関: ozonide

WordNet

any of a class of unstable chemical compounds resulting from the addition of ozone to a double bond in an unsaturated compound

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/05/13 02:29:42」(JST)

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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.^[1] 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.^[2]

References

^ Gary H. Posner, Michael H. Parker, John Northrop, Jeffrey S. Elias, Poonsakdi Ploypradith, Suji Xie,Theresa A. Shapiro (1999). "Orally Active, Hydrolytically Stable, Semisynthetic, Antimalarial Trioxanes in the Artemisinin Family". J. Med. Chem. 42 (2): 300–304. doi:10.1021/jm980529v. PMID 9925735.
^ Cumming, Jared N.; Ploypradith, Poonsakdi; Gary H. Posner (1997). "Antimalarial activity of artemisinin (qinghaosu) and related trioxanes: mechanism(s) of action". Advances in Pharmacology (San Diego) 37: 253–297.

English Journal

Determination of metabolic profile of anti-malarial trioxane CDRI 99/411 in rat liver microsomes using HPLC.

Mishra S, Manickavasagam L, Jain GK.SourcePharmacokinetics and Metabolism Division, Central Drug Research Institute (Council of Scientific and Industrial Research, India), Lucknow, Uttar Pradesh, India.
Biomedical chromatography : BMC.Biomed Chromatogr.2012 Jan;26(1):115-22. doi: 10.1002/bmc.1635. Epub 2011 Apr 19.
CDRI 99/411 is a potent 1,2,4-trioxane anti-malarial candidate compound of the Central Drug Research Institute, India. This study aimed to conduct comprehensive in vitro metabolic investigations of CDRI 99/411 to corroborate its preclinical investigations. Preliminary in vitro metabolic investigatio
PMID 21503937

The activity of dispiro peroxides against Fasciola hepatica.

Wang X, Zhao Q, Vargas M, Dong Y, Sriraghavan K, Keiser J, Vennerstrom JL.SourceCollege of Pharmacy, University of Nebraska Medical Center, 986025 Nebraska Medical Center, Omaha, NE, USA.
Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2011 Sep 15;21(18):5320-3. Epub 2011 Jul 19.
Dispiro 1,2,4-trioxanes and 1,2,4,5-tetraoxanes had superior efficacy against Fasciola hepatica than the corresponding ozonides (1,2,4-trioxolanes). For highest efficacy, spiroadamantane and carboxymethyl substructures were required. Three compounds completely cured F. hepatica-infected mice at sing
PMID 21802291

Japanese Journal

Synthesis of a Novel Artemisinin Analogue Having Potent Antimalarial Activity

Takasu Kiyosei,Katagiri Ruriko,Tanaka Yuko [他]
Heterocycles 54(2), 607-610, 2001-02
NAID 40005326995

Regiospecifically oxygen-18 labeled 1,2,4-trioxane : a simple chemical model system to probe the mechanism(s) for the antimalarial activity of artemisinin (qinghaosu)

POSNER G. H.
J Am Chem Soc 114(21), 8328-8329, 1992
NAID 80006728675

No electron-donating substituent effect on the singlet excited state formation from the 5-(5-aryl-2-pyrazinylamino)-1,2,4-trioxanes in dimethyl sulfoxide triggered by potassium t-butoxide.

Teranishi Katsunori,Goto Toshio
Bulletin of the Chemical Society of Japan 62(6), 2009-2012, 1989
… 5-(5-Phenyl-2-pyrazinylamino)-1,2,4-trioxane derivatives having a substituent on the 4 position of the phenyl group gave chemiluminescence in dimethyl sulfoxide by addition of potassium <I>t</I>-butoxide. …
NAID 130001980387

Related Pictures

File:1,2,4-Trioxane.png - Wikimedia names iupac name 1 2 4 trioxane Description 1,2,4-Trioxane-3D-balls.png peroxybis propane 2 2 13 kbyte 459 kbyte Trioxane — Wikipédia trioxane 1 2 4 trioxane is one of propane 2 2 13 kb 4 kb 459 kb 470 kb 9 kb

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リンク元

「ozonide」

1,2,4-Trioxane
Names
	IUPAC name 1,2,4-Trioxane
Identifiers
CAS Number	7049-17-4
ChemSpider	10629025
Jmol 3D model	Interactive image; Interactive image
	InChI InChI=1S/C3H6O3/c1-2-5-6-3-4-1/h1-3H2 Key: FQERLIOIVXPZKH-UHFFFAOYSA-N ; InChI=1/C3H6O3/c1-2-5-6-3-4-1/h1-3H2 Key: FQERLIOIVXPZKH-UHFFFAOYAX ;
	SMILES C1COCOO1 ; C1OCCOO1 ;
Properties
Chemical formula	C3H6O3
Molar mass	90.08 g·mol−1
Related compounds
Related compounds	1,3,5-trioxane; artemisinin
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references