Two new series of pyrazolobenzothiazine-based carbothioamides (<b>3a-o</b> and <b>4a-o</b>) were synthesized using saccharin as the starting material. The synthesized derivatives were investigated for their ability to inhibit monoamine oxidases (MAO). Compound <b>3b</b> was found to be a very potent MAO-A inhibitor with an IC<sub>50</sub> value of 0.003 ± 0.0007 μM, while compound <b>4d</b> was the most effective inhibitor of MAO-B having an IC<sub>50</sub> value of 0.02 ± 0.001 μM. Molecular docking studies were performed to identify the probable binding modes in the active site of the monoamine oxidase enzymes. The synthetic and computational investigations in the current work suggested that these newly identified inhibitors may serve as a powerful starting point for the exploration and optimization of potential therapeutic agents targeting Parkinson's disease.