Design, Synthesis, and Monoamine Oxidase Inhibitory Activity of (+)-Cinchonaminone and Its Simplified Derivatives

Yuta Sato, Naoko Oyobe, Takao Ogawa, Sayo Suzuki, Hiroshi Aoyama, Tomonori Nakamura, Hiromichi Fujioka, Satoshi Shuto, Mitsuhiro Arisawa

Research output: Contribution to journalArticlepeer-review

Abstract

The absolute structure of an indole alkaloid (+)-cinchonaminone by total synthesis of both (+)-cinchonaminone and its enantiomer was determined. The main focus of the study was the enantioselective synthesis of both enantiomers of a chiral cis-3,4-disubstituted piperidine. We also evaluated monoamine oxidase (MAO) inhibitory activities of these enantiomers. Furthermore, its structurally simplified derivatives were synthesized that did not have any chiral center. Two of these derivatives showed stronger MAO inhibitory activities than that of (+)-cinchonaminone.

Original languageEnglish
Pages (from-to)1464-1469
Number of pages6
JournalACS Medicinal Chemistry Letters
Volume12
Issue number9
DOIs
Publication statusPublished - 2021 Sep 9

Keywords

  • Total synthesis
  • absolute structure determination
  • indole alkaloid
  • monoamine oxidase (MAO) inhibitory activity
  • structurally simplified derivatives

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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