Synthesis and biological activity of O56-substituted carboxyesters and carboxamides of teicoplanin aglycone.
A series of O56-substituted carboxyester or carboxyamide derivatives of deglucoteicoplanin (TD) was prepared by condensation of the 56-hydroxyl function with various alkylating agents of general formula RBr, where R represents functional groups with different physico-chemical properties. The modifications at position 56 influenced the antimicrobial activity of the new derivatives; activity depended on the structure of various R groups, their ionic properties, and their steric hindrance. The activity of the new compounds did not show any significant improvement when compared with TD. The physico-chemical and antibacterial properties of the synthesized compounds are reported.
Seneci
P
P
Marion Merrell Dow Research Institute, Lepetit Research Center, Gerenzano (VA), Italy.
Trani
A
A
Ferrari
P
P
Scotti
R
R
Ciabatti
R
R
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship; D017334:Teicoplanin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D017334:Teicoplanin; C063101:teicoplanin aglycone