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Total Synthesis and Monoamine Oxidase Inhibitory Activities of (±)-Entonalactam A and Its Derivatives.


ABSTRACT: The first total synthesis of isoindolinone (±)-entonalactam A (6), originally obtained from the fungus Entonaema sp., was achieved in 14 steps from commercially available 5-bromovanillin via benzophenone intermediates. Isoindolinone, phthalide, and benzophenone analogues of natural products were also synthesized. The monoamine oxidase (MAO) A and B inhibitory activities were tested. The isoindolinone derivative 30 exhibited inhibition of both MAO-A and -B (IC50 = 17.8 and 15.8 μM, respectively).

SUBMITTER: Kamauchi H 

PROVIDER: S-EPMC9670909 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

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Total Synthesis and Monoamine Oxidase Inhibitory Activities of (±)-Entonalactam A and Its Derivatives.

Kamauchi Hitoshi H   Hirata Momoka M   Takao Koichi K   Sugita Yoshiaki Y  

ACS omega 20221104 45


The first total synthesis of isoindolinone (±)-entonalactam A (<b>6</b>), originally obtained from the fungus <i>Entonaema</i> sp., was achieved in 14 steps from commercially available 5-bromovanillin via benzophenone intermediates. Isoindolinone, phthalide, and benzophenone analogues of natural products were also synthesized. The monoamine oxidase (MAO) A and B inhibitory activities were tested. The isoindolinone derivative <b>30</b> exhibited inhibition of both MAO-A and -B (IC<sub>50</sub> =  ...[more]

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