8-Azaguanine

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8-Azaguanine
8-azaguanine.png
Identifiers
CAS number 134-58-7 YesY
PubChem 8646
ChemSpider 8325 YesY
UNII Q150359I72 YesY
ChEMBL CHEMBL374107 YesY
RTECS number XZ6157000
Jmol-3D images Image 1
Properties
Molecular formula C4H4N6O
Molar mass 152.11 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 noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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[edit]

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[edit]

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

References[edit]

  1. ^ "Azaguanine - Compound Summary (Descriptors)". National Center for Biotechnology Information. 27 March 2005. Retrieved 2009-03-03. 
  2. ^ a b "8-azaguanine". Mondofacto. 12 December 1998. Retrieved 2009-03-03. 
  3. ^ a b http://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. 
  6. ^ a b Colsky, J.; Meiselas, E.L.; Rosen, J.S.; Schulman, I. (1955). "Response of patients with leukemia to 8-azaguanine". Blood 10 (5): 482–92. PMID 14363328. 
  7. ^ Timmis, G.M.; Williams, Donald Charles (1967). "Chemotherapy of Cancer: the Antimetabolite Approach: The Antimetabolite Approach". University of Michigan: Butterworths. p. 36. 
  8. ^ http://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. 

External links[edit]