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8-Azaguanine

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8-Azaguanine
Names
IUPAC names 5-amino-2,3-dihydrotriazolopyrimidin-7-one;
5-amino-1,4-dihydro-7H-1,2,3-triazolopyrimidin-7-one;
3-amino-2,4,7,8,9-pentazabicyclonona-1,3,6-trien-5-one
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.681 Edit this at Wikidata
EC Number
  • 205-148-1
PubChem CID
RTECS number
  • XZ6157000
UNII
CompTox Dashboard (EPA)
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)Key: LPXQRXLUHJKZIE-UHFFFAOYSA-N
  • 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
Appearance white to off-white crystalline powder
Density 2.64 g/cm
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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

8-Azaguanine is a purine analog with the chemical formula C4H4N6O. It has been widely studied for its biological activity. It shows antineoplastic activity and has been used in the treatment of acute leukemia.

Use in chemotherapy

The compound closely resembles guanine and appears to be competitive with it in the metabolism of living organisms. It has been shown to cause retardation of some malignant neoplasms when administered to tumors in animals. 8-Azaguanine was the first purine analogue discovered to inhibit experimental tumors in mice.

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:

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

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