Bridged 1,2,4-Trioxolanes: SnCl(4)—Catalyzed Synthesis and an In Vitro Study against S. mansoni

A synthesis of bridged 1,2,4-trioxolanes (bridged ozonides) from 1,5-diketones and hydrogen peroxide catalyzed by SnCl(4) was developed. It was shown that the ratio of target ozonides can be affected by the application of SnCl(4) as a catalyst and varying the solvent. A wide range of bridged 1,2,4-t...

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Detalles Bibliográficos
Autores principales: Radulov, Peter S., Yaremenko, Ivan A., Keiser, Jennifer, Terent’ev, Alexander O.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10343456/
https://www.ncbi.nlm.nih.gov/pubmed/37446575
http://dx.doi.org/10.3390/molecules28134913
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author Radulov, Peter S.
Yaremenko, Ivan A.
Keiser, Jennifer
Terent’ev, Alexander O.
author_facet Radulov, Peter S.
Yaremenko, Ivan A.
Keiser, Jennifer
Terent’ev, Alexander O.
author_sort Radulov, Peter S.
collection PubMed
description A synthesis of bridged 1,2,4-trioxolanes (bridged ozonides) from 1,5-diketones and hydrogen peroxide catalyzed by SnCl(4) was developed. It was shown that the ratio of target ozonides can be affected by the application of SnCl(4) as a catalyst and varying the solvent. A wide range of bridged 1,2,4-trioxolanes (ozonides) was obtained in yields from 50 to 84%. The ozonide cycle was moderately resistant to the reduction of the ester group near the peroxide cycle to alcohol with LiAlH(4). The bridged ozonides were evaluated for their antischistosomal activity. These ozonides exhibited a very high activity against newly transformed schistosomula and adult Schistosoma mansoni.
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spelling pubmed-103434562023-07-14 Bridged 1,2,4-Trioxolanes: SnCl(4)—Catalyzed Synthesis and an In Vitro Study against S. mansoni Radulov, Peter S. Yaremenko, Ivan A. Keiser, Jennifer Terent’ev, Alexander O. Molecules Article A synthesis of bridged 1,2,4-trioxolanes (bridged ozonides) from 1,5-diketones and hydrogen peroxide catalyzed by SnCl(4) was developed. It was shown that the ratio of target ozonides can be affected by the application of SnCl(4) as a catalyst and varying the solvent. A wide range of bridged 1,2,4-trioxolanes (ozonides) was obtained in yields from 50 to 84%. The ozonide cycle was moderately resistant to the reduction of the ester group near the peroxide cycle to alcohol with LiAlH(4). The bridged ozonides were evaluated for their antischistosomal activity. These ozonides exhibited a very high activity against newly transformed schistosomula and adult Schistosoma mansoni. MDPI 2023-06-22 /pmc/articles/PMC10343456/ /pubmed/37446575 http://dx.doi.org/10.3390/molecules28134913 Text en © 2023 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
Radulov, Peter S.
Yaremenko, Ivan A.
Keiser, Jennifer
Terent’ev, Alexander O.
Bridged 1,2,4-Trioxolanes: SnCl(4)—Catalyzed Synthesis and an In Vitro Study against S. mansoni
title Bridged 1,2,4-Trioxolanes: SnCl(4)—Catalyzed Synthesis and an In Vitro Study against S. mansoni
title_full Bridged 1,2,4-Trioxolanes: SnCl(4)—Catalyzed Synthesis and an In Vitro Study against S. mansoni
title_fullStr Bridged 1,2,4-Trioxolanes: SnCl(4)—Catalyzed Synthesis and an In Vitro Study against S. mansoni
title_full_unstemmed Bridged 1,2,4-Trioxolanes: SnCl(4)—Catalyzed Synthesis and an In Vitro Study against S. mansoni
title_short Bridged 1,2,4-Trioxolanes: SnCl(4)—Catalyzed Synthesis and an In Vitro Study against S. mansoni
title_sort bridged 1,2,4-trioxolanes: sncl(4)—catalyzed synthesis and an in vitro study against s. mansoni
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10343456/
https://www.ncbi.nlm.nih.gov/pubmed/37446575
http://dx.doi.org/10.3390/molecules28134913
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