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

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 require...

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Bibliographic Details
Published in:ChemMedChem
Main Authors: Kaplan, Anna R., Schrank, Cassandra L., Wuest, William M.
Other Authors: National Institutes of Health
Format: Article in Journal/Newspaper
Language:English
Published: Wiley 2021
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Online Access:http://dx.doi.org/10.1002/cmdc.202100134
https://onlinelibrary.wiley.com/doi/pdf/10.1002/cmdc.202100134
https://onlinelibrary.wiley.com/doi/full-xml/10.1002/cmdc.202100134
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Summary: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.