Antimalarial troponoids, puberulic acid and viticolins; divergent synthesis and structure-activity relationship studies

Abstract Divergent synthesis of antimalarial troponoids, including naturally occurring compounds, some of which were identified and isolated by our group, has been achieved utilizing the total synthetic route of puberulic acid. Structure-activity relationships of natural products and simple troponoi...

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Autores principales:	Goh Sennari, Ryo Saito, Tomoyasu Hirose, Masato Iwatsuki, Aki Ishiyama, Rei Hokari, Kazuhiko Otoguro, Satoshi Ōmura, Toshiaki Sunazuka
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/6625936338a845379b8e4d5e81716ef2
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spelling	oai:doaj.org-article:6625936338a845379b8e4d5e81716ef22021-12-02T11:52:44ZAntimalarial troponoids, puberulic acid and viticolins; divergent synthesis and structure-activity relationship studies10.1038/s41598-017-07718-32045-2322https://doaj.org/article/6625936338a845379b8e4d5e81716ef22017-08-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-07718-3https://doaj.org/toc/2045-2322Abstract Divergent synthesis of antimalarial troponoids, including naturally occurring compounds, some of which were identified and isolated by our group, has been achieved utilizing the total synthetic route of puberulic acid. Structure-activity relationships of natural products and simple troponoids inspired us to explore more detailed properties of this class of compounds. Access to new derivatives was facilitated through intermediate compounds generated during the total synthesis of puberulic acid by a stepwise oxidation-aromatization sequence to provide 7-hydroxytropolones and bromination for conversion of the carboxylic acid moiety. The first total synthesis of viticolin A, as well as the synthesis of different methyl-substituted derivatives, has also been achieved. In vitro antimalarial activity and cytotoxicity of novel derivatives were evaluated and fundamental information to facilitate the discovery of more promising antimalarials was obtained.Goh SennariRyo SaitoTomoyasu HiroseMasato IwatsukiAki IshiyamaRei HokariKazuhiko OtoguroSatoshi ŌmuraToshiaki SunazukaNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-9 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Goh Sennari Ryo Saito Tomoyasu Hirose Masato Iwatsuki Aki Ishiyama Rei Hokari Kazuhiko Otoguro Satoshi Ōmura Toshiaki Sunazuka Antimalarial troponoids, puberulic acid and viticolins; divergent synthesis and structure-activity relationship studies
description	Abstract Divergent synthesis of antimalarial troponoids, including naturally occurring compounds, some of which were identified and isolated by our group, has been achieved utilizing the total synthetic route of puberulic acid. Structure-activity relationships of natural products and simple troponoids inspired us to explore more detailed properties of this class of compounds. Access to new derivatives was facilitated through intermediate compounds generated during the total synthesis of puberulic acid by a stepwise oxidation-aromatization sequence to provide 7-hydroxytropolones and bromination for conversion of the carboxylic acid moiety. The first total synthesis of viticolin A, as well as the synthesis of different methyl-substituted derivatives, has also been achieved. In vitro antimalarial activity and cytotoxicity of novel derivatives were evaluated and fundamental information to facilitate the discovery of more promising antimalarials was obtained.
format	article
author	Goh Sennari Ryo Saito Tomoyasu Hirose Masato Iwatsuki Aki Ishiyama Rei Hokari Kazuhiko Otoguro Satoshi Ōmura Toshiaki Sunazuka
author_facet	Goh Sennari Ryo Saito Tomoyasu Hirose Masato Iwatsuki Aki Ishiyama Rei Hokari Kazuhiko Otoguro Satoshi Ōmura Toshiaki Sunazuka
author_sort	Goh Sennari
title	Antimalarial troponoids, puberulic acid and viticolins; divergent synthesis and structure-activity relationship studies
title_short	Antimalarial troponoids, puberulic acid and viticolins; divergent synthesis and structure-activity relationship studies
title_full	Antimalarial troponoids, puberulic acid and viticolins; divergent synthesis and structure-activity relationship studies
title_fullStr	Antimalarial troponoids, puberulic acid and viticolins; divergent synthesis and structure-activity relationship studies
title_full_unstemmed	Antimalarial troponoids, puberulic acid and viticolins; divergent synthesis and structure-activity relationship studies
title_sort	antimalarial troponoids, puberulic acid and viticolins; divergent synthesis and structure-activity relationship studies
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/6625936338a845379b8e4d5e81716ef2
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Antimalarial troponoids, puberulic acid and viticolins; divergent synthesis and structure-activity relationship studies

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