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27462-39-1

27462-39-1 Structure

27462-39-1 Structure
IdentificationBack Directory
[Name]

2-Amino-9-(β-D-xylofuranosyl)-1,9-dihydro-6H-purin-6-one
[CAS]

27462-39-1
[Synonyms]

Nsc115607
Xylo-guanosine
9-(-D-Xylofuranosyl)guanine
9-(b-D-Xylofuranosyl)guanine
9-(.beta.-D-Xylofuranosyl)guanine
Guanine, 9-.beta.-D-xylofuranosyl-
9-(b-D-Xylofuranosyl)guanine,Xylo-guanosine
2-Amino-9-(β-D-xylofuranosyl)-1,9-dihydro-6H-purin-6-one
6H-Purin-6-one, 2-amino-1,9-dihydro-9-β-D-xylofuranosyl-
Wln: T56 bn dn fvm inj hz B1- bt5otj cq dq eq -D,beta,xylo
6H-Purin-6-one, 2-amino-1,7-dihydro-9-.beta.-D-xylofuranosyl-
[Molecular Formula]

C10H13N5O5
[MDL Number]

MFCD01723953
[MOL File]

27462-39-1.mol
[Molecular Weight]

283.24
Chemical PropertiesBack Directory
[InChI]

InChI=1/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5+,6-,9-/s3
[InChIKey]

NYHBQMYGNKIUIF-SQEVNGKDNA-N
[SMILES]

C12N=C(NC(=O)C=1N=CN2[C@H]1[C@H](O)[C@@H](O)[C@@H](CO)O1)N |&1:10,11,13,15,r|
Hazard InformationBack Directory
[Uses]

9-(β-D-Xylofuranosyl)guanine is a guanosine analog. Some guanosine analogs have immunostimulatory activity. In some animal models, they also induce type I interferons, producing antiviral effects. Studies have shown that the functional activity of guanosine analogs is dependent on the activation of Toll-like receptor 7 (TLR7)[1].
[References]

[1] Robak T, Robak P. Purine nucleoside analogs in the treatment of rarer chronic lymphoid leukemias. Curr Pharm Des. 2012;18(23):3373-88. DOI:10.2174/138161212801227005
[2] Lee J, et al. Molecular basis for the immunostimulatory activity of guanine nucleoside analogs: activation of Toll-like receptor 7. Proc Natl Acad Sci U S A. 2003 May 27;100(11):6646-51. DOI:10.1073/pnas.0631696100
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