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]

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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.