Synthesis of 2,8-Dioxabicyclo[3.3.1]nonane Derivatives and Their Neuroprotective Activities

Hitoshi Kamauchi; Akifumi Takanashi; Mitsuaki Suzuki; Kouki Izumi; Koichi Takao; Yoshiaki Sugita

doi:10.1248/cpb.c23-00693

Regular Article

Synthesis of 2,8-Dioxabicyclo[3.3.1]nonane Derivatives and Their Neuroprotective Activities

Hitoshi Kamauchi , Akifumi Takanashi, Mitsuaki Suzuki, Kouki Izumi, Koichi Takao, Yoshiaki Sugita

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Keywords: sanctis, 2,8-dioxabicyclo[3.3.1]nonane, lichen, monoamine oxidase, chiral HPLC

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Supplementary material

2024 Volume 72 Issue 1 Pages 56-60

DOI https://doi.org/10.1248/cpb.c23-00693

J-STAGE : cpb 72 2 pp.240-240

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Abstract

Twenty natural-product-like 2,8-dioxabicyclo[3.3.1]nonane derivatives were synthesized and their neuroprotective activities were tested using human monoamine oxidases (MAO) A and B and acetyl and butyryl cholinesterases (ChE). Compound 1s showed inhibitory activity for MAO-A, MAO-B and acetylcholinesterase (AChE) (IC₅₀ values 34.0, 2.3 and 11.0 µM, respectively). The inhibition mode of (−)-1s for MAO-B was investigated. Chiral HPLC of (±)-1s separated the enantiomers and (−)-1s showed MAO-B inhibitory activity. Molecular docking simulation of (−)-1s and MAO-B revealed the binding mode.

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