6-Methoxy-9-(2-C-Methyl-beta-D-ribofuranosyl)purine Chemical Properties

Boiling point:

588.7±60.0 °C(Predicted)

Density 

1.70±0.1 g/cm3(Predicted)

pka

13.15±0.70(Predicted)

InChI

InChI=1S/C12H16N4O5/c1-12(19)8(18)6(3-17)21-11(12)16-5-15-7-9(16)13-4-14-10(7)20-2/h4-6,8,11,17-19H,3H2,1-2H3/t6-,8-,11-,12-/m1/s1

InChIKey

HFOYSXHOPVYGPB-YUTYNTIBSA-N

SMILES

OC[C@H]1O[C@@H](N2C3C(=C(N=CN=3)OC)N=C2)[C@](C)(O)[C@@H]1O

6-Methoxy-9-(2-C-Methyl-beta-D-ribofuranosyl)purine Usage And Synthesis

Description

6-Methoxy-9-(2-C-methyl-beta-D-ribofuranosyl)purine is a potent antiviral compound used in the research of viral infections, particularly those caused by herpes viruses. It exhibits a high selectivity index and low toxicity towards host cells, making it an effective option for suppressing viral replication. This nucleoside analogue inhibits the viral DNA polymerase, thus preventing viral DNA research and development and subsequent viral replication.

Uses

2′-C-Methyl-6-O-methylinosine is a hypoxanthine analog. Hypoxanthine is a kind of purine base mainly present in muscle tissue. And it is a metabolite produced by purine oxidase acting on xanthine. Hypoxanthine has typical anti-inflammatory effects and is a potential endogenous poly(ADP-ribose) polymerase (PARP) inhibitor. It is cytoprotective by inhibiting PAPR activity, inhibiting peroxynitrite-induced mitochondrial depolarization and secondary superoxide production. Hypoxanthine can also be used as an indicator of hypoxia[1][2].

References

[1] Virág L, Szabó C. Purines inhibit poly(ADP-ribose) polymerase activation and modulate oxidant-induced cell death. FASEB J. 2001 Jan;15(1):99-107. DOI:10.1096/fj.00-0299com
[2] Saugstad OD. Hypoxanthine as an indicator of hypoxia: its role in health and disease through free radical production. Pediatr Res. 1988 Feb;23(2):143-50. DOI:10.1203/00006450-198802000-00001