Scalable synthesis and antibacterial evaluation of 2-(3-(N-(substituted phenyl)sulfamoyl)ureido)benzothiazoles

Arch Pharm (Weinheim). 2019 Aug;352(8):e1800341. doi: 10.1002/ardp.201800341. Epub 2019 Jun 27.

Abstract

A new series of 2-(3-(N-(substituted phenyl)sulfamoyl)ureido)benzothiazoles was synthesized via a one-pot efficient and scalable method, involving the condensation of 2-aminobenzothiazoles derivatives, substituted anilines, and chlorosulfonyl isocyanate. The products were obtained in good yield with a simple workup, and their structures were confirmed from their spectral analyses. The synthesized compounds were further screened for their antibacterial activity against Gram-positive and Gram-negative pathogenic strains. The molecules show promising activity in the MIC value range of 2-0.25 µg/ml against selected bacterial strains, especially against nonfermentative carbapenem-resistant bacteria (Pseudo VIM-2 and Acinetobacter baumanni).

Keywords: 2-aminobenzothiazol; MDR bacteria; antibacterial activity; scalable synthesis; sulfamoylurea.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Benzothiazoles / chemical synthesis
  • Benzothiazoles / chemistry
  • Benzothiazoles / pharmacology*
  • Dose-Response Relationship, Drug
  • Gram-Negative Bacteria / drug effects*
  • Gram-Positive Bacteria / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Benzothiazoles

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