AUTHOR=Rosa Wilian C. , Rocha Inaiá O. , Rodrigues Melissa B. , Coelho Helena S. , Denardi Laura B. , Ledur Pauline C. , Zanatta Nilo , Acunha Thiago V. , Iglesias Bernardo A. , Bonacorso Helio G. 

TITLE=Novel Alkyl(aryl)-Substituted 2,2-Difluoro-6-(trichloromethyl)-2H-1,3,2-oxazaborinin-3-ium-2-uides: Synthesis, Antimicrobial Activity, and CT-DNA Binding Evaluations

JOURNAL=Frontiers in Pharmacology

VOLUME=11

YEAR=2020

URL=https://www.frontiersin.org/journals/pharmacology/articles/10.3389/fphar.2020.01328

DOI=10.3389/fphar.2020.01328

ISSN=1663-9812

ABSTRACT=<p>The synthesis, antimicrobial activity evaluations, biomolecule-binding properties (DNA), and absorption and emission properties of a new series of (<italic>Z</italic>)-1,1,1-trichloro-4-alkyl(aryl)amino-4-arylbut-3-en-2-ones <bold>(4, 5)</bold> and 2,2-difluoro-3-alkyl(aryl)amino-4-aryl-6-(trichloromethyl)-2<italic>H</italic>-1,3,2-oxazaborinin-3-ium-2-uides <bold>(6, 7)</bold> in which 3(4)-alkyl(aryl) = H, Me, <italic>iso</italic>-propyl, <italic>n</italic>-butyl, C<sub>6</sub>H<sub>5</sub>, 4-CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>, 4-CH<sub>3</sub>OC<sub>6</sub>H<sub>4</sub>, 4-NO<sub>2</sub>C<sub>6</sub>H<sub>4</sub>, 4-FC<sub>6</sub>H<sub>4</sub>, 4-BrC<sub>6</sub>H<sub>4</sub>, 2-naphthyl, is reported. A series of β-enaminoketones <bold>(4, 5)</bold> is synthesized from the O,N-exchange reaction of some amines <bold>(3)</bold> with (<italic>Z</italic>)-1,1,1-trichloro-4-methoxy-4-aryl-but-3-en-2-ones <bold>(1, 2)</bold> at 61–90% yields. Subsequently, reactions of the resulting β-enaminoketones with an appropriate source of boron (BF<sub>3</sub>.OEt<sub>2</sub>) gave the corresponding oxazaborinine derivatives <bold>(6, 7)</bold> at 50–91% yields. UV-Vis and emission properties of biomolecule-binding properties for the DNA of these new BF<sub>2</sub>-β-enamino containing CCl<sub>3</sub> units were also evaluated. Some compounds from the present series also exhibited potent antimicrobial effects on various pathogenic microorganisms at concentrations below those that showed cytotoxic effects. Compounds <bold>4d, 4e, 6e</bold>, and <bold>6f</bold> showed the best results and are very significant against <italic>P. zopfii</italic>, which causes diseases in humans and animals.</p>