Design, Synthesis, Characterization of New Carbamates of 4-Nitrophenylchloroformate and Their Antimicrobial and Antioxidant Activities: an In Vitro and In Silico Approach

A series of new carbamates of 4-nitrophenylchloroformate were synthesized in a simple nucleophilic substitution reaction with experimental simplicity and the products were characterized by IR, NMR, Mass spectra and CHN analysis. The title compounds were screened for the evaluation of in vitro and in silico antimicrobial and antioxidant activities by using appropriate methodologies. The obtained results naked that all the titled compounds exhibited the most promising antibacterial activity against B. subtilis, S. aureus, E. coli, K. pneumoniae and P. aeruginosa, antifungal activity against A. niger, A. flavus and R. arrhizus and strong antioxidant activity (DPPH and ABTS) when compared with the standard drugs streptomycin, norfloxacin and ascorbic acid. The higher content of activity was attributed to the compounds such as 11b, 11d, 11e, 11f and 11h akin to the rest of the compounds compared to the reference drugs. In addition, molecular docking studies provided support to the in vitro studies and revealed that the synthesized compounds have exhibited significant binding modes with high dock scores ranging from - 6.8 to - 9.8 against DNA Gyrase A when compared with the standard drugs, streptomycin and norfloxacin (- 6.9 and - 6.4), respectively. Hence, the compounds which exhibited promising activity in vitro and in silico will stand as the base for the discovery of new generation of antimicrobial and antioxidant agents.