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Synthesis and NLRP3-Inflammasome Inhibitory Activity of the Naturally Occurring Velutone F and of Its Non-Natural Regioisomeric Chalconoids

Plant-derived remedies rich in chalcone-based compounds have been known for centuries in the treatment of specific diseases, and nowadays, the fascinating chalcone framework is considered a useful and, above all, abundant natural chemotype. Velutone F, a new chalconoid from Millettia velutina, exhib...

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Autores principales: De Ventura, Tiziano, Perrone, Mariasole, Missiroli, Sonia, Pinton, Paolo, Marchetti, Paolo, Strazzabosco, Giovanni, Turrin, Giulia, Illuminati, Davide, Cristofori, Virginia, Fantinati, Anna, Fabbri, Martina, Giorgi, Carlotta, Trapella, Claudio, Zanirato, Vinicio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9409317/
https://www.ncbi.nlm.nih.gov/pubmed/36012241
http://dx.doi.org/10.3390/ijms23168957
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author De Ventura, Tiziano
Perrone, Mariasole
Missiroli, Sonia
Pinton, Paolo
Marchetti, Paolo
Strazzabosco, Giovanni
Turrin, Giulia
Illuminati, Davide
Cristofori, Virginia
Fantinati, Anna
Fabbri, Martina
Giorgi, Carlotta
Trapella, Claudio
Zanirato, Vinicio
author_facet De Ventura, Tiziano
Perrone, Mariasole
Missiroli, Sonia
Pinton, Paolo
Marchetti, Paolo
Strazzabosco, Giovanni
Turrin, Giulia
Illuminati, Davide
Cristofori, Virginia
Fantinati, Anna
Fabbri, Martina
Giorgi, Carlotta
Trapella, Claudio
Zanirato, Vinicio
author_sort De Ventura, Tiziano
collection PubMed
description Plant-derived remedies rich in chalcone-based compounds have been known for centuries in the treatment of specific diseases, and nowadays, the fascinating chalcone framework is considered a useful and, above all, abundant natural chemotype. Velutone F, a new chalconoid from Millettia velutina, exhibits a potent effect as an NLRP3-inflammasome inhibitor; the search for new natural/non-natural lead compounds as NLRP3 inhibitors is a current topical subject in medicinal chemistry. The details of our work toward the synthesis of velutone F and the unknown non-natural regioisomers are herein reported. We used different synthetic strategies both for the construction of the distinctive benzofuran nucleus (BF) and for the key phenylpropenone system (PhP). Importantly, we have disclosed a facile entry to the velutone F via synthetic routes that can also be useful for preparing non-natural analogs, a prerequisite for extensive SAR studies on the new flavonoid class of NLRP3-inhibitors.
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spelling pubmed-94093172022-08-26 Synthesis and NLRP3-Inflammasome Inhibitory Activity of the Naturally Occurring Velutone F and of Its Non-Natural Regioisomeric Chalconoids De Ventura, Tiziano Perrone, Mariasole Missiroli, Sonia Pinton, Paolo Marchetti, Paolo Strazzabosco, Giovanni Turrin, Giulia Illuminati, Davide Cristofori, Virginia Fantinati, Anna Fabbri, Martina Giorgi, Carlotta Trapella, Claudio Zanirato, Vinicio Int J Mol Sci Article Plant-derived remedies rich in chalcone-based compounds have been known for centuries in the treatment of specific diseases, and nowadays, the fascinating chalcone framework is considered a useful and, above all, abundant natural chemotype. Velutone F, a new chalconoid from Millettia velutina, exhibits a potent effect as an NLRP3-inflammasome inhibitor; the search for new natural/non-natural lead compounds as NLRP3 inhibitors is a current topical subject in medicinal chemistry. The details of our work toward the synthesis of velutone F and the unknown non-natural regioisomers are herein reported. We used different synthetic strategies both for the construction of the distinctive benzofuran nucleus (BF) and for the key phenylpropenone system (PhP). Importantly, we have disclosed a facile entry to the velutone F via synthetic routes that can also be useful for preparing non-natural analogs, a prerequisite for extensive SAR studies on the new flavonoid class of NLRP3-inhibitors. MDPI 2022-08-11 /pmc/articles/PMC9409317/ /pubmed/36012241 http://dx.doi.org/10.3390/ijms23168957 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
De Ventura, Tiziano
Perrone, Mariasole
Missiroli, Sonia
Pinton, Paolo
Marchetti, Paolo
Strazzabosco, Giovanni
Turrin, Giulia
Illuminati, Davide
Cristofori, Virginia
Fantinati, Anna
Fabbri, Martina
Giorgi, Carlotta
Trapella, Claudio
Zanirato, Vinicio
Synthesis and NLRP3-Inflammasome Inhibitory Activity of the Naturally Occurring Velutone F and of Its Non-Natural Regioisomeric Chalconoids
title Synthesis and NLRP3-Inflammasome Inhibitory Activity of the Naturally Occurring Velutone F and of Its Non-Natural Regioisomeric Chalconoids
title_full Synthesis and NLRP3-Inflammasome Inhibitory Activity of the Naturally Occurring Velutone F and of Its Non-Natural Regioisomeric Chalconoids
title_fullStr Synthesis and NLRP3-Inflammasome Inhibitory Activity of the Naturally Occurring Velutone F and of Its Non-Natural Regioisomeric Chalconoids
title_full_unstemmed Synthesis and NLRP3-Inflammasome Inhibitory Activity of the Naturally Occurring Velutone F and of Its Non-Natural Regioisomeric Chalconoids
title_short Synthesis and NLRP3-Inflammasome Inhibitory Activity of the Naturally Occurring Velutone F and of Its Non-Natural Regioisomeric Chalconoids
title_sort synthesis and nlrp3-inflammasome inhibitory activity of the naturally occurring velutone f and of its non-natural regioisomeric chalconoids
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9409317/
https://www.ncbi.nlm.nih.gov/pubmed/36012241
http://dx.doi.org/10.3390/ijms23168957
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