Expedient on-resin synthesis of peptidic benzimidazoles

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

卷:28

Article

Bird, Michael J.¹  Silvestri, Anthony P.¹  Dawson, Philip E.¹ 

[1] Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA

关键词: Peptide benzimidazoles;    SPPS;    Benzimidazoles;    Peptide therapeutics;    Antimicrobials;    Antifungals;    Anthelmintics;   

DOI  :  10.1016/j.bmcl.2018.04.062

来源: Elsevier

【 摘 要 】

The benzimidazole moiety is a ubiquitous pharmacophore present in numerous anthelmintic, antibacterial, antiviral, antineoplastic, and antifungal drugs. While the polypharmacology of this heterocycle has spurred the development of numerous solution-phase syntheses, only a handful of disparate and inefficient methods detailing its synthesis on-resin have been reported. Here we report the concise and expedient syntheses of internal and C-terminal peptidic benzimidazoles - an emerging class of peptide deformylase (PDF)-inhibiting antimicrobials. This method benefits from being performed wholly on solid-phase at room temperature resulting in minimal purification and tolerance of temperature-sensitive functionality. (C) 2018 Published by Elsevier Ltd.

【 授权许可】

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