title: Novel 8a-aza-8a-homoerythromycin--4''-(3-substituted-amino)propionates with broad spectrum antibacterial activity.
abstract: Fifteen-membered 8a-aza-8a-homoerythromycins derived from either erythromycin or clarithromycin have been acylated to form 4''-O-propenoyl derivative. These functionalized analogues underwent Michael reaction with primary or secondary amines to afford novel 8a-aza-8a-homoerythromycin-4''-(3-substituted-amino)propionates. This preparative sequence was adapted so that analogues could be made by parallel synthesis. Among them, 4-quinolone derivatives show particularly good antibacterial potency against macrolide resistant bacteria, comparable or better than azithromycin and telithromycin.
authors.affiliation: GlaxoSmithKline Research Centre, Zagreb, Prilaz baruna Filipovića 29, HR-10 000 Zagreb, Croatia. antun.z.hutinec@gsk.com
authors.forename: Antun
authors.initials: A
authors.lastname: Hutinec
authors.forename: Marko
authors.initials: M
authors.lastname: Derek
authors.forename: Gorjana
authors.initials: G
authors.lastname: Lazarevski
authors.forename: Vitomir
authors.initials: V
authors.lastname: Sunjić
authors.forename: Hana Cipcić
authors.initials: HC
authors.lastname: Paljetak
authors.forename: Sulejman
authors.initials: S
authors.lastname: Alihodzić
authors.forename: Vesna
authors.initials: V
authors.lastname: Eraković Haber
authors.forename: Miljenko
authors.initials: M
authors.lastname: Dumić
authors.forename: Natasa
authors.initials: N
authors.lastname: Marsić
authors.forename: Stjepan
authors.initials: S
authors.lastname: Mutak
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000145:classification / Q000187:drug effects; D004917:Erythromycin / Q000031:analogs & derivatives* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests
chemical_list: D000900:Anti-Bacterial Agents; D004917:Erythromycin