1,2,4-Trioxane

changed changed 477202901 1,2,4-Trioxane 1,2,4-Trioxane.png 1,2,4-Trioxane 1,2,4-Trioxane-3D-balls.png 140 Trioxane molecule 1,2,4-Trioxane C1COCOO1 correct chemspider 10629025 21584057 1/C3H6O3/c1-2-5-6-3-4-1/h1-3H2 C1OCCOO1 FQERLIOIVXPZKH-UHFFFAOYAX correct chemspider 1S/C3H6O3/c1-2-5-6-3-4-1/h1-3H2 correct chemspider FQERLIOIVXPZKH-UHFFFAOYSA-N Correct 7049-17-4 correct FDA X5CWB98J7S 3 6 3 1,3,5-trioxaneartemisinin 1,2,4-Trioxane is one of the isomers of trioxane. It has the molecular formula C3H6O3 and consists of a six membered ring with three carbon atoms and three oxygen atoms. The two adjacent oxygen atoms form a peroxide functional group and the other forms an ether functional group. It is like a cyclic acetal but with one of the oxygen atoms in the acetal group being replaced by a peroxide group. 1,2,4-Trioxane itself has not been isolated or characterized, but rather only studied computationally. However, it constitutes an important structural element of some more complex organic compounds. The natural compound artemisinin, isolated from the sweet wormwood plant (Artemisia annua), and some semi-synthetic derivatives are important antimalarial drugs containing the 1,2,4-trioxane ring. Completely synthetic analogs containing the 1,2,4-trioxane ring are important potential improvements over the naturally derived artemisinins. Gary H. Posner Gary H. Posner Michael H. Parker John Northrop Jeffrey S. Elias Poonsakdi Ploypradith Suji Xie Theresa A. Shapiro Orally Active, Hydrolytically Stable, Semisynthetic, Antimalarial Trioxanes in the Artemisinin Family J. Med. Chem. 1999 42 2 300–304 10.1021/jm980529v 9925735 The peroxide group in the 1,2,4-trioxane core of artemisinin is cleaved in the presence of the malaria parasite leading to reactive oxygen radicals that are damaging to the parasite.Cumming, Jared N. Ploypradith, Poonsakdi Gary H. Posner Gary H. Posner Antimalarial Activity of Artemisinin (Qinghaosu) and Related Trioxanes: Mechanism (S) of Action Advances in Pharmacology 1997 37 253–297 10.1016/s1054-3589(08)60952-7 8891104 9780120329380 References Category:Organic peroxides Category:Trioxanes Category:Hypothetical chemical compounds