Publikationsdatum:
2018-03-06
Beschreibung:
Conscious of the potential bioactivity of fluorine, an investigation was conducted using various fluorine-containing diaryliodonium salts in order to study and compare their biological activity against human lymphoma U937 cells. Most of the compounds tested are well-known reagents for fluoro-functionalized arylation reactions in synthetic organic chemistry, but their biological properties are not fully understood. Herein, after initially investigating 18 fluoro-functionalized reagents, we discovered that the ortho -fluoro-functionalized diaryliodonium salt reagents showed remarkable cytotoxicity in vitro. These results led us to synthesize more compounds, previously unknown sterically demanding diaryliodonium salts having a pentafluorosulfanyl (SF 5 ) functional group at the ortho -position, that is, unsymmetrical ortho -SF 5 phenylaryl-λ 3 -iodonium salts. Newly synthesized mesityl(2-(pentafluoro-λ 6 -sulfanyl)phenyl)iodonium exhibited the greatest potency in vitro against U937 cells. Evaluation of the cytotoxicity of selected phenylaryl-λ 3 -iodonium salts against AGLCL (a normal human B cell line) was also examined. Beilstein J. Org. Chem. 2018, 14, 364–372. doi:10.3762/bjoc.14.24
Schlagwort(e):
biological activitydiaryliodonium saltfluorinehypervalent iodinelymphomapentafluorosulfanyl
Digitale ISSN:
1860-5397
Thema:
Chemie und Pharmazie
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