STRUCTURE-ACTIVITY RELATIONSHIP OF ALPHA-GALACTOSYLCERAMIDES AGAINST B16-BEARING MICE

被引：510

作者：

MORITA, M ^{[1
]}

MOTOKI, K ^{[1
]}

AKIMOTO, K ^{[1
]}

NATORI, T ^{[1
]}

SAKAI, T ^{[1
]}

SAWA, E ^{[1
]}

YAMAJI, K ^{[1
]}

KOEZUKA, Y ^{[1
]}

KOBAYASHI, E ^{[1
]}

FUKUSHIMA, H ^{[1
]}

机构：

[1] KIRIN BREWERY CO LTD,PHARMACEUT RES LAB,TAKASAKI,GUMMA 37012,JAPAN

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1995年 / 38卷 / 12期

关键词：

D O I：

10.1021/jm00012a018

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Agelasphin-9b, (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-16-methyl-2-[N-((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S;4R)-1-O-(alpha-D-galactopyranosyl)2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.

引用

页码：2176 / 2187

页数：12

共 39 条

[1] SYNTHESIS AND STEREOCHEMISTRY OF AGELASPHIN-9B [J].

AKIMOTO, K ;

NATORI, T ;

MORITA, M .

TETRAHEDRON LETTERS, 1993, 34 (35) :5593-5596

[2] GALACTOSYL CERAMIDE OR A DERIVATIVE IS AN ESSENTIAL COMPONENT OF THE NEURAL RECEPTOR FOR HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 ENVELOPE GLYCOPROTEIN GP120 [J].

BHAT, S ;

SPITALNIK, SL ;

GONZALEZSCARANO, F ;

SILBERBERG, DH .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (16) :7131-7134

[3]

CLARK JW, 1986, MEDIGUIDE ONCOLOGY, V6, P1

[4] STEREOCHEMISTRY ASSOCIATED WITH THE ADDITION OF 2-(TRIMETHYLSILYL)THIAZOLE TO DIFFERENTIALLY PROTECTED ALPHA-AMINO ALDEHYDES - APPLICATIONS TOWARD THE SYNTHESIS OF AMINO-SUGARS AND SPHINGOSINES [J].

DONDONI, A ;

FANTIN, G ;

FOGAGNOLO, M ;

PEDRINI, P .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1439-1446

[5]

DYATKINA NB, 1984, SYNTHESIS-STUTTGART, P961

[6] A SYNTHESIS OF PHYTOSPHINGOSINES FROM D-GALACTOSE [J].

GIGG, J ;

GIGG, R .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (20) :1876-&

[7] A SYNTHESIS OF PHYTOSPINGOSINES FORM D-GLUCOSAMINE [J].

GIGG, J ;

GIGG, R ;

WARREN, CD .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (20) :1872-+

[8] ASYMMETRIC-SYNTHESIS VIA HETEROCYCLIC INTERMEDIATES .43. ASYMMETRIC-SYNTHESIS OF D-ERYTHRO-SPHINGOSINE [J].

GROTH, U ;

SCHOLLKOPF, U ;

TILLER, T .

TETRAHEDRON, 1991, 47 (16-17) :2835-2842

[9] STEREOSELECTIVE PREPARATION OF SYNTHETIC EQUIVALENTS OF 2-DEOXY-2-AMINO-AMINOTETROSES AND 3-DEOXY-3-AMINOTETROSES FROM MALIC-ACID - APPLICATION TO THE SYNTHESIS OF C18-D-RIBO-PHYTOSPHINGOSINE [J].

GUANTI, G ;

BANFI, L ;

NARISANO, E .

TETRAHEDRON LETTERS, 1989, 30 (40) :5507-5510

[10]

HAKOMORI SI, 1990, J BIOL CHEM, V265, P18713

← 1 2 3 4 →