Synthesis of imidazo[1,5,4-de]quinoxalin-9-ones, benzimidazole analogues of pyrroloiminoquinone marine natural products

被引：38

作者：

LaBarbera, DV ^{[1
]}

Skibo, EB ^{[1
]}

机构：

[1] Arizona State Univ, Dept Chem & Biochem, Tempe, AZ 85287 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2005年 / 13卷 / 02期

基金：

美国国家科学基金会;

关键词：

imidazoquinoxalinones; benzimidazole; pyrroloiminoquinone;

D O I：

10.1016/j.bmc.2004.10.016

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The imidazoquinoxalinones 1 and 2 are benzimidazole analogues of indole-based marine natural products called makaluvamins. The stabilized cation 1 and the zwitterion 2 were prepared in similar to9 steps from readily available starting materials. Compound 1 is more cytostatic and cytotoxic than 2 and also shows activity in the hollow fiber assay. Unlike the indole-based natural products, 1 and 2 are not potent topoisomerase II inhibitors. Their pattern of cytotoxic and cyostatic activity could be related to inhibition of protein tyrosine kinases. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：387 / 395

页数：9

共 21 条

[1] EFFECT OF SUBSTITUENTS IN THE FORMATION OF DIACETANILIDES [J].

AYYANGAR, NR ;

SRINIVASAN, KV .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (07) :1292-1296

[2]

BARROWS LR, 1993, ANTI-CANCER DRUG DES, V8, P333

[3]

BOYD MR, 1989, PRINCIPLES PRACTICE, P1

[4] WAKAYIN - A NOVEL CYTOTOXIC PYRROLOIMINOQUINONE ALKALOID FROM THE ASCIDIAN CLAVELINA SPECIES [J].

COPP, BR ;

IRELAND, CM ;

BARROWS, LR .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) :4596-4597

[5]

GRISWOLD DP, 1972, CANCER CHEMOTH REP 2, V3, P315

[6]

HALL IH, 1992, ANTICANCER RES, V12, P1355

[7] SYNTHESIS AND PHYSICAL STUDIES OF AZAMITOSENE AND IMINOAZAMITOSENE REDUCTIVE ALKYLATING-AGENTS - IMINOQUINONE HYDROLYTIC STABILITY, SYN/ANTI-ISOMERIZATION, AND ELECTROCHEMISTRY [J].

ISLAM, I ;

SKIBO, EB .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3195-3205

[8] Synthetic routes to pyrroloiminoquinone alkaloids. A direct synthesis of makaluvamine C [J].

Kraus, GA ;

Selvakumar, N .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9846-9849

[9] Quantitative structure-activity relationship of flavonoid analogues.: 3.: Inhibition of p56lck protein tyrosine kinase [J].

Oblak, M ;

Randic, M ;

Solmajer, T .

JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, 2000, 40 (04) :994-1001

[10] DISPLAY AND ANALYSIS OF PATTERNS OF DIFFERENTIAL ACTIVITY OF DRUGS AGAINST HUMAN-TUMOR CELL-LINES - DEVELOPMENT OF MEAN GRAPH AND COMPARE ALGORITHM [J].

PAULL, KD ;

SHOEMAKER, RH ;

HODES, L ;

MONKS, A ;

SCUDIERO, DA ;

RUBINSTEIN, L ;

PLOWMAN, J ;

BOYD, MR .

JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1989, 81 (14) :1088-1092

← 1 2 3 →