ADMET and DMPK, Vol. 2 No. 3, 2014.
Original scientific paper
https://doi.org/10.5599/admet.2.3.47
Electrochemical Synthesis, Structure Elucidation and Antibacterial Evaluation of 9a-aza-9a-chloro-9a-homoerythromycin A
Zoran Mandić
; University of Zagreb, Faculty of Chemical Engineering and Technology, Marulićev trg 19, HR-10000, Zagreb, Croatia
Gorjana Lazarevski
; Ilica 134a, HR-10000, Zagreb, Croatia
Zlatko Weitner
; Hrvatskih iseljenika 1, HR-10000, Zagreb, Croatia
Predrag Novak
; University of Zagreb, Faculty of Science, Department of Chemistry, Horvatovac 102a, HR-10000, Zagreb, Croatia
Nataša Maršić
; Hraste and Partners Attorneys at Law, Ribnjak 40, HR-10000, Zagreb, Croatia
Ana q Budimir
; University of Zagreb, School of Medicine, Salata 3, 10 000 Zagreb
Abstract
Electrochemical synthesis, structure elucidation and antibacterial evaluation of 9a-aza-9a-chloro-9a-homoerythromycin A were carried out. It was found that the anodic oxidation of 9a-aza-9a-homoerythromycin A via electrogenerated reactive chlorine species leads to the chlorination of lactam nitrogen in high yield provided the pH of the reaction mixture is maintained above 3. NOESY spectra reveal the existence of the mixture of two conformational families in the solution, the "folding-out" conformer being slightly more abundant comparing to 9a-Aza-9a-homoerythromycin A. The chlorine substitution of lactam hydrogen resulted in improved antimicrobial potency against Sreptococcus pyogenes PSCB0542, Moraxella catarrhalis ATCC 25238, Haemophilus influenzae ATCC 49247 and Enteroccocus faecalis ATCC 29212.
Keywords
azithromycin; electrochemical chlorination; N-chloro lactam; antbacterial activity
Hrčak ID:
127041
URI
Publication date:
16.9.2014.
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