One-Pot Synthesis of Functionalized [6-5-6-6-3] Heteropentacyclic Indolo[3,2,1-de][1,5]naphthyridine-Fused Scaffold
Jiao Yuan1,2, Dong-Qun Huang1,2, Lei Yang2
1College of Food and Biological Engineering, Chengdu University, Chengdu 610106, China.
Abstract:
Herein, we develop a simple and straightforward method to access a [6-5-6-6-3] heteropentacyclic indolo[3,2,1-de][1,5]naphthyridine-fused scaffold through multistep cascade reactions involving α-aryl vinylsulfoniums. Under mild reaction conditions, the reaction is applicable to β-carboline-based chalcones and 1-carbonyl-9H-β-carbolines, delivering the indolo[3,2,1-de][1,5]naphthyridine-fused cyclopropane and oxiranes in moderate to excellent isolated yields. In addition, the scale-up synthesis, derivatizations of products, and late-stage functionalization of bioactive molecules also demonstrated the potential utility of this method. Particularly, a preliminary biological evaluation exhibited moderate to good cytotoxicity in vitro against multiple types of tumor cells.
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