8-Azaguanine

8-Azaguanine
Names
	IUPAC names 5-amino-2,3-dihydrotriazolo[4,5-d]pyrimidin-7-one;[1]; 5-amino-1,4-dihydro-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-one;[2]; 3-amino-2,4,7,8,9-pentazabicyclo[4.3.0]nona-1,3,6-trien-5-one[3]
Identifiers
CAS Number	134-58-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL374107 ;
ChemSpider	8325 ;
ECHA InfoCard	100.004.681
PubChem CID	8646;
RTECS number	XZ6157000;
UNII	Q150359I72 ;
CompTox Dashboard (EPA)	DTXSID0074508 ;
	InChI InChI=1S/C4H4N6O/c5-4-6-2-1(3(11)7-4)8-10-9-2/h(H4,5,6,7,8,9,10,11) Key: LPXQRXLUHJKZIE-UHFFFAOYSA-N ; InChI=1/C4H4N6O/c5-4-6-2-1(3(11)7-4)8-10-9-2/h(H4,5,6,7,8,9,10,11) Key: LPXQRXLUHJKZIE-UHFFFAOYAO;
	SMILES Nc2nc(=O)c1n[nH][nH]c1n2;
Properties
Chemical formula	C4H4N6O
Molar mass	152.117 g·mol−1
Appearance	white to off-white crystalline powder[4]
Density	2.64 g/cm³
Melting point	> 300 °C (decomp.)
Solubility in water	Insoluble
Hazards
Flash point	129.1 °C (264.4 °F; 402.2 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

8-Azaguanine is a purine analog with the chemical formula C₄H₄N₆O. It has been widely studied for its biological activity.[5] It shows antineoplastic activity and has been used in the treatment of acute leukemia.[2]

Use in chemotherapy

The compound closely resembles guanine and appears to be competitive with it in the metabolism of living organisms.[6] It has been shown to cause retardation of some malignant neoplasms when administered to tumors in animals.[6] 8-Azaguanine was the first purine analogue discovered to inhibit experimental tumors in mice.[7]

Synonyms

2-Amino-6-hydroxy-8-azapurine
2-Amino-6-oxy-8-azapurine
5-Amino-1,4-dihydro-7H-1,2,3-triazolo(4,5-d)pyrimidin-7-one
5-Amino-1,6-dihydro-7H-v-triazolo(4,5-d)pyrimidin-7-one
5-Amino-1H-triazolo(4,5-d)pyrimidin-7-ol
5-Amino-1H-v-triazolo(d)pyrimidin-7-ol
5-Amino-1H-(1,2,3)Triazolo(4,5-d)pyrimidin-7-ol
5-Amino-7-hydroxy-1H-v-triazolo(d)pyrimidine
7H-1,2,3-Triazolo(4,5-d)pyrimidin-7-one, 5-amino-1,4-dihydro- (9CI)
7H-1,2,3-Triazolo(4,5-d)pyrimidinone, 5-amino-1,4-dihydro-
7H-v-Triazolo(4,5-d)pyrimidin-7-one, 5-amino-1,6-dihydro-
8 AG
8azaG
Azaguanine

Azaguanine-8
Azan
AZG
B-28
Guanazol
Guanazolo
NSC-749
Pathocidin
Pathocidine
SF-337
SK 1150
Triazologuanine
v-Triazolo(4,5-d)pyrimidin-7-ol,5-amino-

* Sources:[3][8][9]

gollark: > It also criminalizes the act of circumventing an access control, whether or not there is actual infringement of copyright itself.according to the Wikipedia article.

gollark: And that being a problem is caused by DMCA section 1201.

gollark: They don't seem to be going after it because of piracy (except possibly due to the poor examples in the README) but because it could maybe be used to violate copyright, and that being illegal is a DMCA issue.

gollark: It isn't. Without it, there would basically not be a case against youtube-dl at all.

gollark: Again, it's the DMCA which makes the maybe-usable-to-violate-copyright things problematic in the first place.

References

"Azaguanine - Compound Summary (Descriptors)". National Center for Biotechnology Information. 27 March 2005. Retrieved 2009-03-03.
"8-azaguanine". Mondofacto. 12 December 1998. Retrieved 2009-03-03.
http://www.chemindustry.com/chemicals/747854.html Retrieved on 2009-03-03.
"8-AZAGUANINE". ChemicalLAND21.com. Retrieved 2009-03-03.
Tong, George L.; Lee, William W.; Goodman, Leon; Frederiksen, Sune (1965). "Synthesis of some 2′-deoxyribosides of 8-azaadenine". Archives of Biochemistry and Biophysics. University of California: Elsevier. 112 (1): 76. doi:10.1016/0003-9861(65)90012-3.
Colsky, J.; Meiselas, E.L.; Rosen, J.S.; Schulman, I. (1955). "Response of patients with leukemia to 8-azaguanine" (PDF). Blood. 10 (5): 482–92. doi:10.1182/blood.V10.5.482.482. PMID 14363328.
Timmis, G.M.; Williams, Donald Charles (1967). "Chemotherapy of Cancer: the Antimetabolite Approach: The Antimetabolite Approach". University of Michigan: Butterworths: 36. Cite journal requires |journal= (help)
http://www.chemcas.com/msds/cas/msds137/134-58-7.asp Retrieved on 2009-03-03.
"Azaguanine - Compound Summary (Synonyms)". National Center for Biotechnology Information. 27 March 2005. Retrieved 2009-03-03.

External links

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[1] "Azaguanine - Compound Summary (Descriptors)". National Center for Biotechnology Information. 27 March 2005. Retrieved 2009-03-03.

[mondo-2] "8-azaguanine". Mondofacto. 12 December 1998. Retrieved 2009-03-03.

[chemindustry-3] ttp://www.chemindustry.com/chemicals/747854.html Retrieved on 2009-03-03.

[4] "8-AZAGUANINE". ChemicalLAND21.com. Retrieved 2009-03-03.

[5] Tong, George L.; Lee, William W.; Goodman, Leon; Frederiksen, Sune (1965). "Synthesis of some 2′-deoxyribosides of 8-azaadenine". Archives of Biochemistry and Biophysics. University of California: Elsevier. 112 (1): 76. doi:10.1016/0003-9861(65)90012-3.

[response-6] Colsky, J.; Meiselas, E.L.; Rosen, J.S.; Schulman, I. (1955). "Response of patients with leukemia to 8-azaguanine" (PDF). Blood. 10 (5): 482–92. doi:10.1182/blood.V10.5.482.482. PMID 14363328.

[7] Timmis, G.M.; Williams, Donald Charles (1967). "Chemotherapy of Cancer: the Antimetabolite Approach: The Antimetabolite Approach". University of Michigan: Butterworths: 36. Cite journal requires |journal= (help)

[8] ttp://www.chemcas.com/msds/cas/msds137/134-58-7.asp Retrieved on 2009-03-03.

[9] "Azaguanine - Compound Summary (Synonyms)". National Center for Biotechnology Information. 27 March 2005. Retrieved 2009-03-03.