Synthesis of natural product-like polyprenylated phenols and quinones: Evaluation of their neuroprotective activities.

Twenty-seven natural product-like polyprenylated phenols and quinones were synthesized and their neuroprotective activity was tested using human monoamine oxidase B (MAO-B) and SH-SY5Y cells. Eight compounds inhibited MAO-B (IC50 values < 25 μM) and the inhibition mode and molecular docking of two (8c and 16c) were investigated. Compounds inhibiting MAO-B activity were additionally tested for their ability to protect SH-SY5Y cells from peroxide injury. Three derivatives (3c, 8c and 16c) exhibited both MAO-B inhibitory and neuroprotective activity. A structure activity-relationship study showed that a phenolic hydroxyl group and a longer side chain are important for both activities. Copyright © 2019 Elsevier Ltd. All rights reserved.

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Hitoshi Kamauchi, Takumi Oda, Kanayo Horiuchi, Koichi Takao, Yoshiaki Sugita. Synthesis of natural product-like polyprenylated phenols and quinones: Evaluation of their neuroprotective activities. Bioorganic & medicinal chemistry. 2020 Jan 01;28(1):115156

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PMID: 31740200

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