A series of symmetrical imidazolinium chloride salts bearing secondary N-alkyl substituents were synthesized in good yield by the reaction of N,N'-dialkylethane-1,2-diamines and HC(OEt)(3) in the presence of NH4Cl. These salts were characterized by spectroscopic methods. All compounds were tested as enzyme inhibitory agents. These novel symmetrical imidazolinium chloride salts derivatives (3a-h) effectively inhibited the cytosolic hCA I and hCA II, BChE, alpha-glycosidase and AChE with K-i values in the range of 18.41-121.73 nM for hCA I, 12.50-63.12 nM for hCA II, 3.72-34.58 nM for AChE, 5.50-32.36 nM for BChE, and 94.72-364.51 nM for alpha-glycosidase, respectively. CA isoenzymes play a crucial roles including acid-base balance homeostasis by excreting and secreting protons (H+) due to the CO2 hydration, HCO3- reabsorption mechanisms, and renal NH4+ output. Also, the molecular modeling is an implementation for estimation of the binding proximity of symmetrical imidazolinium chloride salts bearing secondary wingtip groups and their inhibition mechanisms and kinetics in atomic levels at the catalytic domains. (C) 2018 Elsevier B.V. All rights reserved.