Abstract
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.
Highlights
In the last 20 years, antimicrobial resistance has been recognized as a serious public health problem.The increased resistance of pathogenic microorganisms is related to the misuse/abuse of antibiotics and to their natural adaptation and evolution to marketed antimicrobial compounds [1,2,3]
This dangerous rise of pathogenic bacteria that are resistant to existing antibiotics constitutes a global human health threat and requires a continuous search for new chemical entities [4,5]
Amide to evaluate the effect the resulting of isoferulic on antibacterial activity activity
Summary
The increased resistance of pathogenic microorganisms is related to the misuse/abuse of antibiotics and to their natural adaptation and evolution to marketed antimicrobial compounds (e.g., via biofilm formation, gene transfer from resistant counterparts, efflux pumps, cellular permeability, enzymes that confer resistance, and natural evolutionary mutations) [1,2,3] This dangerous rise of pathogenic bacteria that are resistant to existing antibiotics constitutes a global human health threat and requires a continuous search for new chemical entities [4,5]. Effective with a wide range of pathogens, are important for first line treatment of bacterial infections as well as for prevention in risk situations (e.g., surgical procedures, organ transplant, etc.) Their use damages the gut microbiota and favors the development of resistance mechanisms that may be readily transferred across. Once the pathogen has been identified, narrow spectrum species
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