A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities
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2018-11-01Article Version
Scholarly/refereed, publisher version
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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.
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Aksenov NA, Aksenov AV, Kornienko A, De Carvalho A, Mathieu V, Aksenov DA, Ovcharov SN, Griaznov GD, Rubin M. A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities. RSC Adv. 2018 Nov 1;8(64):36980-36986. doi: 10.1039/c8ra08155g. PMID: 35558925; PMCID: PMC9089289.
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