9a,11-cyclic carbamates of 15-membered azalides

J Antibiot (Tokyo). 1993 Aug;46(8):1239-45. doi: 10.7164/antibiotics.46.1239.

Abstract

The novel 9a,11-cyclic carbamates (13-15) of 9-deoxo-9a-aza-9a-homoerythromycin A (4) have been prepared and characterized by 1H-1H and 1H-13C 2D NMR spectroscopy. When compared to azithromycin (1) or its 6-O-methyl derivative (2), the new bicyclic 15-membered azalides exhibited substantially decreased antibacterial activities in vitro.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azithromycin / analogs & derivatives*
  • Azithromycin / chemistry
  • Azithromycin / pharmacology
  • Bacteria / drug effects*
  • Erythromycin / analogs & derivatives*
  • Erythromycin / chemistry
  • Erythromycin / pharmacology
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Structure-Activity Relationship

Substances

  • Erythromycin
  • Azithromycin
  • 9-deoxy-9a-aza-9a-methyl-9a-homoerythromycin A