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^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:63486
ChEMBL	ChEMBL374107^Y
ChemSpider	8325^Y
DrugBank	DB01667
ECHA InfoCard	100.004.681
EC Number	205-148-1
PubChem CID	135403646
RTECS number	XZ6157000
UNII	Q150359I72^Y
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)^Y Key: LPXQRXLUHJKZIE-UHFFFAOYSA-N^Y 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 C12=NNNC1=NC(=NC2=O)N
Properties
Chemical formula	C4H4N6O
Molar mass	152.117 g·mol^−1
Appearance	white to off-white crystalline powder[4]
Density	2.64 g/cm^3
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). Y verify (what is ^YN ?) 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]

References

1. "Azaguanine - Compound Summary (Descriptors)". National Center for Biotechnology Information. 27 March 2005. Retrieved 2009-03-03.
2. "8-azaguanine". Mondofacto. 12 December 1998. Archived from the original on 2010-02-15. Retrieved 2009-03-03.
3. "134-58-7, CAS Number: 3546-41-6". www.chemindustry.com. Archived from the original on 2011-07-16. Retrieved 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. 112 (1). University of California: Elsevier: 76. doi:10.1016/0003-9861(65)90012-3.
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". Butterworths. University of Michigan: 36.
8. "MSDS 7H-v-Triazolo(4,5-d)pyrimidin-7-one,5-amino-1,6-dihydro- CAS 134-58-7 MSDS * 8 AG * 5-Amino-1,6-dihydro-7H-v-triazolo(4,5-d)pyrimidin-7-one * 5-Amino-1,4-dihydro-7H-1,2,3-triazolo(4,5-d)pyrimidin-7-one * 5-Amino-7-hydroxy-1H-v-triazolo(d)pyrimidine * 5-Amino-1H-v-triazolo(d)pyrimidin-7-ol * Azaguanine * Azaguanine-8 * 8-Azaguanine * 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- * 7H-1,2,3-Triazolo(4,5-d)pyrimidin-7-one, 5-amino-1,4-dihydro-". www.chemcas.com. Retrieved 2009-03-03.
9. "Azaguanine - Compound Summary (Synonyms)". National Center for Biotechnology Information. 27 March 2005. Retrieved 2009-03-03.

External links

• Digital renderings of the molecule
• Some derivatives and similar molecules
• Web-based 3D viewer with the molecule
• "CAS: 134-58-7" on ChemCAS
• "Azaguanine^[permanent dead link‍]" on the Merck Index
• "Azaguanine" (CID 8646) on PubChem