Issue 11, 2016

Synthesis and antiproliferative activity of novel hybrid 3-substituted polyhydroquinoline-fatty acids

Abstract

This work describes the synthesis of new long-chain fatty acid polyhydroquinoline derivatives (hybrid PHQ-fatty acids) using a Hantzsch four-component reaction without the use of metals and catalyzed by non-toxic acids. The PHQ-fatty acids were synthesized from fatty β-ketoesters in the presence of sulfamic acid (H2NSO3H) in good yields (70–81%). Following the synthesis, for the first time, the in vitro antiproliferative activity of a series of long-chain PHQ-fatty acids was investigated in a glioma cell line (C6 rat malignant GBM cell line). Notably, all of the tested compounds were active against this cell line. Superior activity was observed for PHQ with a hydroxyl group on the aromatic ring and a stearic fatty acid chain, reducing the cell viability by ca. 40% at 5 μM.

Graphical abstract: Synthesis and antiproliferative activity of novel hybrid 3-substituted polyhydroquinoline-fatty acids

Supplementary files

Article information

Article type
Research Article
Submitted
27 Jul 2016
Accepted
25 Aug 2016
First published
30 Aug 2016

Med. Chem. Commun., 2016,7, 2167-2176

Synthesis and antiproliferative activity of novel hybrid 3-substituted polyhydroquinoline-fatty acids

D. da Costa Cabrera, S. B. Rosa, F. S. de Oliveira, M. A. G. Marinho, C. R. Montes D'Oca, D. Russowsky, A. P. Horn and M. G. Montes D'Oca, Med. Chem. Commun., 2016, 7, 2167 DOI: 10.1039/C6MD00425C

To request permission to reproduce material from this article, 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 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.

Spotlight

Advertisements