Electrochemical Synthesis, Structure Elucidation and Antibacterial Evaluation of 9a-aza-9a-chloro-9a-homoerythromycin A
| Autor: | Predrag Novak, Zlatko Weitner, Zoran Mandić, Ana Budimir, Gorjana Lazarevski, Nataša Maršić |
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| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
Hydrogen
Chemistry lcsh:RM1-950 Medicine (miscellaneous) chemistry.chemical_element Antimicrobial Electrochemistry Combinatorial chemistry chemistry.chemical_compound lcsh:Therapeutics. Pharmacology Chemistry (miscellaneous) Yield (chemistry) azithromycin electrochemical chlorination N-chloro lactam antbacterial activity Lactam Chlorine polycyclic compounds Organic chemistry Pharmacology (medical) General Pharmacology Toxicology and Pharmaceutics Conformational isomerism Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | ADMET and DMPK Volume 2 Issue 3 ADMET and DMPK, Vol 2, Iss 3, Pp 179-184 (2014) |
| ISSN: | 1848-7718 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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