PH-DEPENDENT STABILITY AND REACTIVITY OF A THIOL-QUINONE METHIDE ADDUCT

被引：8

作者：

ANGLE, SR

YANG, WJ

机构：

[1] Department of Chemistry, University of California, Riverside

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 41期

基金：

美国国家卫生研究院;

关键词：

QUINONE METHIDES; ANTHRACYCLINE ANTITUMOR ANTIBIOTICS; PH DEPENDENT;

D O I：

10.1016/S0040-4039(00)60013-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

10-Acetyl-1-(butanethio)-1,2,3,4-tetrahydro-9,10-anthracenediol 2a, a quinone methide-butane-thiol adduct has been prepared in 63% yield. The pH-dependent stability and reaction with 2'-deoxyadenosine showed that the nucleoside can be exchanged for the thiol at pH 7.

引用

页码：6089 / 6092

页数：4

共 20 条

[1] A CHEMICAL PERSPECTIVE ON THE ANTHRACYCLINE ANTITUMOR ANTIBIOTICS
ABDELLA, BRJ
FISHER, J
[J]. ENVIRONMENTAL HEALTH PERSPECTIVES, 1985, 64 : 3 - 18
[2] NUCLEOPHILIC-ADDITION OF 2'-DEOXYNUCLEOSIDES TO THE ORTHO-QUINONE METHIDES 10-(ACETYLOXY) AND 10-METHOXY-3,4-DIHYDRO-9(2H)-ANTHRACENONE
ANGLE, SR
YANG, WJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) : 1092 - 1097
[3] SYNTHESIS AND CHEMISTRY OF A QUINONE METHIDE MODEL FOR ANTHRACYCLINE ANTITUMOR ANTIBIOTICS
ANGLE, SR
YANG, WJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) : 4524 - 4528
[4] ANNE A, 1985, NOUV J CHIM, V9, P83
[5] FORMATION AND AUTOCATALYTIC DESTRUCTION OF THE QUINONE METHIDE FROM REDUCTIVE CLEAVAGE OF MENOGARIL
BOLDT, M
GAUDIANO, G
HADDADIN, MJ
KOCH, TH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (10) : 3330 - 3332
[6] FORMATION AND REACTION OF THE QUINONE METHIDE FROM REDUCTIVE CLEAVAGE OF THE ANTITUMOR DRUG MENOGARIL
BOLDT, M
GAUDIANO, G
HADDADIN, MJ
KOCH, TH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (06) : 2283 - 2292
[7] COUPLING OF THE ANTHRACYCLINE ANTITUMOR DRUG MENOGARIL TO 2'-DEOXYGUANOSINE THROUGH REDUCTIVE ACTIVATION
EGHOLM, M
KOCH, TH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) : 8291 - 8293
[8] ANTHRACYCLINE ANTIBIOTIC REDUCTION BY SPINACH FERREDOXIN NADP+ REDUCTASE AND FERREDOXIN
FISHER, J
ABDELLA, BRJ
MCLANE, KE
[J]. BIOCHEMISTRY, 1985, 24 (14) : 3562 - 3571
[9] Fisher J F, 1988, Prog Drug Res, V32, P411
[10] SPECTROSCOPIC AND KINETIC EVIDENCE FOR THE TAUTOMER OF 7-DEOXYALKLAVINONE AS AN INTERMEDIATE IN THE REDUCTIVE COUPLING OF ACLACINOMYCIN-A
KLEYER, DL
GAUDIANO, G
KOCH, TH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (04) : 1105 - 1109

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