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A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities

par Aksenov, Nicolai N.A.;Aksenov, Alexander A.V.;Kornienko, Alexander;De Carvalho, Annelise;Mathieu, Véronique ;Aksenov, Dmitrii D.A.;Ovcharov, Sergei S.N.;Griaznov, Georgii G.D.;Rubin, Michael
Référence RSC advances, 8, 64, page (36980-36986)
Publication Publié, 2018

Article révisé par les pairs

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Résumé :

A second generation polyphosphoric acid-mediated one-pot three-component synthesis of indoloquinoline scaffold is developed. This improved version of the process involves electrophilically activated nitroalkanes for the installation of strategic C-C and C-N bonds and ring C assembly. This modification allows the elimination of unnecessary solvent change operations and all steps are carried out in a true, uninterrupted one-pot manner. A further improvement involves the possibility to install an ortho-amino group in situ. A synthetic application of this method is showcased by the concise synthesis of an isocryptolepine alkaloid and its synthetic analogs with potent anticancer activities.