Chemistry:8-Azaguanine

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8-Azaguanine
8-azaguanine.png
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
EC Number
  • 205-148-1
RTECS number
  • XZ6157000
UNII
Properties
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.)
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).
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Infobox references
Tracking categories (test):

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. https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8646#Descriptors. 
  2. ↑ 2.0 2.1 "8-azaguanine". Mondofacto. 12 December 1998. http://www.mondofacto.com/facts/dictionary?azaguanine. 
  3. ↑ 3.0 3.1 "134-58-7, CAS Number: 3546-41-6". http://www.chemindustry.com/chemicals/747854.html. 
  4. ↑ "8-AZAGUANINE". ChemicalLAND21.com. http://chemicalland21.com/lifescience/phar/8-AZAGUANINE.htm. 
  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. ↑ 6.0 6.1 Colsky, J.; Meiselas, E.L.; Rosen, J.S.; Schulman, I. (1955). "Response of patients with leukemia to 8-azaguanine". Blood 10 (5): 482–92. doi:10.1182/blood.V10.5.482.482. 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". 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-". http://www.chemcas.com/msds/cas/msds137/134-58-7.asp. 
  9. ↑ "Azaguanine - Compound Summary (Synonyms)". National Center for Biotechnology Information. 27 March 2005. https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8646&ncount=73#Synonyms. 

External links



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