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Molecules 2018, 23(11), 2853;

Pentafluorosulfanyl-containing Triclocarban Analogs with Potent Antimicrobial Activity

Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia i Ciències de l′Alimentació, and Institute of Biomedicine (IBUB), Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain
Bacterial Infections and Antimicrobial Therapies, Institute for Bioengineering of Catalonia (IBEC), The Barcelona Institute of Science and Technology, Baldiri Reixac 15-21, 08028 Barcelona, Spain
Departament de Genètica i de Microbiologia, Facultat de Biociències, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain
These authors contributed equally to this paper.
Authors to whom correspondence should be addressed.
Academic Editor: Marta Barniol-Xicota
Received: 16 October 2018 / Revised: 25 October 2018 / Accepted: 26 October 2018 / Published: 2 November 2018
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Concerns have been raised about the long-term accumulating effects of triclocarban, a polychlorinated diarylurea widely used as an antibacterial soap additive, in the environment and in human beings. Indeed, the Food and Drug Administration has recently banned it from personal care products. Herein, we report the synthesis, antibacterial activity and cytotoxicity of novel N,N′-diarylureas as triclocarban analogs, designed by reducing one or more chlorine atoms of the former and/or replacing them by the novel pentafluorosulfanyl group, a new bioisostere of the trifluoromethyl group, with growing importance in drug discovery. Interestingly, some of these pentafluorosulfanyl-bearing ureas exhibited high potency, broad spectrum of antimicrobial activity against Gram-positive bacterial pathogens, and high selectivity index, while displaying a lower spontaneous mutation frequency than triclocarban. Some lines of evidence suggest a bactericidal mode of action for this family of compounds. View Full-Text
Keywords: antibacterial; Gram-positive; N,N′-diarylureas; pentafluorosulfanyl; Staphylococcus aureus; triclocarban antibacterial; Gram-positive; N,N′-diarylureas; pentafluorosulfanyl; Staphylococcus aureus; triclocarban

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Pujol, E.; Blanco-Cabra, N.; Julián, E.; Leiva, R.; Torrents, E.; Vázquez, S. Pentafluorosulfanyl-containing Triclocarban Analogs with Potent Antimicrobial Activity. Molecules 2018, 23, 2853.

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