Carbamates of sulfathiazole and methyl tryptophanate: Synthesis, antimicrobial activity and docking studies against DNA gyrase A.

It is well demonstrated that bacteria have become resistant to common medications recently and it is considered to be one of the major threats to human health. The research on innovative antimicrobial agents explores a vast and interesting subject area. Therefore, a series of new carbamate derivatives of sulfathiazole 6a-e, a common oral antimicrobial drug and methyl tryptophanate 8a-e, N-methyl -amino acid ester containing indole moiety have been synthesized. Structures of the title products have been elucidated by spectral analyses like IR, NMR (¹H and ¹³C), mass and elemental composition. The compounds have been evaluated for their in vitro antimicrobial activity including minimum inhibitory concentrations (MICs). Whereas, three carbamate derivatives of sulfathiazole 6a, 6b and 6e and one derivative of methyl tryptophanate 8a show promising antibacterial activity in the range of MIC 2.88-8.14 μg/mL and it is a comparable activity of streptomycin (MIC = 3.14-7.43 μg/mL). Most of the compounds provide potent activity against E. coli which is equivalent to streptomycin (MIC = 3.14 μg/mL). The title compounds have been docked into the active site of E. coli DNA gyrase A enzyme to ensure the binding mode and the results demonstrate that a few compounds show better binding energies with enzyme than that of standard, streptomycin and associated with antibacterial activity. [ABSTRACT FROM AUTHOR]