1, 1-Difluoro-3-aryl(heteroaryl)-1H-pyrido[1, 2-c][1, 3, 5, 2]oxadiazaborinin-9-ium-1-uides: synthesis; structure; and photophysical, electrochemical, and BSA-binding studies. (11th January 2018)

• Record Type: Journal Article
• Authors: Bonacorso, Helio G.; Calheiro, Tainara P.; Iglesias, Bernardo A.; Acunha, Thiago V.; Franceschini, Steffany Z.; Ketzer, Alex; Meyer, Alexandre R.; Rodrigues, Letícia V.; Nogara, Pablo A.; Rocha, João B. T.; Zanatta, Nilo; Martins, Marcos A. P.
• Is Part Of: New journal of chemistry. Volume 42:Number 3(2018)
• Page Start: 1913
• Page End: 1920
• Publication Date: 2018-01-11
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c7nj04032f
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : New fluorinated pyridine-based boron heterocycles were easily prepared and fully characterized. Abstract : This paper presents a series of six examples of 1, 1-difluoro-3-aryl(heteroaryl)-1 H -pyrido[1, 2- c ][1, 3, 5, 2]oxadiazaborinin-9-ium-1-uides (2 )—in which aryl(heteroaryl) = phenyl, 4-MeC6 H4, 4-N(CH3 )2 C6 H4, 4-NO2 C6 H4, 2-naphthyl, and 2-thienyl—as pyridine-based boron heterocycles with variable ligand structures. The heterocycles2 were easily synthesized at yields of 51–70% from reactions—at room temperature for 24 h—of simple N -(pyridin-2-yl)benzamides (1 ) with BF3 ·Et2 O, and they were fully characterized by 1 H-, 13 C-, 19 F-, and 11 B-NMR spectroscopy, GC-MS, and X-ray diffractometry. The optical and electrochemical properties of2 (UV-vis spectra, fluorescence spectra, quantum yield calculations, Stokes' shifts, redox potentials, and DFT calculations) were determined and discussed. BSA-binding experiments and molecular docking studies of new complexes2 were performed and correlated between each other.