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

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

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

RSC Adv., 2018,8, 36980-36986

Permissions

Request permissions

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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements