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

[Image: see text] 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...

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Autores principales: Kamauchi, Hitoshi, Hirata, Momoka, Takao, Koichi, Sugita, Yoshiaki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9670909/
https://www.ncbi.nlm.nih.gov/pubmed/36406553
http://dx.doi.org/10.1021/acsomega.2c06260
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author Kamauchi, Hitoshi
Hirata, Momoka
Takao, Koichi
Sugita, Yoshiaki
author_facet Kamauchi, Hitoshi
Hirata, Momoka
Takao, Koichi
Sugita, Yoshiaki
author_sort Kamauchi, Hitoshi
collection PubMed
description [Image: see text] 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 (IC(50) = 17.8 and 15.8 μM, respectively).
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spelling pubmed-96709092022-11-18 Total Synthesis and Monoamine Oxidase Inhibitory Activities of (±)-Entonalactam A and Its Derivatives Kamauchi, Hitoshi Hirata, Momoka Takao, Koichi Sugita, Yoshiaki ACS Omega [Image: see text] 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 (IC(50) = 17.8 and 15.8 μM, respectively). American Chemical Society 2022-11-04 /pmc/articles/PMC9670909/ /pubmed/36406553 http://dx.doi.org/10.1021/acsomega.2c06260 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Kamauchi, Hitoshi
Hirata, Momoka
Takao, Koichi
Sugita, Yoshiaki
Total Synthesis and Monoamine Oxidase Inhibitory Activities of (±)-Entonalactam A and Its Derivatives
title Total Synthesis and Monoamine Oxidase Inhibitory Activities of (±)-Entonalactam A and Its Derivatives
title_full Total Synthesis and Monoamine Oxidase Inhibitory Activities of (±)-Entonalactam A and Its Derivatives
title_fullStr Total Synthesis and Monoamine Oxidase Inhibitory Activities of (±)-Entonalactam A and Its Derivatives
title_full_unstemmed Total Synthesis and Monoamine Oxidase Inhibitory Activities of (±)-Entonalactam A and Its Derivatives
title_short Total Synthesis and Monoamine Oxidase Inhibitory Activities of (±)-Entonalactam A and Its Derivatives
title_sort total synthesis and monoamine oxidase inhibitory activities of (±)-entonalactam a and its derivatives
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9670909/
https://www.ncbi.nlm.nih.gov/pubmed/36406553
http://dx.doi.org/10.1021/acsomega.2c06260
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