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Issue 11, 2016
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Synthesis and antiproliferative activity of novel hybrid 3-substituted polyhydroquinoline-fatty acids

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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

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Supplementary files

Article information


Submitted
27 Jul 2016
Accepted
25 Aug 2016
First published
30 Aug 2016

Med. Chem. Commun., 2016,7, 2167-2176
Article type
Research Article

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

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