:8-Azaguanine
{{Chembox
| Watchedfields = changed
| verifiedrevid = 477226967
| ImageFile = 8-azaguanine.png
| ImageSize = 200px
| IUPACName = 5-amino-2,3-dihydrotriazolo[4,5-d]pyrimidin-7-one;{{cite web|title=Azaguanine - Compound Summary (Descriptors)|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8646#Descriptors|date=27 March 2005|publisher=National Center for Biotechnology Information|access-date=2009-03-03}}
5-amino-1,4-dihydro-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-one;{{cite web|url=http://www.mondofacto.com/facts/dictionary?azaguanine|date=12 December 1998|title=8-azaguanine|publisher=Mondofacto|access-date=2009-03-03|archive-date=2010-02-15|archive-url=https://web.archive.org/web/20100215051856/http://mondofacto.com/facts/dictionary?azaguanine|url-status=dead}}
3-amino-2,4,7,8,9-pentazabicyclo[4.3.0]nona-1,3,6-trien-5-one{{cite web |url=http://www.chemindustry.com/chemicals/747854.html |title=134-58-7, CAS Number: 3546-41-6 |website=www.chemindustry.com |access-date=2009-03-03 |archive-date=2011-07-16 |archive-url=https://web.archive.org/web/20110716070556/http://www.chemindustry.com/chemicals/747854.html |url-status=dead }}
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 134-58-7
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8325
| EC_number = 205-148-1
| ChEBI = 63486
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 374107
| DrugBank = DB01667
| PubChem = 135403646
| RTECS = XZ6157000
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Q150359I72
| 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)
| InChIKey = LPXQRXLUHJKZIE-UHFFFAOYAO
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H4N6O/c5-4-6-2-1(3(11)7-4)8-10-9-2/h(H4,5,6,7,8,9,10,11)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LPXQRXLUHJKZIE-UHFFFAOYSA-N
| SMILES = C12=NNNC1=NC(=NC2=O)N
}}
|Section2={{Chembox Properties
| C=4 | H=4 | N=6 | O=1
| Appearance = white to off-white crystalline powder{{cite web|url=http://chemicalland21.com/lifescience/phar/8-AZAGUANINE.htm|title=8-AZAGUANINE|publisher=ChemicalLAND21.com|access-date=2009-03-03}}
| Density = 2.64 g/cm3
| MeltingPt = > 300 °C (decomp.)
| BoilingPt =
| Solubility = Insoluble }}
|Section3={{Chembox Hazards
| NFPA-F = | NFPA-H = | NFPA-R =
| MainHazards =
| FlashPtC = 129.1
| AutoignitionPtC = }}
}}
8-Azaguanine is a purine analog with the chemical formula C4H4N6O. It has been widely studied for its biological activity.{{Cite journal|author=Tong, George L.|author2=Lee, William W.|author3= Goodman, Leon|author4= Frederiksen, Sune|title=Synthesis of some 2′-deoxyribosides of 8-azaadenine|year=1965|journal=Archives of Biochemistry and Biophysics|volume=112|issue=1|publisher=Elsevier|location=University of California|page=[https://books.google.com/books?id=mV0WAAAAIAAJ&q=azaguanine 76]|doi=10.1016/0003-9861(65)90012-3}} 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.{{Cite journal|author=Colsky, J.|author2=Meiselas, E.L.|author3= Rosen, J.S.|author4= Schulman, I.|year=1955|title=Response of patients with leukemia to 8-azaguanine|journal=Blood|volume=10|issue=5|pages=482–92|pmid=14363328|url=http://bloodjournal.hematologylibrary.org/cgi/reprint/10/5/482.pdf|doi=10.1182/blood.V10.5.482.482|doi-access=free}} 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.{{Cite journal|title=Chemotherapy of Cancer: the Antimetabolite Approach|last1=Timmis|first1=G.M.|last2=Williams|first2=Donald Charles|journal=Butterworths|year=1967|location=University of Michigan|page=36}}
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:{{cite web |url=http://www.chemcas.com/msds/cas/msds137/134-58-7.asp |title=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- |website=www.chemcas.com |access-date=2009-03-03}}{{cite web|title=Azaguanine - Compound Summary (Synonyms)|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8646&ncount=73#Synonyms|date=27 March 2005|publisher=National Center for Biotechnology Information|access-date=2009-03-03}}
References
External links
- [http://molecules.gnu-darwin.org/html/00550001_00575000/567032/ Digital renderings of the molecule]
- [http://molecules.gnu-darwin.org/mod/Azaguanine-more.html Some derivatives and similar molecules]
- [https://pubchem.ncbi.nlm.nih.gov/vw3d/vw3d.cgi?cmd=crtvw&reqid=399253100503692226&type=conf&totl=1 Web-based 3D viewer with the molecule]
- "[http://www.chemcas.com/material/cas/archive/134-58-7.asp CAS: 134-58-7]" on [http://www.chemcas.com/ ChemCAS]
- "[https://themerckindex.cambridgesoft.com/TheMerckIndex/TheMerckIndex/reversed/M0000896.txt Azaguanine]{{Dead link|date=September 2018 |bot=InternetArchiveBot |fix-attempted=yes }}" on the Merck Index
- "[https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8646 Azaguanine]" (CID 8646) on PubChem
{{DEFAULTSORT:Azaguanine, 8-}}