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Open AccessArticle

Synthesis and Antibacterial Activity of Difluoromethyl Cinnamoyl Amides

1
CONICET-Universidad de Buenos Aires, UMYMFOR, Buenos Aires C1428EGA, Argentina
2
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires C1428EGA, Argentina
3
CONICET-Universidad de Buenos Aires, IQUIBICEN, Buenos Aires C1428EGA, Argentina
4
Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires C1428EGA, Argentina
*
Authors to whom correspondence should be addressed.
Current address: SENASA, Dirección General de Laboratorios y Control Técnico, Dirección del Laboratorio Animal, Coordinación de Virología, Departamento de Cultivo Celular, Ministerio de Agroindustria, Buenos Aires C1063ACW, Argentina.
Academic Editors: Fernanda Borges, Jorge Garrido and Tiago Barros Silva
Molecules 2020, 25(4), 789; https://doi.org/10.3390/molecules25040789 (registering DOI)
Received: 29 December 2019 / Revised: 18 January 2020 / Accepted: 23 January 2020 / Published: 12 February 2020
(This article belongs to the Special Issue Cinnamic Acids and Analogs: Food and Health Applications)
Series of novel amides of isoferulic acid, where the phenolic hydroxyl was replaced by a difluoromethyl group, were synthesized and their in vitro antibacterial activities assayed against fourteen bacterial strains (six Gram-positive and eight Gram-negative). A one-pot methodology was developed to obtain the 3′-(difluoromethyl)-4′-methoxycinnamoyl amides using Deoxofluor® as a fluorinating agent. The N-isopropyl, N-isopentyl, and N-(2-phenylethyl) amides 11b, 11d and 11g were the most active and selective against Mycobacterium smegmatis (MIC = 8 µg/mL) with 11b and 11g displaying negligible or no cytotoxicity against HepG2 and A549 cells. Thirteen analogs of N-isopropylamide 11b were also synthesized and their antibacterial activity assayed. Results show that the difluoromethyl moiety enhanced antibacterial activity and selectivity towards M. smegmatis, changing the microorganism inhibition profile of the parent compound. The selectivity exhibited by some of the compounds towards M. smegmatis makes them potential leads in the search for new narrow spectrum antibiotics against M. tuberculosis. View Full-Text
Keywords: difluoromethyl group; cinnamic acid amides; antibacterial difluoromethyl group; cinnamic acid amides; antibacterial
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MDPI and ACS Style

Martínez, M.D.; Riva, D.A.; Garcia, C.; Durán, F.J.; Burton, G. Synthesis and Antibacterial Activity of Difluoromethyl Cinnamoyl Amides. Molecules 2020, 25, 789.

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