Synthesis and biological activity of new quinoxaline antibiotics of echinomycin analogues

被引:287
作者
Kim, YB
Kim, YH [1 ]
Park, JY
Kim, SK
机构
[1] Korea Adv Inst Sci & Technol, Ctr Mol Design & Synth, Dept Chem, Taejon 305701, South Korea
[2] Yonsei Univ, Dept Microbiol, Wonju Coll Med, Inst Basic Med Sci,IFBB, Wonju 220701, South Korea
关键词
echinomycin; anticancer; active-VRE; apoptosis;
D O I
10.1016/j.bmcl.2003.09.086
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Novel quinoxaline antibiotics having the methylenedithioether bridge as an analogue of echinomycin have been synthesized by insertion of methylene moiety between -S-S- bond. The compound la shows remarkable cytotoxicities against human tumor various cell lines, and is active VRE (vancomycin-resistant enterococci) within MIC range 0.5-8 mug/mL. According to the eukaryotic or prokaryotic data, la might be a first analogue to replace echinomycin. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:541 / 544
页数:4
相关论文
共 33 条
[1]   Development of a solution-phase synthesis of minor groove binding bis-intercalators based on triostin A suitable for combinatorial synthesis [J].
Boger, DL ;
Lee, JK .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :5996-6000
[2]   Total syntheses of thiocoraline and BE-22179: Establishment of relative and absolute stereochemistry [J].
Boger, DL ;
Ichikawa, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (12) :2956-2957
[3]   BENZAMIDOMETHYL GROUP AS A THIOL PROTECTING GROUP FOR CYSTEINE, N-METHYLCYSTEINE, AND CORRESPONDING N-TERT-BUTYLOXYCARBONYL DERIVATIVES [J].
CHAKRAVARTY, PK ;
OLSEN, RK .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (06) :1270-1271
[4]  
CHAKRAVARTY PK, 1978, TETRAHEDRON LETT, V19, P1613
[5]  
CHEUNG ST, 1977, CAN J CHEM, V55, P2987
[6]  
CHEW WY, 1975, J ORG CHEM, V40, P3110
[7]   SYNTHESIS OF DES-N-TETRAMETHYLTRIOSTIN-A, A BICYCLIC OCTADEPSIPEPTIDE RELATED TO QUINOXALINE ANTIBIOTICS [J].
CIARDELLI, TL ;
OLSEN, RK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (08) :2806-2807
[8]   DES-N-TETRAMETHYLTRIOSTIN-A AND BIS-L-SERYLDES-N-TETRAMETHYLTRIOSTIN-A, SYNTHETIC ANALOGS OF QUINOXALINE ANTIBIOTICS [J].
CIARDELLI, TL ;
CHAKRAVARTY, PK ;
OLSEN, RK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (24) :7684-7690
[9]  
COREY EJ, 1977, TETRAHEDRON LETT, V18, P3919
[10]   SYNTHESIS OF DES-N-TETRAMETHYLTRIOSTIN A FROM C-TERMINAL Z-D-SERINE TETRADEPSIPEPTIDE AND OCTADEPSIPEPTIDE INTERMEDIATES [J].
DHAON, MK ;
GARDNER, JH ;
OLSEN, RK .
TETRAHEDRON, 1982, 38 (01) :57-61