Synthesis and biological investigation of new 4''-malonyl tethered derivatives of erythromycin and clarithromycin.
A new approach to 4''-substituted derivatives of erythromycin and clarithromycin was developed by converting them into corresponding 4''-malonic monoesters. Subsequent carbodiimide coupling with alcohols and amines provided new macrolide derivatives that are capable of binding to 50S ribosomal subunits and inhibiting protein synthesis in cell-free system.
Sherman
Daniel
D
Department of Organic Chemistry, Hebrew University of Jerusalem, Jerusalem 91904, Israel.
Xiong
Liqun
L
Mankin
Alexander S
AS
Melman
Artem
A
D002474:Cell-Free System; D017291:Clarithromycin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000378:metabolism; D004917:Erythromycin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000378:metabolism; D011500:Protein Synthesis Inhibitors / Q000138:chemical synthesis / Q000378:metabolism; D012338:RNA, Ribosomal, 23S / Q000378:metabolism; D012270:Ribosomes / Q000187:drug effects / Q000378:metabolism*
D011500:Protein Synthesis Inhibitors; D012338:RNA, Ribosomal, 23S; D004917:Erythromycin; D017291:Clarithromycin