Exploring the Bioactivity of Primary Carbamates: Carbonic Anhydrase Inhibition Profiles, Antioxidant Potential, Antimicrobial Effect, and Molecular Docking Studies

Abstract

The biological potential of a series of primary carbamate derivatives was investigated, focusing on their inhibitory effects against two clinically significant human carbonic anhydrase isoenzymes, hCA I and hCA II. These enzymes are closely associated with various pathological conditions, including glaucoma, epilepsy, and certain types of cancer. The carbamate compounds, previously synthesized via a safer and more sustainable one-pot method from alcohols, were evaluated for their enzyme inhibition profiles as well as their antioxidant, antibacterial, and antifungal activities. The findings highlight key structure-activity relationships, particularly emphasizing the role of aromatic and electron-donating substituents in enhancing biological efficacy. This work contributes to the development of multifunctional small molecules with therapeutic relevance. Among the tested compounds, 3 g and 3f, featuring benzyl and methyl substituents, respectively, exhibited the highest inhibitory activities, with 3 g being the most potent. The antioxidant properties of the carbamates were assessed using DPPH radical scavenging, ABTS cation radical scavenging, and Fe3 + reducing assays. Compound 3 g demonstrated the strongest antioxidant activity, which can be attributed to the electron-donating effects of its benzyl and methyl substituents. Antimicrobial evaluations against a range of bacterial and fungal strains further revealed that compound 3 g possessed the most potent antibacterial and antifungal activities. Additionally, molecular docking studies were performed to provide complementary insights and support the experimental findings on the biological activities of the carbamate derivatives. Overall, this research underscores the potential of carbamate derivatives as multifunctional bioactive compounds with promising enzyme inhibition, antioxidant, and antimicrobial properties.