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Medicinal Chemistry


ISSN (Print): 1573-4064
ISSN (Online): 1875-6638

Antimicrobial and Anti-biofilm Activity of Thiourea Derivatives Bearing 3-amino-1H-1,2,4-triazole Scaffold

Author(s): Joanna Stefanska, Karolina Stepien, Anna Bielenica, Daniel Szulczyk, Barbara Miroslaw, Anna E Koziol, Giuseppina Sanna, Filippo Iuliano, Silvia Madeddu, Michal Jozwiak and Marta Struga

Volume 12, Issue 5, 2016

Page: [478 - 488] Pages: 11

DOI: 10.2174/1573406412666151204003146

Price: $65


A set of 21 thiourea derivatives were prepared through reacting 3-amino-1H-1,2,4-triazole with the commercial aliphatic and aromatic isothiocyanates. The aliphatic isothiocyanate was used as reagent leading to substitution on NH atom of 3-aminotriazole ring, whereas the triazole amino group was substituted when isothiocyanate group was bonded to the Csp2 hybridized atom, e.g. an aryl or C=O fragment. All compounds were evaluated in vitro for the antimicrobial activity. The derivatives 1, 2, 4, 8, 9, 10 and 12 showed the highest inhibition against Gram-positive cocci (S. aureus and S. epidermidis). The observed MIC values were in the range of 4–32 μg/mL. Compounds were also tested for their in vitro antimicrobial activity against the hospital methicillin-resistant strains of S. aureus. The observed MIC values varied from 4 to 64 μg/mL. The products 4 and 10 effectively inhibited the formation of biofilms of the methicillin-resistant and standard strains of S. epidermidis. The compound 10 was found to be more promising with IC50 values of 2–6 μg/mL as compared to the control. Moreover, the cytotoxicity against the MT-4 cells of all studied thioureas was evaluated. The compound 18 was significantly cytotoxic (CC50 = 8 μM).

Keywords: Antimicrobial activity, 3-amino-1H-1, 2, 4-triazole, biofilm, cytotoxicity, thiourea derivatives.

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