Open AccessDesign, Synthesis, and Monoamine Oxidase Inhibitory Activity of (+)-Cinchonaminone and Its Simplified Derivatives
Author(s) -
Yuta Sato,
Naoko Oyobe,
Takao Ogawa,
Sayo Suzuki,
Hiroshi Aoyama,
Tomonori Nakamura,
Hiromichi Fujioka,
Satoshi Shuto,
Mitsuhiro Arisawa
Publication year - 2021
Publication title -
acs medicinal chemistry letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.065
H-Index - 66
ISSN - 1948-5875
DOI - 10.1021/acsmedchemlett.1c00310
Subject(s) - enantiomer , monoamine oxidase , enantioselective synthesis , piperidine , inhibitory postsynaptic potential , chemistry , stereochemistry , indole test , indole alkaloid , monoamine neurotransmitter , tryptamines , alkaloid , enzyme , biochemistry , serotonin , biology , receptor , catalysis , neuroscience , tryptamine
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.