Abstract
The new ureas and thioureas of 15-membered azalides, N″-substituted 9a-( N′-carbamoyl-γ-aminopropyl) ( 4), 9a-( N′-thiocarbamoyl-γ-aminopropyl) ( 6), 9a-[ N′-(β-cyanoethyl)- N′-(carbamoyl-γ-aminopropyl)] ( 8) and 9a-[ N′-(β-cyanoethyl)- N′-(thiocarbamoyl-γ-aminopropyl)] ( 10) of 9-deoxo-9-dihydro-9a-aza-9a-homoerythromycin A ( 2), were synthesized and structurally characterized by NMR and IR spectroscopic methods and mass spectrometry. The new compounds were evaluated in vitro against a panel of erythromycin susceptible and erythromycin-resistant Gram-positive and Gram-negative bacterial strains. These compounds displayed an excellent overall antibacterial in vitro activity against erythromycin sensitive Gram-positive strains, Streptococcus pneumoniae, Streptococcus pyogenes, Staphylococcus aureus, and good against negative strains, Moraxella catarrhalis and Haemophilus influenzae. In addition, several ureas with naphthyl substituents ( 4f, 4g, 4h) showed better activity in comparison to azithromycin against inducible resistant S. pyogenes. Ureas with naphthyl substituents 4g, 4h and thiourea 8h displayed moderate activity against constitutively resistant S. pneumoniae.
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