Synthesis, characterization, crystal structure and bioactivity properties of the benzimidazole-functionalized PEPPSI type of Pd(II)NHC complexes

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Dasgin S., Gök Y., Barut Celepci D., Taslimi P., Izmirli M., Aktaş A., ...Daha Fazla

JOURNAL OF MOLECULAR STRUCTURE, cilt.1228, 2021 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1228
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1016/j.molstruc.2020.129442
  • 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: Acetylcholinesterase, Butyrylcholinesterase, N-heterocyclic carbene, PEPPSI complex, X-ray diffraction, alpha-Glycosidase, HETEROCYCLIC CARBENE COMPLEXES, CATALYTIC-ACTIVITY, CARBONIC-ANHYDRASE, ARYL CHLORIDES, ACETYLCHOLINESTERASE, SONOGASHIRA, INHIBITORS, BUTYRYLCHOLINESTERASE, STABILIZATION, PRECATALYST
  • Dokuz Eylül Üniversitesi Adresli: Evet

Özet

Herein, six new benzimidazole-functionalized Pd-based complexes bearing N-propylphthalimide group were synthesized. These new PEPPSI type of Pd(II)NHC complexes (PEPPSI: Pyridine Enhanced Precatalyst Preparation, Stabilization and Initiation) were prepared from the N-propylphthalimide substituted benzimidazolium salts, palladium chloride (PdCl2) and 3-chloropyridine. The structures of all (NHC)PdX2(3-chloropyridine) complexes have been clearly characterized by using NMR (H-1 and C-13), FTIR spectroscopic method, and elemental analysis techniques. Also, the structures of three of the (NHC)PdX2(3-chloropyridine) complexes were confirmed by single-crystal X-ray diffraction. Also, novel N-propylphthalimide-substituted (NHC)PdX 2 (3-chloropyridine) complexes effectively inhibited acetylcholinesterase (AChE), with Ki values in the range of 0.54 +/- 0.10 to 3.01 +/- 0.63 mu M. For butyryl-cholinesterase (BChE) was obtained with Ki values in the range of 0.82 +/- 0.11 to 5.03 +/- 0.86 mu M. For alpha-glycosidase (alpha-Gly) the most effective Ki values of 1c, 1d, and 1b were with Ki values of 23.83 +/- 5.98, 26.04 +/- 7.11, and 30.61 +/- 3.85 mu M, respectively. All novel N-propylphthalimide-substituted PEPPSI complexes and control compounds had almost similar inhibition profiles. (C) 2020 Elsevier B.V. All rights reserved.