2-Amino-6-chloro-2'-O-propargylpurine-9-riboside Chemical Properties

InChI

InChI=1/C13H14ClN5O5/c1-2-3-22-9-8(21)6(20)4-23-12(9)24-19-5-16-7-10(14)17-13(15)18-11(7)19/h1,5-6,8-9,12,20-21H,3-4H2,(H2,15,17,18)/t6-,8-,9-,12?/s3

InChIKey

QYKKSMWYIBCIBN-SFKBCKQCNA-N

SMILES

N1C2=C(N=C(N)N=C2Cl)N(OC2OC[C@@H](O)[C@@H](O)[C@H]2OCC#C)C=1 |&1:14,16,18,r|

2-Amino-6-chloro-2'-O-propargylpurine-9-riboside Usage And Synthesis

Description

2-Amino-6-chloro-2'-O-propargylpurine-9-riboside is a purine nucleoside analogue. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc. It is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

Uses

2-Amino-6-chloropurine-9-(2’-O-propargyl)riboside is a purine nucleoside analogue. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc[1]. 2-Amino-6-chloropurine-9-(2’-O-propargyl)riboside is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

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