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

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.

SUBMITTER: Sato Y

PROVIDER: S-EPMC8436416 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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

Sato Yuta Y Oyobe Naoko N Ogawa Takao T Suzuki Sayo S Aoyama Hiroshi H Nakamura Tomonori T Fujioka Hiromichi H Shuto Satoshi S Arisawa Mitsuhiro M

ACS medicinal chemistry letters 20210824 9

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 s ...[more]

PMID: 34531955

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