Synthesis and anthelmintic assessment of 2-((Dimethylamino)methyl) cyclohexanone mannich base derivatives

Abstract

The emergence of drug resistance is driven by the evolutionary pressure of survival which presents a significant challenge to modern medicine. The continuous use of anthelmintic drugs could lead to long-term resistance to target proteins (receptors) and result in various side effects. There is a need to synthesize novel anthelmintic drugs with increased potency, enhanced specificity to a particular target site, and reduced or devoid of side effects. The present work aimed at using Mannich base (a class of structurally heterogeneous chemical compounds made from various substrates using the Mannich reaction) to synthesie and characterize (2-((dimethylamino)methyl) cyclohexanone, and its derivatives using column chromatography, spectroscopic (FTIR, NMR) methods, and assessing their anthelmintic activities. Anthelmintic (Milsonia ghanensis (earthworm)), assay was performed on the synthesized compounds (Mannich Base 1, Derivatives 3 and 5, and Model Compounds 2 and 4) and cyclohexanone. The action of the synthesized compounds on Milsonia ghanensis worms was concentration-dependent, with the least concentration (0.5 mg/mL) paralyzing and killing M. ghanensis after the maximal exposure time. The synthesized compounds 1, 2, 3, 4, and 5 not only exhibit high anthelmintic activity but also cause both paralysis and death of the M. ghanensis earthworms at a rate much higher than albendazole. The results indicate that 2-((dimethylamino)methyl) cyclohexanone and its derivatives have anthelmintic activities.