TY - JOUR A1 - Das, Prajwalita A1 - Tokunaga, Etsuko A1 - Akiyama, Hidehiko A1 - Doi, Hiroki A1 - Saito, Norimichi A1 - Shibata, Norio T1 - Synthesis of fluoro-functionalized diaryl-λ3-iodonium salts and their cytotoxicity against human lymphoma U937 cells JF - Beilstein Journal of Organic Chemistry PY - 2018/// VL - 14 SP - 364 EP - 372 SN - 1860-5397 DO - 10.3762/bjoc.14.24 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.14.24 KW - biological activity KW - diaryliodonium salt KW - fluorine KW - hypervalent iodine KW - lymphoma KW - pentafluorosulfanyl N2 - 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 (SF5) functional group at the ortho-position, that is, unsymmetrical ortho-SF5 phenylaryl-λ3-iodonium salts. Newly synthesized mesityl(2-(pentafluoro-λ6-sulfanyl)phenyl)iodonium exhibited the greatest potency in vitro against U937 cells. Evaluation of the cytotoxicity of selected phenylaryl-λ3-iodonium salts against AGLCL (a normal human B cell line) was also examined. ER -