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Molecules 2018, 23(9), 2155; https://doi.org/10.3390/molecules23092155

Synthesis, Bacteriostatic and Anticancer Activity of Novel Phenanthridines Structurally Similar to Benzo[c]phenanthridine Alkaloids

1
Department of Organic Chemistry, Faculty of Science, Palacký University, 17. Listopadu 1192/12, CZ-771 46 Olomouc, Czech Republic
2
Institute of Molecular and Translation Medicine, Faculty of Medicine, Palacký University, Hněvotínská 5, CZ-779 00 Olomouc, Czech Republic
3
Laboratory of Growth Regulators, Faculty of Science, Palacký University and Institute of Experimental Botany ASCR, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic
*
Author to whom correspondence should be addressed.
Received: 31 July 2018 / Revised: 23 August 2018 / Accepted: 24 August 2018 / Published: 27 August 2018
(This article belongs to the Special Issue Heterocycles in Medicinal Chemistry)
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Abstract

In this study, we report the synthesis, antibacterial and anticancer evaluation of 38 novel phenanthridines that were designed as analogs of the benzo[c]phenanthridine alkaloids. The prepared phenanthridines differ from the benzo[c]phenanthridines in the absence of a benzene A-ring. All novel compounds were prepared from 6-bromo-2-hydroxy-3-methoxybenzaldehyde in several synthetic steps through reduction of Schiff bases and accomplished by radical cyclization. Twelve derivatives showed high antibacterial activity against Bacillus subtilis, Micrococcus luteus and/or Mycobacterium vaccae at single digit micromolar concentrations. Some compounds also displayed cytotoxicity against the K-562 and MCF-7 cancer cell lines at as low as single digit micromolar concentrations and were more potent than chelerythrine and sanguinarine. The active compounds caused cell-cycle arrest in cancer cells, increased levels of p53 protein and caused apoptosis-specific fragmentation of PARP-1. Biological activity was connected especially with the presence of the N-methyl quaternary nitrogen and 7-benzyloxy substitution (compounds 7i, 7j, 7k, and 7l) of phenanthridine. View Full-Text
Keywords: phenanthridines; benzo[c]phenanthridines; radical cyclization; antiproliferative; antibacterial activity phenanthridines; benzo[c]phenanthridines; radical cyclization; antiproliferative; antibacterial activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Lasák, P.; Motyka, K.; Kryštof, V.; Stýskala, J. Synthesis, Bacteriostatic and Anticancer Activity of Novel Phenanthridines Structurally Similar to Benzo[c]phenanthridine Alkaloids. Molecules 2018, 23, 2155.

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