Synthesis, In Vitro Anti-Microbial Analysis and Molecular Docking Study of Aliphatic Hydrazide-Based Benzene Sulphonamide Derivatives as Potent Inhibitors of α-Glucosidase and Urease

Molecules. 2022 Oct 21;27(20):7129. doi: 10.3390/molecules27207129.

Abstract

A unique series of sulphonamide derivatives was attempted to be synthesized in this study using a new and effective method. All of the synthesized compounds were verified using several spectroscopic methods, including FTIR, 1H-NMR, 13C-NMR, and HREI-MS, and their binding interactions were studied using molecular docking. The enzymes urease and α-glucosidase were evaluated against each derivative (1-15). When compared to their respective standard drug such as acarbose and thiourea, almost all compounds were shown to have excellent activity. Among the screened series, analogs 5 (IC50 = 3.20 ± 0.40 and 2.10 ± 0.10 µM) and 6 (IC50 = 2.50 ± 0.40 and 5.30 ± 0.20 µM), emerged as potent molecules when compared to the standard drugs acarbose (IC50 = 8.24 ± 0.08 µM) and urease (IC50 = 7.80 ± 0.30). Moreover, an anti-microbial study also demonstrated that analogs 5 and 6 were found with minimum inhibitory concentrations (MICs) in the presence of standard drugs streptomycin and terinafine.

Keywords: SAR and molecular docking; anti-microbial; anti-urease; sulphonamide; synthesis; α-glucosidase.

MeSH terms

  • Acarbose / pharmacology
  • Benzene
  • Benzene Derivatives
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Glycoside Hydrolase Inhibitors / chemistry
  • Glycoside Hydrolase Inhibitors / pharmacology
  • Hydrazines
  • Molecular Docking Simulation
  • Molecular Structure
  • Streptomycin
  • Structure-Activity Relationship
  • Sulfanilamide
  • Thiourea / chemistry
  • Urease*
  • alpha-Glucosidases* / metabolism

Substances

  • alpha-Glucosidases
  • Urease
  • Benzene
  • Hydrazines
  • Benzene Derivatives
  • Acarbose
  • Thiourea
  • Sulfanilamide
  • Streptomycin
  • Enzyme Inhibitors
  • Glycoside Hydrolase Inhibitors