Synthesis and activity of novel benzoxazole derivatives of mannopeptimycin glycopeptide antibiotics.
A series of benzoxazole derivatives of the mannopeptimycin glycopeptide antibiotics was synthesized via a novel benzoxazole formation reaction by treating aminophenol of mannopeptimycin-beta with an aldehyde and DDQ in DMF. Some of these derivatives (e.g., 5b, 5d, 5m, and 7b) showed good activity against Gram-(+) bacteria when compared to the parent compound mannopeptimycin-beta.
Sum
Phaik-Eng
PE
Chemical Sciences, Wyeth Research, Pearl River, NY 10965, USA. sump@wyeth.com
How
David
D
Torres
Nancy
N
Newman
Howard
H
Petersen
Peter J
PJ
Mansour
Tarek S
TS
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001583:Benzoxazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002851:Chromatography, High Pressure Liquid; D016983:Enterococcus / Q000187:drug effects; D006020:Glycopeptides; D006094:Gram-Positive Bacteria / Q000187:drug effects*; D007202:Indicators and Reagents; D008826:Microbial Sensitivity Tests; D021241:Spectrometry, Mass, Electrospray Ionization; D013211:Staphylococcus aureus / Q000187:drug effects; D013291:Streptococcus / Q000187:drug effects; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D001583:Benzoxazoles; D006020:Glycopeptides; D007202:Indicators and Reagents; C482471:mannopeptimycin glycopeptide