Synthesis, reactivity, in vitro boron neutron capture therapy assay, and molecular docking of fluorocyclocarboxyboranylamine
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Applied Organometallic Chemistry
The 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. Compound 1 undergoes 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 by 1H, 13C, 11B, and 19F nuclear magnetic resonance spectroscopy; Fourier-transform infrared spectroscopy; and elemental analyses and the crystal structure of 1 was determined to confirm its molecular geometry. The in vitro killing effects of 1, 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.
antirheumatoid arthritis, boron neutron capture synovectomy (BNCS), boron neutron capture therapy (BNCT), fluorocyclocarboxyboranylamine, molecular docking
Zhu, Yinghuai; Cai, Jianghong; Zheng, Chong; Narayan S, Hosmane; and Masao, Takagaki, "Synthesis, reactivity, in vitro boron neutron capture therapy assay, and molecular docking of fluorocyclocarboxyboranylamine" (2020). NIU Bibliography. 620.
Department of Chemistry and Biochemistry