Abstract
Inspired by aspirin and chalcone, herein, we describe a modular biomimetic strategy to achieve a new class of CF3-bearing benzannulated macrolactams. The key to the success of macrolactams was the utilization of a highly chemoselective Rh(iii)-catalyzed native carboxylic acid-directed C-H alkylation. Moreover, the unique CF3-containing benzannulated macrocycles showed decent immunosuppressive effects on B cells in vitro, including proliferation, activation, and antibody production upon specific stimulation implicating TLR and BCR signaling.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Alkylation
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Animals
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B-Lymphocytes / drug effects*
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B-Lymphocytes / metabolism
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Catalysis
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Immunosuppressive Agents / chemical synthesis
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Immunosuppressive Agents / chemistry
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Immunosuppressive Agents / pharmacology*
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Macrocyclic Compounds / chemical synthesis
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Macrocyclic Compounds / chemistry
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Macrocyclic Compounds / pharmacology*
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Mice
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Molecular Structure
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Receptors, Antigen, B-Cell / metabolism
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Rhodium / chemistry*
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Signal Transduction
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Toll-Like Receptors / metabolism
Substances
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Immunosuppressive Agents
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Macrocyclic Compounds
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Receptors, Antigen, B-Cell
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Toll-Like Receptors
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Rhodium