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

• Published in: Journal of molecular structure 2021-09, Vol.1239, p.130492, Article 130492
• Main Authors: Atmaca, Ufuk, Alp, Cemalettin, Akincioglu, Hulya, Karaman, Halide Sedef, Gülçin, İlhami, Çelik, Murat
• Format: Article
• Language: English
• Subjects: Acetylcholinesterase; Butyrylcholinesterase; Carbonic anhydrase; Hypervalent iodine; Α-hydroxyketones; Α-sulfonoxyketones
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2021.130492

•Novel hypervalent iodine was synthesized. in mild conditions.•α-Sulfonoxylation of ketones using novel hypervalent iodine was accomplished with non-metal catalyts.•α-Hydroxy ketones were synthesized reaction of α-sulfonoxy ketones with Li/NH3.•Inhibitory potentials of synthesized novel α-sulfonoxy ketones were investigated for AChE, BChE, hCA I, and hCA II enzymes.•Novel α-sulfonoxy ketones were found to have strong inhibitory effects on these enzymes. The novel di((camphorsulfonyl)oxy)iodo]benzene (DCIB) was synthesized from [Bis(trifluoroacetoxy)iodo]benzene in the mild conditions. The α-sulfonoxylation of various ketones with novel hypervalent iodine was reported in excellent yield. α-Hydroxyketones were synthesized from α-sulfonoxy compounds (caphorsulfonoxy ketones) with Li/NH3(g) at -20 °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 α-sulfonoxy ketones were found to have strong inhibition effects on these metabolic enzymes. IC50 values and Ki values were determined for each compounds and compared with putative and positive controls. The synthesized α-sulfonoxy ketone compounds showed Ki values of in range of 73.2–406.0 µM against hCA I, and 57.12–526.05 µM against hCA II closely associated with various physiological and pathological processes in living organisms. On the other hand, Ki values were found in range of 28.80–140.3 µM against AChE, and 7.186–40.0 µM against BChE enzymes. Within the scope of the study, the inhibition types of the α-sulfonoxy ketones with novel hypervalent iodine were evaluated. Camphorsulfonoxy moiety caused to inhibition of the enzymes through hydrophobic interaction and hydrogen bond. [Display omitted]