9-(β-D-Xylofuranosyl)adenine Chemical Properties

Melting point:

125-140 °C

Boiling point:

676.3±65.0 °C(Predicted)

Density 

2.08±0.1 g/cm3(Predicted)

pka

13.11±0.70(Predicted)

InChI

InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)

InChIKey

OIRDTQYFTABQOQ-UHFFFAOYSA-N

SMILES

O1C(CO)C(O)C(O)C1N1C2=C(N=C1)C(N)=NC=N2

9-(β-D-Xylofuranosyl)adenine Usage And Synthesis

Uses

9-(β-d-Xylofuranosyl)adenine (xylo-A) was synthesized long ago and found to be effective in prolonging the survival time of mice bearing TA3 or Ehrlich ascites tumours. It is an adenosine analog. Adenosine analogs mostly act as smooth muscle vasodilators and have also been shown to inhibit cancer progression. 9-(β-d-Arabinofuranosyl)adenine (vidarabine), which was reported to have similar antitumour properties to xylo-A, is now being used clinically as an antiviral agent[1].

Definition

ChEBI: A purine nucleoside in which adenine is attached to xylofuranose via a beta-N9-glycosidic bond.

References

[1] Yutaka Kubota. “Synthesis and antiviral evaluation of 4’-alkoxy analogues of 9-(beta-D-xylofuranosyl)adenine.” Antiviral Chemistry and Chemotherapy 19 5 (2009): 201–12.