
    葛明娟
    李尊良
    刘铸晋
    ChineseScienceBulletin, 1989, (04) : 305 - 308
  • [35] PHOTOCHEMICAL SYNTHESES OF DESOXIDE, NEROL OXIDE AND 2,2,6-TRIMETHYL-6-VINYL-5,6-DIHYDRO-2H-PYRAN
    WU, GS
    MA, YF
    GE, MJ
    LI, ZL
    LIU, ZJ
    CHINESE SCIENCE BULLETIN, 1989, 34 (04): : 305 - 308
  • [36] REACTION OF 2-BUTYNOIC ACID DIANION WITH ALDEHYDES - SYNTHESIS OF SOME NATURAL-PRODUCTS WITH 5,6-DIHYDRO-2H-PYRAN-2-ONE STRUCTURE
    MEYER, HH
    JUSTUS LIEBIGS ANNALEN DER CHEMIE, 1978, (02): : 327 - 344
  • [37] Identification of 5,6-dihydro-6-propyl-2H-pyran-2-one as the major volatile constituent in mesquite (Prosopis) flour
    Takeoka, Gary R.
    Wong, Rosalind Y.
    Dao, Lan
    Felker, Peter
    FOOD CHEMISTRY, 2009, 115 (03) : 1025 - 1027
  • [38] DERIVATIVES OF 5,6-DIHYDRO-2H-PYRAN-3-CARBOXYLIC ACID
    SPREITZER, H
    MULLER, P
    BUCHBAUER, G
    MONATSHEFTE FUR CHEMIE, 1990, 121 (11): : 963 - 970
  • [39] STRUCTURE OF 5,6-DIHYDRO-2H-PYRAN
    KRAJEWSKI, JW
    URBANCZYKLIPKOWSKA, Z
    GLUZINSKI, P
    ACTA CRYSTALLOGRAPHICA SECTION A, 1978, 34 : S85 - S85
  • [40] SYNTHESIS OF 6-(2-PHENYLETHENYL)-2H-PYRAN-2-ONE
    TOMINAGA, Y
    USHIROGOCHI, A
    MATSUDA, Y
    KOBAYASHI, G
    HETEROCYCLES, 1977, 8 : 193 - 197
12345