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Nauchni Trudove Na Visshiia Meditsinski... 1957
Topics: Oximes; Phosgene; Therapies, Investigational
PubMed: 13526752
DOI: No ID Found -
European Journal of Medicinal Chemistry Aug 2008In a study of the importance of a basic amino function in erythromycin derived antibiotics, N'-demethylazithromycin 2',3'-carbamate-11,12-carbonate has been prepared in...
In a study of the importance of a basic amino function in erythromycin derived antibiotics, N'-demethylazithromycin 2',3'-carbamate-11,12-carbonate has been prepared in six steps from (9E)-erythromycin A 9-oxime. Reactions with phosgene provided a cyclic carbonate from the vicinal 11,12-diol, and a cyclic 2',3'-carbamate from the vicinal dimethylamino-alcohol moiety of the desosamine sugar. Further transformations provided N,N'-di(demethyl)azithromycin 2',3'-carbamate-11,12-carbonate N-methylated at position 9a. The activity of the oxime was reduced in comparison with the parent azithromycin. Hence the N,N-dimethylamino group in the desosamine sugar is important for good antibacterial activity. The course of the phosgene reactions has been verified by an X-ray analysis.
Topics: Anti-Bacterial Agents; Azithromycin; Carbamates; Cyclization; Microbial Viability; Models, Molecular; Molecular Structure; Structure-Activity Relationship
PubMed: 18045746
DOI: 10.1016/j.ejmech.2007.10.013