Synthesis of 17-membered azalides from a 16-membered macrolide utilizing amide-selective silane reduction

Abstract

Novel 17-membered azalides of N-methylated amine type were synthesized and their antibacterial activity was evaluated.

Synthesis, Antibacterial, and Anticancer Evaluation of Novel Spiramycin-Like Conjugates Containing C(5) Triazole Arm

“…Up to now, many modifications, both within spiramycin and leucomycin groups, have been proposed and tested to obtain comparably or more active alternative agents able to fight the growing bacterial resistance. Most of the modifications were related to transformation of the aldehyde via reduction, nucleophilic addition, − hydroxyl groups within the aglycone and saccharides parts via etherification, acylation, or sulphonylation, , diene moiety via epoxidation, reduction, Diels–Alder reaction, or metathesis with contraction of the lactone ring, − forosamine and/or mycaminose N -oxidation or N -substitution, , and incorporation of the nitrogen into the lactone macrocyclic ring. − An interesting platform to synthesis and drug discovery among the group of macrolide lactone antibiotics has been recently proposed by Seiple et al Convenient synthetic strategy leading to obtaining of new chemical entities characterized by attractive biological properties is the use of click chemistry reactions. − An interesting approach to modification of these structurally complexed macrolides, in view of their known mechanism of action, has been described by Omura and Sharpless et al They proposed the functionalization of terminal hydroxyls of mycarose saccharide with alkyne followed by conversion into respective triazole moieties via Fokin–Huisgen cycloadditions. However, as a result of this transformation, the obtained derivatives were significantly less active than the parent leucomycin due to the presence of a too long arm at C(5) of the aglycone.…”