title: 3-Keto-11,12-carbazate derivatives of 6-O-methylerythromycin A synthesis and in vitro activity.
abstract: The 11,12-cyclic carbazate of 3-keto-6-O-methylerythromycin A (4) was prepared. This compound shows in vitro antibacterial activity comparable to erythromycin A (1) against erythromycin-susceptible organisms and increased activity against some erythromycin-resistant organisms. Using 4 as a lead, a series of analogues was prepared by acylation or alkylation of the carbazate nitrogen. Several of the N-alkylated derivatives showed dramatically improved antibacterial activity against both susceptible and resistant organisms as compared to erythromycin A.
authors.affiliation: Abbott Laboratories, Abbott Park, Illinois 60064, U.S.A.
authors.forename: G
authors.initials: G
authors.lastname: Griesgraber
authors.forename: Y S
authors.initials: YS
authors.lastname: Or
authors.forename: D T
authors.initials: DT
authors.lastname: Chu
authors.forename: A M
authors.initials: AM
authors.lastname: Nilius
authors.forename: P M
authors.initials: PM
authors.lastname: Johnson
authors.forename: R K
authors.initials: RK
authors.lastname: Flamm
authors.forename: R F
authors.initials: RF
authors.lastname: Henry
authors.forename: J J
authors.initials: JJ
authors.lastname: Plattner
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004917:Erythromycin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D048628:Ketolides; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: C100405:3-keto-6-O-methylerythromycin A 11,12-cyclic carbazate; D000900:Anti-Bacterial Agents; D048628:Ketolides; D004917:Erythromycin