Abstract
We describe herein the synthesis and biological activity of two indoloazepines that are structurally related to the marine sponge metabolite hymenialdisine. The natural product hymenialdisine was found to be a potent inhibitor of interleukin-2 (IC(50) = 2.4 microM) and tumor necrosis factor alpha (IC(50) = 1.4 microM) production. One of the hymenialdisine derived indoloazepines was found to also inhibit interleukin-2 (IC(50) = 3.5 microM) and tumor necrosis factor alpha (IC(50) = 8.2 microM) production.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
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Anti-Inflammatory Agents, Non-Steroidal / chemistry
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Anti-Inflammatory Agents, Non-Steroidal / pharmacology
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Azepines / chemical synthesis*
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Azepines / chemistry
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Azepines / pharmacology
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Cell Line, Tumor
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Crystallography, X-Ray
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Cytokines / antagonists & inhibitors*
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Cytokines / biosynthesis
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Humans
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Indoles / chemical synthesis
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Indoles / chemistry
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Indoles / pharmacology
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Interleukin-2 / antagonists & inhibitors
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Interleukin-2 / biosynthesis
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Molecular Structure
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Pyrroles / chemical synthesis*
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Pyrroles / chemistry
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Pyrroles / pharmacology
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Structure-Activity Relationship
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Tumor Necrosis Factor-alpha / antagonists & inhibitors
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Tumor Necrosis Factor-alpha / biosynthesis
Substances
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Anti-Inflammatory Agents, Non-Steroidal
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Azepines
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Cytokines
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Indoles
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Interleukin-2
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Pyrroles
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Tumor Necrosis Factor-alpha
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hymenialdisine