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

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• 作者：Julien Debray ; Walid Zeghida ; Brigitte Baldeyrou ; Christine Mahieu ; Amé ; lie Lansiaux ; Martine Demeunynck
• 关键词：Nitrogen heterocycles ; Carbazole ; Indole ; Friedel– ; Crafts ; DNA binding ; Topoisomerase
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2010
• 出版时间：15 July 2010
• 年：2010
• 卷：20
• 期：14
• 页码：4244-4247
• 全文大小：405 K

文摘

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 IC₅₀ against cancer cell lines. Unlike similar carbazole and indolocarbazole compounds, the molecule does not interfere with topoisomerase activity.