Naslov
Synthesis and Antibacterial Activity of Isomeric 15- Membered Azalides

Autori
Alihodžić, Sulejman ; Fajdetić, Andreja ; Kobrehel, Gabrijela ; Lazarevski, Gorjana ; Mutak, Stjepan ; Pavlović, Dražen ; Štimac, Vlado ; Čipčić, Hana ; Eraković, Vesna ; Maršić, Nataša ; Schoenfeld, Wolfgang

Izvornik
Journal of antibiotics (0021-8820) 59 (2006), 12; 753-769

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
azalide; ketolide; acylide; antibacterial activity; structure-activity relationship

Sažetak
A series of 3-keto and 3-O-acyl derivatives of both 6-O-alkyl-8a-aza-8a-homoerythromycin A and 6- O-alkyl-9a-aza-9a-homo-erythromycin A were synthesised and tested against gram-positive and gram-negative bacteria. Derivatives of 8a-aza-8a- homoerythromycin A have potent antibacterial activity against not only azithromycin-susceptible strains, but also efflux (M) and inducible macrolide-lincosamide-streptogramin (iMLSB) resistant Gram-positive pathogens, while the corresponding 9a-isomers were less active. Introduction of an additional ring such as 11, 12- cyclic carbonate reduced antibacterial activity of both series. 3-Keto and 3-O-(4-nitrophenyl)acetyl derivatives of 6-O-methyl-8a-aza-8a-homo- erythromycin A show typical macrolide pharmacokinetics in preliminary in vivo studies in mice, and their in vivo efficacy is demonstrated.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija

POVEZANOST RADA