| Identification | Back Directory | [Name]
2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol | [CAS]
524-69-6 | [Synonyms]
Xa
Nsc7359
Nsc 7359
Xylosyl a
Xylosyladenine
Xylo-adenosine
Adenine xyloside
9-(-D-Xylofuranosyl)adenine
9-(b-D-Xylofuranosyl)adenine
9-.beta.-D-Xylofuranosyladenine
Adenine, 9-.beta.-D-xylofuranosyl-
9H-Purin-6-amine, 9-β-D-xylofuranosyl-
9H-Purin-6-amine, 9-.beta.-D-xylofuranosyl-
9-(b-D-Xylofuranosyl)adenine,Xylo-adenosine, anticancer agent | [Molecular Formula]
C10H13N5O4 | [MDL Number]
MFCD30570252 | [MOL File]
524-69-6.mol | [Molecular Weight]
267.24 |
| Chemical Properties | Back Directory | [Melting point ]
125-140 °C | [Boiling point ]
676.3±65.0 °C(Predicted) | [density ]
2.08±0.1 g/cm3(Predicted) | [form ]
Solid | [pka]
13.11±0.70(Predicted) | [color ]
White to off-white | [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 |
| Hazard Information | Back Directory | [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.
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