Abstract
AbstractThe one‐pot reaction of Me3NBH2CN with Et3O+BF4−followed by addition of BF3·Et2O and water produces a trimethylamine derivative of fluorocyclocarboxyboranylamine, Me3NBH2C(O2BF2NH2) (1) in 36.0% yield. Compound1undergoes exchange reaction between the exo‐Me3N moiety and piperidine or pyridine to produce the corresponding piperidine‐substituted fluorocyclocarboxyboranylamine (2) or pyridine‐substituted fluorocyclocarboxyboranylamine (3) in 51.2% or 42.4% yields, respectively. The new compounds were characterized by1H,13C,11B, and19F nuclear magnetic resonance spectroscopy; Fourier‐transform infrared spectroscopy; and elemental analyses and the crystal structure of1was determined to confirm its molecular geometry. Thein vitrokilling effects of1, along with its toxicity measurements and molecular docking interactions with matrix metalloproteinases showed a potential promise of such species as both boron neutron capture therapy and boron neutron capture synovectomy agents in the treatment of tumors and rheumatoid arthritis, respectively, in the presence of slow neutrons.
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