4''-O-(omega-Quinolylamino-alkylamino)propionyl derivatives of selected macrolides with the activity against the key erythromycin resistant respiratory pathogens

Bioorganic & Medicinal Chemistry
A FajdetićR Spaventi

Abstract

Four macrolides-6-O-methyl-8a-aza-8a-homoerythromycin, clarithromycin, azithromycin and azithromycin 11,12-cyclic carbonate, have been selected for the construction of a series of new quinolone derivatives. The quinolone moiety is connected to the macrolide scaffold via a diaminoaklyl 4''-O-propionyl ester chain of varying length. At the terminus the linker is attached via one of the nitrogen atoms in the linker at C(6) or C(7) of the quinolone. Many of compounds described, particularly clarithromycin derivative 37, and azithromycin derivatives 48 and 55, exhibited excellent antibacterial activity against a wide range of clinically relevant macrolide-resistant organisms, with profiles superior to that of telithromycin, an enhanced spectrum ketolide.

References

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Citations

Feb 28, 2013·Expert Opinion on Drug Discovery·Zhi-Xiong RuanWei-Min Chen
Nov 9, 2010·Bioorganic & Medicinal Chemistry·Dražen PavlovićStjepan Mutak
Nov 4, 2011·Bioorganic & Medicinal Chemistry·Samra KapićSulejman Alihodžić
Sep 7, 2016·Antibiotics·Dubravko Jelić, Roberto Antolović
Jun 30, 2016·Antimicrobial Agents and Chemotherapy·Hana Čipčić PaljetakVesna Eraković Haber
Nov 12, 2018·Journal of Industrial Microbiology & Biotechnology·Je Won Park, Yeo Joon Yoon
Oct 14, 2018·The Journal of Antibiotics·Anna N TevyashovaIlya A Osterman

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