An Efficient Synthesis of 3-Alkylpyridine Alkaloids Enables Their Biological Evaluation

• Type of Material: Article
• Authors: Anna R Kaplan, Emory University; Cassandra L Schrank, Emory University; William Wuest, Emory University
• Language: English
• Date: 2021-04-14
• Publisher: WILEY-V C H VERLAG GMBH
• Publication Version: Author Accepted Manuscript (After Peer Review)
• Copyright Statement: © 2021 Wiley‐VCH GmbH
• Final Published Version (URL): http://dx.doi.org/10.1002/cmdc.202100134
• Title of Journal or Parent Work: CHEMMEDCHEM
• Volume: 16
• Issue: 16
• Start Page: 2487
• End Page: 2490
• Keywords: Life Sciences & Biomedicine; hydroarylation; Science & Technology; antimicrobial; Pharmacology & Pharmacy; haliclocyclins; Chemistry, Medicinal; MRSA; quaternary ammonium compounds

Abstract

3-Alkylpyridine alkaloids (3-APAs) isolated from the arctic sponge Haliclona viscosa are a promising group of bioactive marine alkaloids. However, due to limited bioavailability, investigations of their bioactivity have been hampered. Additionally, synthesis of a common intermediate requires the use of protecting groups and harsh conditions. In this work, we developed a simple and concise two-step route to nine different natural and synthetic haliclocyclins. These compounds displayed modest antibiotic activity against several Gram-positive bacterial strains.