Bridged 1,2,4-Trioxolanes: SnCl<sub>4</sub>—Catalyzed Synthesis and an In Vitro Study against <i>S. mansoni</i>
A synthesis of bridged 1,2,4-trioxolanes (bridged ozonides) from 1,5-diketones and hydrogen peroxide catalyzed by SnCl<sub>4</sub> was developed. It was shown that the ratio of target ozonides can be affected by the application of SnCl<sub>4</sub> as a catalyst and varying th...
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MDPI AG
2023-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/13/4913 |
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| author | Peter S. Radulov Ivan A. Yaremenko Jennifer Keiser Alexander O. Terent’ev |
| author_facet | Peter S. Radulov Ivan A. Yaremenko Jennifer Keiser Alexander O. Terent’ev |
| author_sort | Peter S. Radulov |
| collection | DOAJ |
| description | A synthesis of bridged 1,2,4-trioxolanes (bridged ozonides) from 1,5-diketones and hydrogen peroxide catalyzed by SnCl<sub>4</sub> was developed. It was shown that the ratio of target ozonides can be affected by the application of SnCl<sub>4</sub> 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<sub>4</sub>. The bridged ozonides were evaluated for their antischistosomal activity<b>.</b> These ozonides exhibited a very high activity against newly transformed schistosomula and adult <i>Schistosoma mansoni</i>. |
| first_indexed | 2024-03-11T01:34:37Z |
| format | Article |
| id | doaj.art-da346a32d34c46a8a04e1aad8d31e97c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T01:34:37Z |
| publishDate | 2023-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-da346a32d34c46a8a04e1aad8d31e97c2023-11-18T17:05:21ZengMDPI AGMolecules1420-30492023-06-012813491310.3390/molecules28134913Bridged 1,2,4-Trioxolanes: SnCl<sub>4</sub>—Catalyzed Synthesis and an In Vitro Study against <i>S. mansoni</i>Peter S. Radulov0Ivan A. Yaremenko1Jennifer Keiser2Alexander O. Terent’ev3N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, RussiaDepartment of Medical Parasitology and Infection Biology, Swiss Tropical and Public Health Institute, CH-4123 Allschwil, SwitzerlandN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, RussiaA synthesis of bridged 1,2,4-trioxolanes (bridged ozonides) from 1,5-diketones and hydrogen peroxide catalyzed by SnCl<sub>4</sub> was developed. It was shown that the ratio of target ozonides can be affected by the application of SnCl<sub>4</sub> 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<sub>4</sub>. The bridged ozonides were evaluated for their antischistosomal activity<b>.</b> These ozonides exhibited a very high activity against newly transformed schistosomula and adult <i>Schistosoma mansoni</i>.https://www.mdpi.com/1420-3049/28/13/4913peroxideozonidetin chloridehydrogen peroxideantischistosomal |
| spellingShingle | Peter S. Radulov Ivan A. Yaremenko Jennifer Keiser Alexander O. Terent’ev Bridged 1,2,4-Trioxolanes: SnCl<sub>4</sub>—Catalyzed Synthesis and an In Vitro Study against <i>S. mansoni</i> Molecules peroxide ozonide tin chloride hydrogen peroxide antischistosomal |
| title | Bridged 1,2,4-Trioxolanes: SnCl<sub>4</sub>—Catalyzed Synthesis and an In Vitro Study against <i>S. mansoni</i> |
| title_full | Bridged 1,2,4-Trioxolanes: SnCl<sub>4</sub>—Catalyzed Synthesis and an In Vitro Study against <i>S. mansoni</i> |
| title_fullStr | Bridged 1,2,4-Trioxolanes: SnCl<sub>4</sub>—Catalyzed Synthesis and an In Vitro Study against <i>S. mansoni</i> |
| title_full_unstemmed | Bridged 1,2,4-Trioxolanes: SnCl<sub>4</sub>—Catalyzed Synthesis and an In Vitro Study against <i>S. mansoni</i> |
| title_short | Bridged 1,2,4-Trioxolanes: SnCl<sub>4</sub>—Catalyzed Synthesis and an In Vitro Study against <i>S. mansoni</i> |
| title_sort | bridged 1 2 4 trioxolanes sncl sub 4 sub catalyzed synthesis and an in vitro study against i s mansoni i |
| topic | peroxide ozonide tin chloride hydrogen peroxide antischistosomal |
| url | https://www.mdpi.com/1420-3049/28/13/4913 |
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