4-Aminothiazolyl analogs of GE2270 A: design, synthesis and evaluation of imidazole analogs

Bioorg Med Chem Lett. 2011 Jun 1;21(11):3210-5. doi: 10.1016/j.bmcl.2011.04.048. Epub 2011 Apr 21.

Abstract

Imidazole analogs of the antibiotic natural product GE2270 A (1) were designed, synthesized, and evaluated for gram positive bacteria growth inhibition. A recently reported, copper-mediated synthesis was exploited to prepare 4-thiazolyl imidazole analogs of 1. The synthesis described represents a structurally complex, natural product-based application of this recently reported synthetic methodology. In addition, the biological evaluation of the imidazole-based analogs further define the SAR of the 4-aminothiazolyl-based antibacterial template.

MeSH terms

  • Amines / chemical synthesis*
  • Amines / chemistry
  • Amines / pharmacology
  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / pharmacology
  • Copper / chemistry
  • Escherichia coli / drug effects
  • Gram-Positive Bacteria / drug effects*
  • Imidazoles / chemical synthesis
  • Imidazoles / chemistry*
  • Imidazoles / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Peptides, Cyclic / chemistry*
  • Peptides, Cyclic / pharmacology
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry
  • Thiazoles / pharmacology

Substances

  • Amines
  • Anti-Bacterial Agents
  • Imidazoles
  • Peptides, Cyclic
  • Thiazoles
  • Copper
  • GE 2270 A