Synthesis, reactivity, in vitro boron neutron capture therapy assay, and molecular docking of fluorocyclocarboxyboranylamine. (19th May 2020)

• Record Type: Journal Article
• Authors: Zhu, Yinghuai; Cai, Jianghong; Zheng, Chong; Narayan S, Hosmane; Masao, Takagaki
• Is Part Of: Applied organometallic chemistry. Volume 34:Number 8(2020)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2020-05-19
• Subjects: antirheumatoid arthritis -- boron neutron capture synovectomy (BNCS) -- boron neutron capture therapy (BNCT) -- fluorocyclocarboxyboranylamine -- molecular docking; Organometallic chemistry -- Periodicals; Organometallic compounds -- Periodicals; 547.05
• DOI: 10.1002/aoc.5714
• Languages: English
• ISSNs: 0268-2605

Abstract

Abstract: The one‐pot reaction of Me3 NBH2 CN with Et3 O + BF4 − followed by addition of BF3 ·Et2 O and water produces a trimethylamine derivative of fluorocyclocarboxyboranylamine, Me3 NBH2 C(O2 BF2 NH2 ) (1 ) in 36.0% yield. Compound 1 undergoes exchange reaction between the exo‐Me3 N 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 1 H, 13 C, 11 B, and 19 F 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. Abstract : Fluorocyclocarboxyboranylamines can conduct amine exchange reactions. Fluorocyclocarboxyboranylamines show high anti‐rheumatoid arthritis efficacy in vitro. Fluorocyclocarboxyboranylamines show high antitumor efficacy in vitro.