Novel aryl(heteroaryl)-substituted (pyrimidyl)benzamide-based BF2 complexes: Synthesis, photophysical properties, BSA-binding, and molecular docking analysis.

Abstract This paper presents a new family of pyrimidine-based BF 2 complexes. The series contains six examples of 1,1-difluoro-3-aryl(heteroaryl)-1 H -pyrimido[1,2- c ][1,3,5,2]oxadiazaborinin-9-ium-1-uides (2) — in which aryl(heteroaryl) = phenyl, 4-MeC 6 H 4 , 4-N(CH 3) 2 C 6 H 4 , 4-NO 2 C 6 H 4 , 2-naphthyl, and 2-thienyl. The heterocycles 2 were easily synthesized at yields of 50–68% from reactions — at room temperature for 24 h — of simple N -(pyrimidin-2-yl)benzamides (1) with BF 3 ·Et 2 O, and they were fully characterized by 1H-, 13C-, 19F, 11B-NMR, GC–MS, and X-ray diffractometry. Moreover, the photophysical properties, TD-DFT analysis, BSA-binding experiments, and molecular docking studies for the new organoboron complexes 2 were determined, presented, discussed, and compared with similar compounds that have already been described. Graphical abstract Image 1 Highlights • A series of novel pyrimidine-based BF 2 complexes is synthesized and studied. • Multinuclear NMR and X-ray diffraction data are used for structural elucidation. • UV–vis, fluorescence, quantum yield and Stokes shift are presented and discussed. • Bio-interaction results as BSA-binding studies and molecular docking are reported. [ABSTRACT FROM AUTHOR]