Thioureas and isothiouronium salts of the aglycone of teicoplanin. I. Synthesis and biological activity.
A series of thiourea and isothiouronium salt derivatives of the aglycone of teicoplanin was prepared by reaction of the terminal amino group with isothiocyanates, followed by S-alkylation of the thiourea compounds. Unexpectedly, the two classes of derivatives show a similar in vitro antibacterial activity against Gram-positive bacteria. Thiourea compounds, due to the lack of a positively charged N-terminus group, have a 10-fold lower binding constant to Ac-D-Ala-D-Ala, a bacterial cell-wall model, than the parent antibiotic and isothiouronium salt derivatives.
Trani
A
A
Lepetit Research Center, Gerenzano (VA), Italy.
Ferrari
P
P
Pallanza
R
R
Ciabatti
R
R
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002473:Cell Wall / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D004151:Dipeptides / Q000378:metabolism; D006020:Glycopeptides / Q000138:chemical synthesis / Q000494:pharmacology; D007550:Isothiuronium / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship; D017334:Teicoplanin; D013890:Thiourea / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D004151:Dipeptides; D006020:Glycopeptides; C031735:acetylalanylalanine; D007550:Isothiuronium; D017334:Teicoplanin; D013890:Thiourea