Synthesis of two and antibacterial activity of one novel oxime ether derivatives of erythromycin A.
The synthesis of novel erythromycin A 9-O-(2-ethenesulfony-ethyl)-oxime and erythromycin A 9-O-(3-oxo-butyl)-oxime from erythromycin A (EA) by the Michael reaction is described and to describe the effects of transformation of ketone in position 9 of EA to an oxime ether. This transformation occurred in a single step without protecting of any functional moiety of erythromycin oxime and zero waste manner in good yield. The antibacterial screen of EA 9-O-(2-ethenesulfony-ethyl)-oxime is also reported.
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003353:Corynebacterium diphtheriae / Q000187:drug effects; D004917:Erythromycin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects; D004987:Ethers / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D010091:Oximes / Q000138:chemical synthesis* / Q000494:pharmacology; D013210:Staphylococcus / Q000187:drug effects; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D004987:Ethers; D010091:Oximes; D004917:Erythromycin