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3-O-Acyl Derivatives of Bridged-15-Membered Azalides: Synthesis, Structural Determination and Antibacterial Activity

Andrea Fajdetić
Gabrijela Kobrehel
Gorjana Lazarevski
Vlado Štimac
Stjepan Mutak

Puni tekst: engleski, pdf (159 KB) str. 301-312 preuzimanja: 309* citiraj
APA 6th Edition
Fajdetić, A., Kobrehel, G., Lazarevski, G., Štimac, V. i Mutak, S. (2005). 3-O-Acyl Derivatives of Bridged-15-Membered Azalides: Synthesis, Structural Determination and Antibacterial Activity. Croatica Chemica Acta, 78 (2), 301-312. Preuzeto s https://hrcak.srce.hr/26
MLA 8th Edition
Fajdetić, Andrea, et al. "3-O-Acyl Derivatives of Bridged-15-Membered Azalides: Synthesis, Structural Determination and Antibacterial Activity." Croatica Chemica Acta, vol. 78, br. 2, 2005, str. 301-312. https://hrcak.srce.hr/26. Citirano 05.04.2020.
Chicago 17th Edition
Fajdetić, Andrea, Gabrijela Kobrehel, Gorjana Lazarevski, Vlado Štimac i Stjepan Mutak. "3-O-Acyl Derivatives of Bridged-15-Membered Azalides: Synthesis, Structural Determination and Antibacterial Activity." Croatica Chemica Acta 78, br. 2 (2005): 301-312. https://hrcak.srce.hr/26
Harvard
Fajdetić, A., et al. (2005). '3-O-Acyl Derivatives of Bridged-15-Membered Azalides: Synthesis, Structural Determination and Antibacterial Activity', Croatica Chemica Acta, 78(2), str. 301-312. Preuzeto s: https://hrcak.srce.hr/26 (Datum pristupa: 05.04.2020.)
Vancouver
Fajdetić A, Kobrehel G, Lazarevski G, Štimac V, Mutak S. 3-O-Acyl Derivatives of Bridged-15-Membered Azalides: Synthesis, Structural Determination and Antibacterial Activity. Croatica Chemica Acta [Internet]. 2005 [pristupljeno 05.04.2020.];78(2):301-312. Dostupno na: https://hrcak.srce.hr/26
IEEE
A. Fajdetić, G. Kobrehel, G. Lazarevski, V. Štimac i S. Mutak, "3-O-Acyl Derivatives of Bridged-15-Membered Azalides: Synthesis, Structural Determination and Antibacterial Activity", Croatica Chemica Acta, vol.78, br. 2, str. 301-312, 2005. [Online]. Dostupno na: https://hrcak.srce.hr/26. [Citirano: 05.04.2020.]

Sažetak
The synthesis, structural determination and biological evaluation of 15-membered azalides acylated at the C-3 position are described. 3-Descladinosyl-9a,l1-cyclic carbamate of the 9a-aza- 9a-homoerythromycin A and their 12-O-alkyl derivatives were synthesized via acidic hydrolysis of adequate 3-cladinosyl analogues. Protections of 2'-hydroxyl group were performed to furnish starting compounds for acylation of the C-3-hydroxyl group. After deprotection various 3-O-acyl derivatives were obtained and their structures confirmed by spectroscopic methods (IR, MS, NMR). The new compounds were evaluated in vitro against a panel of Gram-positive and Gram-negative bacteria and their activities compared with those of parent derivatives. The 3-O-acyl derivatives exhibited improved antibacterial activity, but it was lower than by standard macrolides.

Ključne riječi
azalides; synthesis; acylation; NMR spectroscopy

Hrčak ID: 26

URI
https://hrcak.srce.hr/26

[hrvatski]

Posjeta: 653 *