8-Azatetracyclines: synthesis and evaluation of a novel class of tetracycline antibacterial agents

J Med Chem. 2011 Mar 10;54(5):1511-28. doi: 10.1021/jm1015389. Epub 2011 Feb 8.

Abstract

A novel series of fully synthetic 8-azatetracyclines was prepared and evaluated for antibacterial activity. Compounds were identified that overcome both efflux (tet(K)) and ribosomal protection (tet(M)) tetracycline resistance mechanisms and are active against Gram-positive and Gram-negative organisms. Two compounds were identified that exhibit comparable efficacy to marketed tetracyclines in in vivo models of bacterial infection.

MeSH terms

  • Administration, Oral
  • Animals
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Aza Compounds / chemical synthesis*
  • Aza Compounds / chemistry
  • Aza Compounds / pharmacology
  • Biological Availability
  • Escherichia coli Infections / prevention & control
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Injections, Intravenous
  • Mice
  • Microbial Sensitivity Tests
  • Rats
  • Rats, Sprague-Dawley
  • Sepsis / prevention & control
  • Streptococcal Infections / prevention & control
  • Structure-Activity Relationship
  • Tetracycline Resistance / drug effects
  • Tetracyclines / chemical synthesis*
  • Tetracyclines / chemistry
  • Tetracyclines / pharmacology

Substances

  • 6-demethyl-6-deoxy-7-(dimethylamino)-8-azatetracycline
  • 7-chloro-6-demethyl-6-deoxy-9-((3-(dimethylamino)-2,2-dimethylpropyl)amino)-8-azatetracycline
  • Anti-Bacterial Agents
  • Aza Compounds
  • Tetracyclines