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Synthesis, anticancer and antibacterial activity of salinomycin N-benzyl amides.


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.

SUBMITTER: Antoszczak M 

PROVIDER: S-EPMC6271077 | biostudies-literature | 2014 Nov

REPOSITORIES: biostudies-literature

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Synthesis, anticancer and antibacterial activity of salinomycin N-benzyl amides.

Antoszczak Michał M   Maj Ewa E   Napiórkowska Agnieszka A   Stefańska Joanna J   Augustynowicz-Kopeć Ewa E   Wietrzyk Joanna J   Janczak Jan J   Brzezinski Bogumil B   Huczyński Adam A  

Molecules (Basel, Switzerland) 20141125 12


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 Staphylo  ...[more]

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