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

• Published in: Journal of antibiotics Vol. 40; no. 7; pp. 1006 - 1015
• Main Authors: DJOKIC, SLOBODAN, KOBREHEL, GABRIJELA, LAZAREVSKI, GORJANA
• Format: Journal Article
• Language: English
• Published: Tokyo JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 1987; Japan Antibiotics Research Association
• Subjects: Anti-Bacterial Agents - pharmacology; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Erythromycin - analogs & derivatives; Erythromycin - pharmacology; Exact sciences and technology; Gram-Negative Bacteria - drug effects; Magnetic Resonance Spectroscopy; Organic chemistry; Preparations and properties; Structure-Activity Relationship; Staphylococcus aureus; Structure activity relation; Aminoglycoside; Lactone; Mass spectrum; Antibacterial agent; NMR spectrum; Oxygen nitrogen heterocycle; Macrocycle
• ISSN: 0021-8820; 1881-1469
• DOI: 10.7164/antibiotics.40.1006

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).