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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amides / chemical synthesis*
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Amides / chemistry
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Amides / pharmacology*
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Anti-Bacterial Agents / chemical synthesis*
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / pharmacology*
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology*
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Antitubercular Agents / pharmacology
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Carbon-13 Magnetic Resonance Spectroscopy
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Cell Line, Tumor
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Crystallography, X-Ray
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Humans
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Hydrogen Bonding
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Methicillin-Resistant Staphylococcus aureus / drug effects
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Microbial Sensitivity Tests
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Mycobacterium tuberculosis / drug effects
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Proton Magnetic Resonance Spectroscopy
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Pyrans / chemical synthesis*
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Pyrans / chemistry
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Pyrans / pharmacology*
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Spectrometry, Mass, Electrospray Ionization
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Spectroscopy, Fourier Transform Infrared
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Staphylococcus epidermidis / drug effects
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Structure-Activity Relationship
Substances
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Amides
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Anti-Bacterial Agents
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Antineoplastic Agents
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Antitubercular Agents
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Pyrans
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salinomycin