[Synthesis and properties of the N-acyl derivatives of carminomycin and rubomycin].
Synthesis of N-acetylcarminomycin (III) is performed for the first time and the method of selective aminoacylation of 3'-NH2 group of carminomycin (I) and rubomycin (II) is elaborated. The method is based on interaction of N alpha-protected amino acid activated with respect to the carboxyl group with one of the antibiotics followed by removal of the protective group under mild conditions. O-Nitrophenylsulphenyl group (NPS) is used as the protective agent. In case of rubomycin (II), N alpha-NPS-amino acid is attached with the carbodiimide method. In case of carminomycin (I) the similar reaction proceeds inconsistently and carminomycin is acylated with the method of activated ethers and the use of N-hydroxysuccinimide ether of N alpha-NPS-protected amino acid. The following substances were prepared: N-(N alpha-NPS-D-phenylalanyl)-carminomycin (IVa), n-(n alpha-NPIa) and N-(N alpha-NPS-L-alanyl)-rubomycin (VIIa). Removal of NPS-group is performed under mild conditions (2 equiv. HCl in acetone, 20 degrees C, 2 min) without significant destruction of the antibiotic glucoside bond and results in formation of respective water-soluble hydrochlorides of N-aminoacyl derivatives of carminomycin and rubomycin (IV-VII). Teh structures of the new compounds are confirmed by the analytical and spectral data (Rf, [alpha] D, IR-, UV- and VO-, PMR-spectra, elementary analysis) and their chemical transformations. Antimicrobial activity of N-acetylcarminomycin (III) and water-soluble hydrochlorides of carminomycin and rubomycin derivatives (IV-VII) against Bas. mycoides is 5-10% of that of the respective initial antibiotics (I) and (II).
D000215:Acylation; D002360:Carubicin / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D003630:Daunorubicin / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D002360:Carubicin; D003630:Daunorubicin
Sintez i svoĭstva nekotorykh N-atsil'nykh proizvodnykh karminomitsina i rubomitsina.