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Design,Synthesis, and Monoamine Oxidase Inhibitory Activity of (+)-Cinchonaminone and Its Simplified Derivatives |
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| Authors: | Yuta Sato Naoko Oyobe Takao Ogawa Sayo Suzuki Hiroshi Aoyama Tomonori Nakamura Hiromichi Fujioka Satoshi Shuto Mitsuhiro Arisawa |
| Institution: | †Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan;‡Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12, Nishi 6, Kita-ku, Sapporo 060-0808, Japan;§Graduate School of Pharmaceutical Sciences, Keio University, Shibakoen 1-5-30, Minato-ku, Tokyo 105-8512, Japan |
| 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. |
| Keywords: | Total synthesis indole alkaloid absolute structure determination monoamine oxidase (MAO) inhibitory activity structurally simplified derivatives |