Synthesis and antiproliferative activities of isoindigo and azaisoindigo derivatives

被引：54

作者：

Bouchikhi, Fadoua ^{[1
]}

Anizon, Fabrice ^{[1
]}

Moreau, Pascale ^{[1
]}

机构：

[1] Univ Blaise Pascal, Lab SEESIB, CNRS, UMR 6504, F-63177 Aubiere, France

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2008年 / 43卷 / 04期

关键词：

indigoids; isoindigos; 7'-azaisoindigo; in vitro antiproliferative activities;

D O I：

10.1016/j.ejmech.2007.05.012

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

In the course of structure-activity relationship studies, diversely substituted 1-(beta-D-acetylatedglucopyranosyl)isoindigoderivatives were prepared from indolines. New 7'-azaisoindigo analogues were also synthesized by coupling a glycosylated isatine and a 7-azaindolin-2-one derivative. Compounds containing a 7'-azaisoindigo framework have never been described before. To get an insight into the substitution pattern required for the best biological potencies, their antiproliferative activities were evaluated toward a human buccal carcinoma cell line (KB) and two human myeloid leukaemia cell lines (K562, HL60). (c) 2007 Elsevier Masson SAS. All rights reserved.

引用

页码：755 / 762

页数：8

共 11 条

[1] Design and synthesis of aminopropyl tetrahydroindole-based indolin-2-ones as selective and potent inhibitors of Src and Yes tyrosine kinase [J].

Guan, HP ;

Laird, AD ;

Blake, RA ;

Tang, C ;

Liang, C .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (01) :187-190

[2] REGIOSELECTIVE SYNTHESIS OF ACYLPYRROLES [J].

KAKUSHIMA, M ;

HAMEL, P ;

FRENETTE, R ;

ROKACH, J .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (19) :3214-3219

[3] OXIDATION OF INDOLES WITH PYRIDINIUM BROMIDE PERBROMIDE A SIMPLE AND EFFICIENT SYNTHESIS OF 7-AZAOXINDOLES [J].

MARFAT, A ;

CARTA, MP .

TETRAHEDRON LETTERS, 1987, 28 (35) :4027-4030

[4]

Mazéas D, 1999, HETEROCYCLES, V50, P1065

[5] 7-AZAINDOLE .5. INVESTIGATIONS OF ALTERNATIVE SYNTHESES OF THE RING SYSTEM [J].

OKUDA, S ;

ROBISON, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (03) :740-743

[6] Concise syntheses of the cruciferous phytoalexins brassilexin, sinalexin, wasalexins, and analogues: Expanding the scope of the Vilsmeier formylation [J].

Pedras, MSC ;

Jha, M .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (05) :1828-1834

[7] Synthesis and antiproliferative activities of diversely substituted glycosyl-isoindigo derivatives [J].

Sassatelli, M ;

Bouchikhi, F ;

Messaoudi, S ;

Anizon, F ;

Debiton, E ;

Barthomeuf, C ;

Prudhomme, M ;

Moreau, P .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (01) :88-100

[8] Synthesis of glycosyl-isoindigo derivatives [J].

Sassatelli, M ;

Saab, E ;

Anizon, F ;

Prudhomme, M ;

Moreau, P .

TETRAHEDRON LETTERS, 2004, 45 (25) :4827-4830

[9] STRUCTURE-ACTIVITY-RELATIONSHIPS IN THE 8-AMINO-6,7,8,9-TETRAHYDRO-3H-BENZ[E]INDOLE RING-SYSTEM .1. EFFECTS OF SUBSTITUENTS IN THE AROMATIC SYSTEM ON SEROTONIN AND DOPAMINE-RECEPTOR SUBTYPES [J].

STJERNLOF, P ;

ENNIS, MD ;

HANSSON, LO ;

HOFFMAN, RL ;

GHAZAL, NB ;

SUNDELL, S ;

SMITH, MW ;

SVENSSON, K ;

CARLSSON, A ;

WIKSTROM, H .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (12) :2202-2216

[10] Synthesis and biological evaluations of 3-substituted indolin-2-ones: A novel class of tyrosine kinase inhibitors that exhibit selectivity toward particular receptor tyrosine kinases [J].

Sun, L ;

Tran, N ;

Tang, F ;

App, H ;

Hirth, P ;

McMahon, G ;

Tang, C .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (14) :2588-2603

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