Abstract
In the present paper, we report the synthesis and evaluation of in vitro antimicrobial activities of aziridine-thiourea derivatives. A series of aziridines in reaction with isocyanates and isothiocyanates to obtain urea and thiourea derivatives were used. The structures of all new products were confirmed based on spectroscopic data (1H-NMR, 13C-NMR, HR-MS). These compounds were screened for their in vitro antimicrobial activity against a panel of Gram-positive and Gram-negative strains of bacteria. Six of the tested compounds appeared to be promising agents against reference strains of Escherichia coli, Staphylococcus aureus and Staphylococcus epidermidis. Subsequently, compounds exhibiting promising antibacterial activity were tested against twelve clinical isolates of S. aureus from three different sources of infection. The most bactericidal compounds (MIC = 16–32 µg/mL) showed better antibacterial activity against MRSA than ampicillin and streptomycin. The in vitro cytotoxicity analysis on L929 murine fibroblast and HeLa human tumor cell line using the MTT assay allowed us to select the least toxic compounds for future investigation.
Highlights
Aziridines are nitrogen-containing, three-membered ring heterocycles, which are widely known as useful reactive intermediates in the synthesis of amino acid derivatives, azomethine ylides or chiral amino alcohols [1,2,3]
We focused on the design and synthesis of structurally novel urea and thiourea aziridine derivatives and evaluation of their biological activity based on the fact that many thiourea aziridine derivatives and evaluation of their biological activity based on the fact that many aziridine ring containing compounds have demonstrated antibacterial and cytotoxic activities
The presence of sulphur atom is a principal factor for antibacterial properties of aziridine derivatives
Summary
Aziridines are nitrogen-containing, three-membered ring heterocycles, which are widely known as useful reactive intermediates in the synthesis of amino acid derivatives, azomethine ylides or chiral amino alcohols [1,2,3]. They are used as chiral auxiliaries and chiral ligands in asymmetric synthesis [4,5,6,7,8] or in fused heterocycles [9]. Physiological effect of mitomycin C relies on aziridine ring opening and interaction with guanine nucleobase of DNA in the alkylation reaction This leads to covalent interstrand DNA–DNA crosslink formation, inhibition of replication and to cell death. Mitochondria swell, Molecules 2018, 23, 45; doi:10.3390/molecules23010045 www.mdpi.com/journal/molecules
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