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

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Atmaca U., Alp C., Akincioglu H., Karaman H. S., Gülçin İ., Çelik M.

Journal of Molecular Structure, cilt.1239, 2021 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1239
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1016/j.molstruc.2021.130492
  • Dergi Adı: Journal of Molecular Structure
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Anahtar Kelimeler: Hypervalent iodine, Carbonic anhydrase, A-sulfonoxyketones, A-hydroxyketones, Acetylcholinesterase, Butyrylcholinesterase, ANHYDRASE INHIBITORY PROPERTIES, CARBONIC-ANHYDRASE, CRYSTAL-STRUCTURE, 1ST SYNTHESIS, ANTICHOLINERGIC ACTIVITIES, SULFONAMIDE DERIVATIVES, ASYMMETRIC-SYNTHESIS, HYDROXY KETONE, ACETYLCHOLINESTERASE, BUTYRYLCHOLINESTERASE
  • Atatürk Üniversitesi Adresli: Evet

Özet

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.