Abstract
Unprecedented tandem allylic alkylation/intermolecular Michael addition was used in the preparation of novel bicyclic azalides. NMR spectroscopy was used not only to unambiguously determine and characterize the structures of these unexpected products of chemical reaction but also to investigate the effect the rigid bicyclic modification has on the conformation of the whole molecule. Thus, some of the macrolides prepared showed antibacterial activity in the range of well-known antibiotic drug azithromycin.
Highlights
Polyketide macrolides are widely distributed natural products many of which became important medicines in treatment of infectious and neoplastic conditions
Clarithromycin [4] and azithromycin [5] were discovered in the 1980s, followed by ketolides a decade later [6]
In the course of our search for macrolides with novel biological profiles, we investigated the possibilities for regioselective introduction ofaryl moiety at position
Summary
Polyketide macrolides are widely distributed natural products many of which became important medicines in treatment of infectious and neoplastic conditions. In most cases, these compounds contain polyhydroxy macrocyclic lactone glycosylated with one or more sugar moieties [1,2,3]. Erythromycin, a typical representative of this group, was discovered in the 1950s and quickly became commonly used agent in treatment of respiratory and soft tissue infections (Figure 1). The macrolides are studied, or have already found application, as immunomodulators [12], anti-parasitic agents [13,14], or even in treatment of COVID-19 [15]. Some of them even found application in non-medicinal environment, as chiral selectors in liquid chromatography and capillary electrophoresis [16]
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