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]
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| ECHA InfoCard | 100.004.681 |
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| 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.) |
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| 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).
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Use in chemotherapy
editThe 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
edit- 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-
References
edit- ^ "Azaguanine - Compound Summary (Descriptors)". National Center for Biotechnology Information. 27 March 2005. Retrieved 2009-03-03.
- ^ a b "8-azaguanine". Mondofacto. 12 December 1998. Archived from the original on 2010-02-15. Retrieved 2009-03-03.
- ^ a b "134-58-7, CAS Number: 3546-41-6". www.chemindustry.com. Archived from the original on 2011-07-16. Retrieved 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. 112 (1). University of California: Elsevier: 76. doi:10.1016/0003-9861(65)90012-3.
- ^ a b 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". Butterworths. University of Michigan: 36.
- ^ "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.
- ^ "Azaguanine - Compound Summary (Synonyms)". National Center for Biotechnology Information. 27 March 2005. Retrieved 2009-03-03.