Title:Synthesis of Mannich Bases by Two Different Methods and Evaluation of their Acetylcholine Esterase and Carbonic Anhydrase Inhibitory Activities
Volume: 14
Issue: 5
Author(s): Halise I. Gul*, Alkan Demirtas, Gokbay Ucar, Parham Taslimi and İlhami Gulcin
Affiliation:
- Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk University, Erzurum 25240,Turkey
Keywords:
Acetylcholine esterase, carbonic anhydrase, conventional heating, Mannich bases, microwave irradiation.
Abstract: Background: Mannich bases are an important compounds in medicinal chemistry. They have wide
range of biological activities including carbonic anhydrase (CA) inhibitory and acetylcholine esterase
inhibitory (AChE) activities.
Objective: It was aimed to synthesize Mannich bases, 1-aryl-3-(morpholin-4-yl/piperidin-1-yl)-1-
propanone hydrochloride, by microwave irradiation and conventional heating methods to compare the
methods in terms of reaction times and yields and to investigate their inhibitory effects on AChE
enzyme and CA isoenzymes.
Method: Mannich bases were synthesized using conventional heating and microwave irradiation
methods under different reaction conditions. Inhibitory effects of the compounds on CA isoenzymes and
AChE were evaluated according to literature procedure.
Results: IC50 and Ki values of the compounds were evaluated against hCA I, II and AChE. The
compounds had more potent or equal Ki values with the references used.
Conclusion: This study makes an important contribution to the Mannich base library in terms of
synthetic strategy. According to IC50 or Ki values the compounds 6 in Series A with morpholine and and
15 in Series B with piperidine towards both hCA I and/or II isoenzymes and the compounds 4 in Series
A and 11, 13, 14, 15, 16, and 18 in Series B towards AChE seemed the leader compounds of the study.
