A cascade synthetic route to new bioactive spiroindolinepyrido[1,2-a]indolediones from indirubin

作者: Alexander M. Sele , John B. Bremner , Anthony C. Willis , Rachada Haritakun , Renate Griffith

DOI: 10.1016/J.TET.2015.08.012

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摘要: Abstract The allylation of indirubin produced the expected indolic N′-allylindirubin and N,N′-diallylindirubin derivatives in moderate yields, together with corresponding N-substituted isatin products. At higher temperatures, base-initiated reaction allylic halides yielded spiroindolinepyrido[1,2-a]indolediones a one-pot cascade sequence yields up to 70%. These readily accessed, new spiro compounds represent first reported examples participating reactions. Preliminary in vitro biological testing some products indicated promising activity against cancer cell lines Plasmodium falciparum for two derivatives. Computational methods were used gain greater understanding UV/Vis spectroscopic data N′-substituted N,N′-disubstituted

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