ERYTHROMYCIN SERIES: XII. ANTIBACTERIAL IN VITRO EVALUATION OF 10-DIHYDRO-10-DEOXO-11-AZAERYTHROMYCIN A: SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIP OF ITS ACYL DERIVATIVES

Antibacterial in vitro evaluation of 10-dihydro-10-deoxo-11-azaerythromycin A† (5), the new 15-membered semi-synthetic macrolide antibiotic with nitrogen as additional atom in the aglycone ring of erythromycin A (1), was reported. Although amine (5) and its 13, 14-cyclic carbonate (14) were less active than 1 against erythromycin-sensitive Staphylococcus aureus strains they showed advantageous properties against Gram-negative test organisms and clinical isolates. Also, a large number of acyl derivatives of 5 were synthesized and evaluated. N-11 monoacyl compounds exhibited 2 to 50 times lower in vitro antibacterial efficacy than the parent amine (5).