5-Aza-7-deazapurine

5-Aza-7-deazapurine or imidazo[1,2-a][1,3,5]triazine[1] is a heterocyclic aromatic organic compound that consists of a s-triazine ring fused to an imidazole ring. It is an isostere and isomer of purine. However, in 5-aza-7-deazapurine, N-9 of five-membered ring does not bonded with hydrogen. So 5-aza-7-deazapurine derivatives must have an exocyclic substituent with a double bond to bind a sugar residue.[2] 5-Aza-7-deazapurine nucleosides may have an oxo, thioxo, or a imine group.

5-Aza-7-deazapurine

Names
IUPAC name Imidazo[1,2-a][1,3,5]triazine
Other names 5-Aza-7-deazapurine
Identifiers
3D model (JSmol)	Interactive image
ChemSpider	14350821
PubChem CID	19734140
InChI InChI=1S/C5H4N4/c1-2-9-4-6-3-8-5(9)7-1/h1-4H^[pubchem] Key: OXISDMSERFAPRY-UHFFFAOYSA-N^[pubchem] InChI=1S/C5H4N4/c1-2-9-4-6-3-8-5(9)7-1/h1-4H Key: OXISDMSERFAPRY-UHFFFAOYSA-N
SMILES C1=CN2C=NC=NC2=N1
Properties
Chemical formula	C5H4N4
Molar mass	120.115 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Notable derivatives of this molecule include 5-aza-7-deazaguanine,[2] which is a nucleobase of hachimoji DNA.

See also

• Base analog
• Indolizine
• Purine analogue
• 7-Deazapurine
• Tubercidin

References

1. Seela, Frank; Amberg, Stefan; Melenewski, Alexander; Rosemeyer, Helmut (20 August 2001). "5-Aza-7-deazaguanine DNA: Recognition and Strand Orientation of Oligonucleotides Incorporating Anomeric Imidazo[1,2-a]-1,3,5-triazine Nucleosides". Helvetica. 84 (7): 1996–2014. doi:10.1002/1522-2675(20010711)84:7<1996::AID-HLCA1996>3.0.CO;2-1.
2. Chu, Chung K. Recent Advances in Nucleosides: Chemistry and Chemotherapy. Elsevier Science. p. 505. ISBN 9780444509512.