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

View/ Open
Issue Date
2018-11-01Author
Aksenov, Nicolai A.
Aksenov, Alexander V.
Kornienko, Alexander
De Carvalho, Annelise
Mathieu, Véronique
Aksenov, Dmitrii A.
Ovcharov, Sergei N.
Griaznov, Georgii D.
Rubin, Michael
Publisher
Royal Society of Chemistry
Type
Article
Article Version
Scholarly/refereed, publisher version
Rights
This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported License. © The Royal Society of Chemistry 2018.
Metadata
Show full item recordAbstract
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.
Collections
Citation
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.
Items in KU ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.
We want to hear from you! Please share your stories about how Open Access to this item benefits YOU.