Structure-activity relationships of phomactin derivatives as platelet activating factor antagonists

被引:37
作者
Sugano, M
Sato, A
Saito, K
Takaishi, S
Matsushita, Y
Iijima, Y
机构
[1] SANKYO CO LTD,BIOMED RES LABS,SHINAGAWA KU,TOKYO 140,JAPAN
[2] SANKYO CO LTD,PHARMACOL & MOL BIOL RES LABS,SHINAGAWA KU,TOKYO 140,JAPAN
关键词
D O I
10.1021/jm950640q
中图分类号
R914 [药物化学];
学科分类号
100701 [药物化学];
摘要
Phomactins, natural products isolated from the culture broth of marine fungus Phoma sp., were found to be active as PAF antagonists. This unique carbon skeleton led us to investigate the structure-activity relationship demonstrating that the lipophilicity at C-(7-8), acetoxy, (methoxycarbonyl)oxy, and S-isoxazolyloxy substitution at C-20, and 2-beta-OH configuration at C-2 are all required for the enhancement of inhibitor activity.
引用
收藏
页码:5281 / 5284
页数:4
相关论文
共 13 条
[1]
CONFORMATION AND ACTIVITY OF TETRAHYDROFURAN LIGNANS AND ANALOGS AS SPECIFIC PLATELET-ACTIVATING-FACTOR ANTAGONISTS [J].
BIFTU, T ;
GAMBLE, NF ;
DOEBBER, T ;
HWANG, SB ;
SHEN, TY ;
SNYDER, J ;
SPRINGER, JP ;
STEVENSON, R .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (10) :1917-1921
[2]
BRACQUET P, 1987, PHARM REW, V39, P97
[3]
CASALSSTENZEL J, 1987, J PHARMACOL EXP THER, V241, P974
[4]
DEMOPOULOS CA, 1979, J BIOL CHEM, V254, P9355
[5]
ACTIVATION OF GUINEA-PIG PERITONEAL-MACROPHAGES BY PLATELET ACTIVATING FACTOR (PAF) AND ITS AGONISTS [J].
HAYASHI, H ;
KUDO, I ;
INOUE, K ;
ONOZAKI, K ;
TSUSHIMA, S ;
NOMURA, H ;
NOJIMA, S .
JOURNAL OF BIOCHEMISTRY, 1985, 97 (06) :1737-1745
[6]
AN EFFICIENT SYNTHESIS OF PLATELET-ACTIVATING FACTOR (PAF) VIA 1-0-ALKYL-2-O-(3-ISOXAZOLYL)-SN-GLYCERO-3-PHOSPHOCHOLINE, A NEW PAF AGONIST - UTILIZATION OF THE 3-ISOXAZOLYLOXY GROUP AS A PROTECTED HYDROXYL [J].
NAKAMURA, N ;
MIYAZAKI, H ;
OHKAWA, N ;
OSHIMA, T ;
KOIKE, H .
TETRAHEDRON LETTERS, 1990, 31 (05) :699-702
[7]
SYNTHESIS AND BIOLOGICAL-ACTIVITY OF MK-287 (L-680,573) - A POTENT, SPECIFIC AND ORALLY ACTIVE PAF RECEPTOR ANTAGONIST [J].
SAHOO, SP ;
GRAHAM, DW ;
ACTON, J ;
BIFTU, T ;
BUGIANESI, RL ;
GIROTRA, NN ;
KUO, CH ;
PONPIPOM, MM ;
DOEBBER, TW ;
WU, MS ;
HWANG, SB ;
LAM, MH ;
MACINTYRE, DE ;
BACH, TJ ;
LUELL, S ;
MEURER, R ;
DAVIES, P ;
ALBERTS, AW ;
CHABALA, JC .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (06) :327-332
[8]
PHOMACTIN-E, PHOMACTIN-F, AND PHOMACTIN-G - NEW PHOMACTIN-GROUP PAF ANTAGONISTS FROM A MARINE FUNGUS PHOMA SP [J].
SUGANO, M ;
SATO, A ;
IIJIMA, Y ;
FURUYA, K ;
KUWANO, H ;
HATA, T .
JOURNAL OF ANTIBIOTICS, 1995, 48 (10) :1188-1190
[9]
PHOMACTINS, NOVEL PAF ANTAGONISTS FROM MARINE FUNGUS PHOMA SP [J].
SUGANO, M ;
SATO, A ;
IIJIMA, Y ;
FURUYA, K ;
HARUYAMA, H ;
YODA, K ;
HATA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (03) :564-569
[10]
PHOMACTIN-A - A NOVEL PAF ANTAGONIST FROM A MARINE FUNGUS PHOMA SP [J].
SUGANO, M ;
SATO, A ;
IIJIMA, Y ;
OSHIMA, T ;
FURUYA, K ;
KUWANO, H ;
HATA, T ;
HANZAWA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) :5463-5464