Synthesis of novel sulfonamide analogs containing sulfamerazine/sulfaguanidine and their biological activities

J Enzyme Inhib Med Chem. 2016 Dec;31(6):1005-10. doi: 10.3109/14756366.2015.1079183. Epub 2015 Aug 31.

Abstract

Sulfamerazine and sulfaguanidine are clenched with p-nitrobenzoyl chloride and the products obtained are reduced to NaxS in ethanol-water. Novel sulfonamides (6a-g and 9a-g) were synthesized by the reaction of these reduced products (4 and 8) with various sulfonyl chlorides (5a-g). The structures of these compounds were characterized using spectroscopic analysis (IR, (1)H-NMR, (13)C-NMR and HRMS) technique. Antimicrobial activity of sulfonamides (3, 4, 7, 8, 6a-g and 9a-g) was evaluated by the agar diffusion method. These compounds showed antimicrobial activity against tested microorganism strains (Gram-positive bacteria, clinic isolate and yeast and mold). Compounds 9d, 9e, 9a, 6d and 6e showed particularly antimicrobial activity against tested Gram-positive (Bacillus cereus and B. subtilis) and Gram-negative (Enterobacter aerogenes) bacteria.

Keywords: Antimicrobial activity; Legionella pneumophila; clinic isolates; sulfaguanidine; sulfamerazine; sulfonamide.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Bacillus / drug effects*
  • Dose-Response Relationship, Drug
  • Enterobacter aerogenes / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Saccharomyces cerevisiae / drug effects*
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Sulfonamides