Issue 64, 2018
From the journal:

RSC Advances

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

Nicolai A. Aksenov, ORCID logo *a   Alexander V. Aksenov, ORCID logo a   Alexander Kornienko, ORCID logo b   Annelise De Carvalho,cd   Véronique Mathieu,cd   Dmitrii A. Aksenov,a   Sergei N. Ovcharov,a   Georgii D. Griaznove  and  Michael Rubin ORCID logo *ae  

* Corresponding authors

a Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355009, Russian Federation
E-mail: naksenov@ncfu.ru

b Department of Chemistry and Biochemistry, Texas State University, San Marcos, Texas 78666, USA

c Department of Pharmacotherapy and Pharmaceutics, Faculté de Pharmacie, Université Libre de Bruxelles, Brussels, Belgium

d ULB Cancer Research Center, Université Libre de Bruxelles, Brussels, Belgium

e Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr., Lawrence, KS 66045-7582, USA
E-mail: mrubin@ku.edu
Tel: +1-785-864-5071

Abstract

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.

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

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Article information

DOI
https://doi.org/10.1039/C8RA08155G
Article type
Paper
Submitted
01 out 2018
Accepted
23 out 2018
First published
01 nov 2018
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2018,8, 36980-36986

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

N. A. Aksenov, Alexander V. Aksenov, A. Kornienko, A. De Carvalho, V. Mathieu, D. A. Aksenov, S. N. Ovcharov, G. D. Griaznov and M. Rubin, RSC Adv., 2018, 8, 36980 DOI: 10.1039/C8RA08155G

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