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Published on: March 2, 2020
Novel 8a-aza-8a-homoerythromycin--4''-(3-substituted-amino)propionates with broad spectrum antibacterial activity
Antun Hutinec1, Marko Derek, Gorjana Lazarevski
1GlaxoSmithKline Research Centre, Zagreb, Prilaz baruna Filipovića 29, HR-10 000 Zagreb, Croatia. antun.z.hutinec@gsk.com
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.
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