8-Azaguanine

8-Azaguanine
IUPAC name

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
PubChem 8646
ChemSpider 8325 Y
UNII Q150359I72 Y
ChEMBL CHEMBL374107 Y
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
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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]

Contents

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. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8646#Descriptors. Retrieved 2009-03-03. 
  2. ^ a b "8-azaguanine". Mondofacto. 12 December 1998. http://www.mondofacto.com/facts/dictionary?azaguanine. Retrieved 2009-03-03. 
  3. ^ a b http://www.chemindustry.com/chemicals/747854.html Retrieved on 2009-03-03.
  4. ^ "8-AZAGUANINE". ChemicalLAND21.com. http://chemicalland21.com/lifescience/phar/8-AZAGUANINE.htm. 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. http://bloodjournal.hematologylibrary.org/cgi/reprint/10/5/482.pdf 
  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. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8646&ncount=73#Synonyms. Retrieved 2009-03-03. 

External links