Novel hypervalent iodine catalyzed synthesis of α-sulfonoxy ketones: Biological activity and molecular docking studies

The novel di((camphorsulfonyl)oxy)iodo]benzene (DCIB) was synthesized from [Bis(trifluoroacetoxy)iodo]benzene in the mild conditions. The alpha-sulfonoxylation of various ketones with novel hypervalent iodine was reported in excellent yield. alpha-Hydroxyketones were synthesized from alpha-sulfonoxy compounds (caphorsulfonoxy ketones) with Li/NH3(g) at -20 degrees C in THF. Then, some biochemical studies including several enzyme inhibition linked some global diseases were carried out. For this purpose, the inhibitory potentials of synthesized novel camphorsulfonoxy ketones were investigated against hCA I, and hCA II isoenzymes, AChE, and BChE enzymes. When the results were evaluated, novel alpha-sulfonoxy ketones were found to have strong inhibition effects on these metabolic enzymes. IC50 values and K-i values were determined for each compounds and compared with putative and positive controls. The synthesized alpha-sulfonoxy ketone compounds showed K-i values of in range of 73.2-406.0 mu M against hCA I, and 57.12-526.05 mu M against hCA II closely associated with various physiological and pathological processes in living organisms. On the other hand, K-i values were found in range of 28.80-140.3 mu M against AChE, and 7.186-40.0 mu M against BChE enzymes. Within the scope of the study, the inhibition types of the alpha-sulfonoxy ketones with novel hypervalent iodine were evaluated. Camphorsulfonoxy moiety caused to inhibition of the enzymes through hydrophobic interaction and hydrogen bond. (C) 2021 Elsevier B.V. All rights reserved.

Automated summary

The novel compound DCIB was synthesized under mild conditions and used for alpha-sulfonoxylation of various ketones to produce alpha-hydroxyketones. Biochemical studies showed that the synthesized alpha-sulfonoxy ketones had strong inhibitory effects on metabolic enzymes. The inhibition of enzymes by the camphorsulfonoxy moiety was attributed to hydrophobic interactions and hydrogen bonding.