313477-85-9

Usage

Uses

Used in Pharmaceutical Industry:
6-Chloro-2-Iodopurine-9-Riboside is used as a key intermediate in the synthesis of nucleoside analogues, which are widely utilized in the development of antiviral and anticancer drugs. Its presence of both chlorine and iodine atoms makes it a valuable substrate for further chemical modifications, enabling the creation of novel pharmaceutical agents with improved therapeutic properties.
Used in Antiviral Drug Development:
6-Chloro-2-Iodopurine-9-Riboside serves as a building block for the synthesis of nucleoside analogues that can inhibit viral replication. These analogues are designed to target specific viral enzymes or nucleic acid synthesis, thereby disrupting the viral life cycle and preventing the spread of infection.
Used in Anticancer Drug Development:
6-Chloro-2-Iodopurine-9-Riboside is employed in the development of nucleoside analogues that can interfere with the replication and transcription processes of cancer cells. These analogues can be incorporated into the DNA or RNA of cancer cells, leading to the inhibition of cell growth and the induction of cell death, thus offering potential therapeutic benefits in cancer treatment.
Used in Chemical Research:
6-Chloro-2-Iodopurine-9-Riboside is also utilized in chemical research for the exploration of novel chemical reactions and the synthesis of new compounds with potential applications in various fields, including medicine, materials science, and environmental science.

Upstream product

• 2004-07-1 2-Amino-6-chloropurine riboside 

Downstream Products

• 313477-86-0 2-iodo-N⁶-(2''-phenylethyl)adenosine 
• 124499-08-7 2-[[2''-(p-hydroxyphenyl)ethyl]amino]adenosine 
• 124498-53-9 (2R,3R,4S,5R)-2-[6-Amino-2-(2-hydroxy-2-phenyl-ethylamino)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol 

Relevant academic research and scientific papers

ADENOSINE ANALOGS FOR THE TREATMENT OF DISEASE

The disclosure provides adenosine analogs for the treatment of disease such as pain and inflammatory conditions.

Adenosine analogues as inhibitors of Trypanosoma brucei phosphoglycerate kinase: Elucidation of a novel binding mode for a 2-Amino-N6-substituted adenosine

As part of a project aimed at structure-based design of adenosine analogues as drugs against African trypanosomiasis, N6-, 2-amino-N6-, and N2-substituted adenosine analogues were synthesized and tested to establish structure - activity relationships for inhibiting Trypanosoma brucei glycosomal phosphoglycerate kinase (PGK), glyceraldehyde-3-phosphate dehydrogenase (GAPDH), and glycerol-3-phosphate dehydrogenase (GPDH). Evaluation of X-ray structures of parasite PGK, GAPDH, and GPDH complexed with their adenosyl-bearing substrates led us to generate a series of adenosine analogues which would target all three enzymes simultaneously. There was a modest preference by PGK for N6-substituted analogues bearing the 2-amino group. The best compound in this series, 2-amino-N6-[2-(p-hydroxyphenyl)ethyl]adenosine (46b), displayed a 23-fold improvement over adenosine with an IC50 of 130 μM. 2-[[2-(p-Hydroxyphenyl)ethyl]amino]adenosine (46c) was a weak inhibitor of T. brucei PGK with an IC50 of 500 μM. To explore the potential of an additive effect that having the N6 and N2 substitutions in one molecule might provide, the best ligands from the two series were incorporated into N6,N2-disubstituted adenosine analogues to yield N6-(2-phenylethyl)-2-[(2-phenylethyl)amino]adenosine (69) as a 30 μM inhibitor of T. brucei PGK which is 100-fold more potent than the adenosine template. In contrast, these series gave no compounds that inhibited parasitic GAPDH or GPDH more than 10-20% when tested at 1.0 mM. A 3.0 A? X-ray structure of a T. brucei PGK/46b complex revealed a binding mode in which the nucleoside analogue was flipped and the ribosyl moiety adopted a syn conformation as compared with the previously determined binding mode of ADP. Molecular docking experiments using QXP and SAS program suites reproduced this 'flipped and rotated' binding mode.