ABSTRACT
The novel N-propylphthalimide-substituted and 4-vinylbenzyl-substituted N-heterocyclic carbene (NHC) precursors were synthesized by N-substituted benzimidazolium with aryl halides. The novel N-propylphthalimide-substituted and 4-vinylbenzyl-substituted NHC precursors have been characterized by using 1 H NMR, 13 C NMR, FTIR spectroscopy, and elemental analysis techniques. They were tested for the inhibition of AChE and hCA enzymes and demonstrated efficient inhibition profiles with Ki values in the range of 351.0-1269.9 nM against hCA I, 346.6-1193.1 nM against hCA II, and 19.0-76.3 nM against AChE. On the other hand, acetazolamide, a clinically used molecule, utilized as CA inhibitor, obtained a Ki value of 1246.7 nM against hCA I and 1407.6 nM against hCA II. Additionally, tacrine inhibited AChE and obtained a Ki value of 174.6 nM.
Subject(s)
Benzimidazoles/pharmacology , Carbonic Anhydrase Inhibitors/pharmacology , Cholinesterase Inhibitors/pharmacology , Drug Design , Iron Chelating Agents/pharmacology , Nootropic Agents/pharmacology , Phthalimides/pharmacology , Benzimidazoles/chemical synthesis , Benzimidazoles/chemistry , Carbonic Anhydrase Inhibitors/chemical synthesis , Carbonic Anhydrase Inhibitors/chemistry , Carbonic Anhydrases/chemistry , Carbonic Anhydrases/metabolism , Cholinesterase Inhibitors/chemical synthesis , Cholinesterase Inhibitors/chemistry , Humans , Iron Chelating Agents/chemical synthesis , Iron Chelating Agents/chemistry , Isoenzymes/antagonists & inhibitors , Isoenzymes/metabolism , Kinetics , Molecular Structure , Nootropic Agents/chemical synthesis , Nootropic Agents/chemistry , Phthalimides/chemical synthesis , Phthalimides/chemistry , Structure-Activity RelationshipABSTRACT
This study reports the synthesis, characterisation and antimicrobial activity of five novel silver N-heterocyclic carbene (Ag-NHC) complexes obtained by N-propylphthalimide and N-methyldioxane substituted benzimidazolium salts with silver oxide. The reactions were performed at room temperature for 24 h in the absence of light. The obtained complexes were identified and characterised by (1)H and (13)C NMR, FT-IR and elemental analysis techniques. The minimum inhibitory concentration (MIC) of the complexes was determined for E. coli, P. aeruginosa, E. faecalis, S. aureus, C. tropicalis and C. albicans in vitro through agar and broth dilution. The results indicated that these complexes exhibit antimicrobial activity. In particular, complex 3 presented the significant broad spectrum antimicrobial activity.
