38048-32-7

Usage

Uses

Used in Pharmaceutical Research:
S-(4-Nitrobenzyl)-6-thioinosine is used as a prototype inhibitor for the human equilibrative nucleoside transporter (hENT1) with a high affinity ligand Kd of 0.1-1.0 nM. It is employed in the investigation of anticancer, antiviral, cardioprotective, and neuroprotective agents due to its role as a nucleoside transporter inhibitor.
Used in Anticancer Applications:
In the pharmaceutical industry, S-(4-Nitrobenzyl)-6-thioinosine is used as an inhibitor of hENT1 for studying the potential therapeutic applications in cancer treatment. Its ability to inhibit nucleoside transport can provide insights into the development of novel anticancer drugs.
Used in Antiviral Applications:
S-(4-Nitrobenzyl)-6-thioinosine is also used as a nucleoside transporter inhibitor in the development of antiviral drugs. By understanding its interaction with hENT1, researchers can explore new strategies to combat viral infections.
Used in Cardioprotective Applications:
In the field of cardiology, S-(4-Nitrobenzyl)-6-thioinosine serves as a research tool to investigate the role of nucleoside transport in heart protection and potential cardioprotective therapies.
Used in Neuroprotective Applications:
NBTI is utilized in neuroscience research to study the role of nucleoside transport in neuroprotection and the development of therapies for neurological disorders.
Used in Drug Delivery Systems:
S-(4-Nitrobenzyl)-6-thioinosine can be employed in the development of drug delivery systems, particularly for targeting the brain capillaries, due to its binding affinity to these sites. This application can be useful in enhancing the delivery and bioavailability of various therapeutic agents.

Biological Activity

Equilibrative nucleoside transporter 1 (ENT1) inhibitor (K i values are 0.4 and 2800 nM for hENT1 and hENT2 respectively).

Biochem/physiol Actions

Inhibitor of equilibrative nucleoside transporters (ENTs), particularly adenosine transporters, in central nervous system and vascular smooth muscle.

Upstream product

• 1356160-58-1 C₁₇H₂₀N₆O₇S*ClH 
• 100-14-1 4-nitrobenzyl chloride 
• 5987-73-5 2',3',5'-O-triacetyl-6-chloroinosine 
• 3510-73-4 (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate 
• 14215-97-5 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose 
• 87-42-3 6-chloropurine 
• 26798-33-4 (p-nitrophenyl)methanethiol 
• 2004-06-0 6-Chloropurine riboside 

Downstream Products

• 100-27-6 2-(4-nitrophenyl)ethanol 
• 91012-47-4 4-nitrobenzyl propyl sulfide 
• 574-25-4 6-mercaptopurine riboside 
• 92035-03-5 6-(propylthio)-9-(β-D-ribofuranosyl)purine 
• 143330-49-8 (2R,3R,4S,5R)-2-[6-(4-Hydroxyamino-benzylsulfanyl)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol 
• 143330-48-7 6-<<4-benzyl>thio>-9-(β-D-ribofuranosyl)purine 
• 99-99-0 1-methyl-4-nitrobenzene 
• 574-25-4 6-thioinosine 
• 130948-35-5 6-<(propylthio)thio>-9-(β-D-ribofuranosyl)purine 

Relevant academic research and scientific papers

Microwave-promoted "one-Pot" synthesis of 4- nitrobenzylthioinosine analogues using thiourea as a sulfur precursor

An efficient one-pot method for the synthesis of various C6-alkylthio-substituted purine nucleosides has been developed under microwave irradiation with good to excellent yields without any metal catalyst (see scheme). This process expands the scope of existing synthetic methodologies and was further successfully applied for synthesis of the biologically important compound 4-nitrobenzylthioinosine (NBTI).

Synthesis, Biological Activity and Molecular Modeling of 6-Benzylthioinosine Analogues as Subversive Substrates of Toxoplasma gondii Adenosine Kinase

Toxoplasma gondii is the most common cause of secondary CNS infections in immunocompromised persons such as AIDS patients. The major route of adenosine metabolism in T. gondii is direct phosphorylation to adenosine 5′-monophosphate (AMP) catalyzed by the enzyme adenosine kinase (EC 2.7.1.20). Adenosine kinase in T. gondii is significantly more active than any other purine salvage enzyme in this parasite and has been established as a potential chemotherapeutic target for the treatment of toxoplasmosis. Subversive substrates of T. gondii, but not the human, adenosine kinase are preferentially metabolized to their monophosphorylated forms and become selectively toxic to the parasites but not their host. 6-Benzylthioinosine (BTI) was identified as an excellent subversive substrate of T. gondii adenosine kinase. Herein, we report the synthesis of new analogues of BTI as subversive substrates for T. gondii adenosine kinase. These new subversive substrates were synthesized starting from tribenzoyl protected D-ribose. To accomplish the lead optimization process, a divergent and focused combinatorial library was synthesized using a polymer-supported trityl group at the 5′-position. The combinatorial library of 20 compounds gave several compounds more active than BTI. Structure-activity relationship studies showed that substitution at the para position plays a crucial role. To investigate the reasons for this discrimination, substrates with different substituents at the para position were studied by molecular modeling using Monte Carlo Conformational Search followed by energy minimization of the enzyme-ligand complex.