Montmorillonite K-10 catalyzed cyclization of N-ethoxycarbonyl-N′-arylguanidines: Access to pyrimido[4,5-c]carbazole and pyrimido[5,4-b]indole derivatives

被引：18

作者：

Debray, Julien ^{[1
,2
]}

Zeghida, Walid ^{[1
,2
]}

Baldeyrou, Brigitte ^{[3
,4
]}

Mahieu, Christine ^{[3
,4
]}

Lansiaux, Amelie ^{[3
,4
]}

Demeunynck, Martine ^{[1
,2
]}

机构：

[1] Univ Grenoble 1, CNRS, Dept Chim Mol, UMR 5250, F-38041 Grenoble 9, France

[2] Univ Grenoble 1, CNRS, ICMG, FR 2607, F-38041 Grenoble 9, France

[3] Univ Nord France, Ctr Oscar Lambret, INSERM, IMPRT,U837, F-59045 Lille, France

[4] Inst Rech Canc Lille, F-59045 Lille, France

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2010年 / 20卷 / 14期

关键词：

Nitrogen heterocycles; Carbazole; Indole; Friedel-Crafts; DNA binding; Topoisomerase; ANTITUMOR-ACTIVITY; CARBAZOLES; SERIES;

D O I：

10.1016/j.bmcl.2010.05.028

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Two new heterocycles, pyrimido[4,5-c]carbazole and pyrimido[5,4-b]indole, were prepared in three steps from 3-aminocarbazole and 3-aminoindole, respectively. The key Friedel-Crafts intramolecular cyclization was realized under microwave irradiation using montmorillonite K-10 clay as a catalyst. The pyrimido[4,5-c]carbazole derivative shows significant micromolar IC(50) against cancer cell lines. Unlike similar carbazole and indolocarbazole compounds, the molecule does not interfere with topoisomerase activity. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：4244 / 4247

页数：4

共 13 条

[11] A new and efficient catalytic method for synthesizing isocyanates from carbamates [J].