Chemical modification of spiramycins. V. Synthesis and antibacterial activity of 3'- or 4''-de-N-methylspiramycin I and their N-substituted derivatives.
The 3'- and 4''-de-N-methylspiramycins were synthesized selectively, and then were converted to various N-substituted derivatives. 4''-De-N-methyl derivatives were more active than 3'-de-N-methyl ones. Among the derivatives, 4''-N-Fmoc-glycyl and 4''-N-benzyl-4''-de-N-methylspiramycin I were the most active in vitro, and were comparable to spiramycin I. 4''-De-N-methylspiramycin I was about half as active as spiramycin I in vivo.
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001665:Binding Sites; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D007933:Leucomycins; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008826:Microbial Sensitivity Tests; D012270:Ribosomes / Q000378:metabolism
D000900:Anti-Bacterial Agents; D007933:Leucomycins