Bridged 1,2,4-Trioxolanes: SnCl4—Catalyzed Synthesis and an In Vitro Study against S. mansoni

Bridged 1,2,4-Trioxolanes: SnCl4—Catalyzed Synthesis and an In Vitro Study against S. mansoni Full article

Journal

Molecules
ISSN: 1420-3049

Output data

Year: 2023, Volume: 28, Number: 13, Article number : 4913, Pages count : DOI: 10.3390/molecules28134913

Authors

Radulov Peter S. ¹ , Yaremenko Ivan A. ¹ , Keiser Jennifer ^2,3 , Terent’ev Alexander O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, Russia
2	Department of Medical Parasitology and Infection Biology, Swiss Tropical and Public Health Institute, CH-4123 Allschwil, Switzerland
3	University of Basel, CH-4003 Basel, Switzerland

A synthesis of bridged 1,2,4-trioxolanes (bridged ozonides) from 1,5-diketones and hydrogen peroxide catalyzed by SnCl4 was developed. It was shown that the ratio of target ozonides can be affected by the application of SnCl4 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 LiAlH4. The bridged ozonides were evaluated for their antischistosomal activity. These ozonides exhibited a very high activity against newly transformed schistosomula and adult Schistosoma mansoni.

Radulov P.S. , Yaremenko I.A. , Keiser J. , Terent’ev A.O.
Bridged 1,2,4-Trioxolanes: SnCl4—Catalyzed Synthesis and an In Vitro Study against S. mansoni
Molecules. 2023. V.28. N13. 4913 . DOI: 10.3390/molecules28134913 WOS Scopus OpenAlex

Web of science:	WOS:001028661200001
Scopus:	2-s2.0-85164844540
OpenAlex:	W4381804874

DB	Citing
OpenAlex	2
Scopus	3