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Molecules 2014, 19(12), 19435-19459; doi:10.3390/molecules191219435

Synthesis, Anticancer and Antibacterial Activity of Salinomycin N-Benzyl Amides

1
Faculty of Chemistry, Adam Mickiewicz University, Umultowska 89 b, 61-614 Poznań, Poland
2
Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Rudolfa Weigla 12, 53-114 Wrocław, Poland
3
Department of Microbiology, Institute of Tuberculosis and Pulmonary Diseases, Płocka 26, 01-138 Warsaw, Poland
4
Department of Pharmaceutical Microbiology, University of Warsaw, Oczki 3, 02-007 Warsaw, Poland
5
Institute of Low Temperature and Structure Research, Polish Academy of Sciences, P.O. Box 1410, 50-950 Wrocław, Poland
*
Author to whom correspondence should be addressed.
Received: 14 October 2014 / Revised: 13 November 2014 / Accepted: 14 November 2014 / Published: 25 November 2014
(This article belongs to the Collection Bioactive Compounds)
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Abstract

A series of 12 novel monosubstituted N-benzyl amides of salinomycin (SAL) was synthesized for the first time and characterized by NMR and FT-IR spectroscopic methods. Molecular structures of three salinomycin derivatives in the solid state were determined using single crystal X-ray method. All compounds obtained were screened for their antiproliferative activity against various human cancer cell lines as well as against the most problematic bacteria strains such as methicillin-resistant Staphylococcus aureus (MRSA) and Staphylococcus epidermidis (MRSE), and Mycobacterium tuberculosis. Novel salinomycin derivatives exhibited potent anticancer activity against drug-resistant cell lines. Additionally, two N-benzyl amides of salinomycin revealed interesting antibacterial activity. The most active were N-benzyl amides of SAL substituted at -ortho position and the least anticancer active derivatives were those substituted at the -para position. View Full-Text
Keywords: anticancer activity; antibacterial activity; antitubercular activity; SAR studies; ionophores anticancer activity; antibacterial activity; antitubercular activity; SAR studies; ionophores
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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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Antoszczak, M.; Maj, E.; Napiórkowska, A.; Stefańska, J.; Augustynowicz-Kopeć, E.; Wietrzyk, J.; Janczak, J.; Brzezinski, B.; Huczyński, A. Synthesis, Anticancer and Antibacterial Activity of Salinomycin N-Benzyl Amides. Molecules 2014, 19, 19435-19459.

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