Abstract
The aim of this study was preparation of new derivatives based on 2-((4-chlorophenoxy)methyl)-N-(arylcarbamothioyl)benzamide structure; the new compounds were characterized by IR, NMR (1H, 13C) spectroscopy, and elemental analysis. The obtained compounds were evaluated for their in vitro antimicrobial activity against planktonic and biofilm-embedded microbial cells (Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, Pseudomonas aeruginosa, Candida albicans), by qualitative and quantitative assays. Some of the compounds revealed promising antibacterial and antifungal activities, with low minimum inhibitory concentration values between 0.15 and 2.5 mg/mL and minimal biofilm eradication concentrations of 0.019–2.5 mg/mL. To investigate the potential target of their antibacterial activity, in silico drug-likeness and molecular docking screenings on Staphylococcus aureus DNA gyrase were performed. The compound with the best antibacterial activity (1g) was docked into topoisomerase II DNA gyrase enzymes (PDB ID: 2XCS) and showed valuable interactions with the target protein along with good docking scores, suggesting that it can act by the inhibition of DNA replication. The tested compounds exhibited only a poor antioxidant activity, as revealed by the in vitro assay using 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay.
Highlights
The new compounds (1a–g) with the thiourea skeleton were prepared according to the Figure 2, from 2-(4-chlorophenoxymethyl)benzoyl isothiocyanate (2) and primary amines
The isothiocyanate was obtained by reaction of 2-(4-chlorophenoxymethyl)benzoyl chloride (3) with ammonium thiocyanate
The acid chloride was obtained from 2-(4-chlorophenoxymethyl)benzoic acid
Summary
The thiourea thiourea skeleton skeleton isisfound foundininthe thestructure structureof of some drugs, such noxytiolin. The some drugs, such are are noxytiolin [1], [1], an an anti-infective drug, sulfathiourea [2], a bacteriostatic sulfonamide derivative, loflucarban [3]. With anti-infective drug, sulfathiourea [2], a bacteriostatic sulfonamide derivative, loflucarban [3] with a thiocarbanilide structure, structure, having having antifungal antifungal properties, properties, thiophanate thiophanate [4]. [6] is is a thiourea thiourea drug known known as an effective anti-tuberculosis drug, active against against a Thiocarlide range of multidrug-resistant strains of Mycobacterium tuberculosis which has been used used clinically. [6] is is a thiourea thiourea drug known known as an effective anti-tuberculosis drug, active against against a Thiocarlide range of multidrug-resistant strains of Mycobacterium tuberculosis which has been used used clinically. clinically.
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