N-Substituted N′-(2-alkylthio-4-chloro-5-methylbenzenesulfonyl) Guanidines – Antibacterial, Cytotoxic Activities and Theoretical Studies

Beata Żołnowska, Jarosław Sławiński, Aleksandra Grzonek, Anna Kędzia, Ewa Kwapisz, Anna Kawiak
Pol J Microbiol
2015; 64 (3):
ICID: 1170472
Article type: Short communication
IC™ Value: 6.00
Abstract provided by Publisher
A series of twenty nine N-substituted N′-(2-alkylthio-4-chloro-5-methylbenzenesulfonyl)guanidine derivatives bearing sulfonamide moiety have been screened in vitro for antibacterial activity against isolates from patients with infections of oral cavity, respiratory tract and intestinal tract. The majority of compounds exhibited antibacterial potency against anaerobic as well as aerobic bacteria strains at concentration in the range of 6.2 to 100 µg/ml. The most active series of guanidine derivatives belonged to 1-[4-chloro-5-methyl-2-(4-trifluoromethylbenzylthio)benzenesulfonyl]guanidines and  1-[4-chloro-5-methyl-2-(naphthalen-1-ylmethylthio)benzenesulfonyl]guanidines. 1-[4-Chloro-5-methyl-2-(4-trifluoromethylbenzylthio)benzenesulfonyl]-3-(3-sulfamoylphenyl)guanidine (13) showed very strong activity, with MIC ≤ 6.2 µg/ml against eleven bacteria strains belonged to Gram-positive anaerobes and aerobes. Furthermore, compound 13 exhibited promising activity toward highly resistant microorganisms such as methicillin-resistant Staphylococcus aureus and Enterococcus faecalis. It was found that, Parvimonas micra, Finegoldia magna, Peptostreptococcus anaerobius, Propionibacterium acnes showed the highest susceptibility toward investigated guanidines. Quantum chemical calculations of structural and electronic parameters was performed due to explain some differences in biological activity. Theoretical studies revealed that in the cases of P. micra, F. magna, P. acnes polar surface area (PSA) was the best descriptor to explain the different antibacterial activity of guanidines.

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