6165-03-3

Usage

Molecular structure

The compound contains a purine base, a benzylsulfanyl group, and an oxolane ring with hydroxymethyl substituents.

Classification

It is a nucleoside analog.

Potential properties

The compound has potential antiviral and anti-neoplastic properties.

Possible mechanism of action

It may work by interfering with nucleic acid synthesis and inhibiting the growth of cancer cells.

Additional properties

It may also have immunosuppressive properties.

Current status

It has been studied for its potential in treating viral infections and cancer.

Future research

Further research is needed to fully understand the potential applications and mechanisms of action of 2-(6-benzylsulfanylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol.

InChI:InChI=1/C17H18N4O4S/c22-6-11-13(23)14(24)17(25-11)21-9-20-12-15(21)18-8-19-16(12)26-7-10-4-2-1-3-5-10/h1-5,8-9,11,13-14,17,22-24H,6-7H2

Upstream product

• 3492-64-6 sodium benzylmercaptide 
• 2004-06-0 6-Chloropurine riboside 
• 64-17-5 ethanol 
• 574-25-4 6-thioinosine 
• 19399-25-8 N⁶-methoxyadenosine 
• 58-63-9 Inosine 
• 100-44-7 benzyl chloride 
• 574-25-4 6-mercaptopurine riboside 
• 1356160-58-1 C₁₇H₂₀N₆O₇S*ClH 
• 5987-73-5 2',3',5'-O-triacetyl-6-chloroinosine 
• 100-53-8 phenylmethanethiol 
• 385806-21-3 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-(imidazol-1-yl)purine 
• 3181-38-2 2',3',5'-tri-O-acetylinosine 
• 309253-78-9 6-(1H-imidazol-1-yl)-9-(β-D-ribofuranosyl)purine 

Relevant academic research and scientific papers

α,β-Methylene-ADP (AOPCP) Derivatives and Analogues: Development of Potent and Selective ecto-5′-Nucleotidase (CD73) Inhibitors

ecto-5′-Nucleotidase (eN, CD73) catalyzes the hydrolysis of extracellular AMP to adenosine. eN inhibitors have potential for use as cancer therapeutics. The eN inhibitor α,β-methylene-ADP (AOPCP, adenosine-5′-O-[(phosphonomethyl)phosphonic acid]) was used as a lead structure, and derivatives modified in various positions were prepared. Products were tested at rat recombinant eN. 6-(Ar)alkylamino substitution led to the largest improvement in potency. N6-Monosubstitution was superior to symmetrical N6,N6-disubstitution. The most potent inhibitors were N6-(4-chlorobenzyl)- (10l, PSB-12441, Ki 7.23 nM), N6-phenylethyl- (10h, PSB-12425, Ki 8.04 nM), and N6-benzyl-adenosine-5′-O-[(phosphonomethyl)phosphonic acid] (10g, PSB-12379, Ki 9.03 nM). Replacement of the 6-NH group in 10g by O (10q, PSB-12431) or S (10r, PSB-12553) yielded equally potent inhibitors (10q, 9.20 nM; 10r, 9.50 nM). Selected compounds investigated at the human enzyme did not show species differences; they displayed high selectivity versus other ecto-nucleotidases and ADP-activated P2Y receptors. Moreover, high metabolic stability was observed. These compounds represent the most potent eN inhibitors described to date.

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).

Testing nucleoside analogues as inhibitors of Bacillus anthracis spore germination in vitro and in macrophage cell culture

Bacillus anthracis, the etiological agent of anthrax, has a dormant stage in its life cycle known as the endospore. When conditions become favorable, spores germinate and transform into vegetative bacteria. In inhalational anthrax, the most fatal manifest

Mild and efficient functionalization at C6 of purine 2′-deoxynucleosides and ribonucleosides

(Equation Presented) Treatment of sugar-protected inosine and 2′-deoxyinosine derivatives with a cyclic secondary amine or imidazole and I2/Ph3P/EtN(i-Pr)2/(CH2-Cl 2 or toluene) gave quantitative conversions into 6-N-(substituted)purine nucleosides. SNAr reactions with (imidazol-1-yl) derivatives gave 6-(N, O, or S)-substituted products. The 6-(benzylsulfonyl) group underwent SNAr displacement with an arylamine at ambient temperature.

Photochemistry of Nucleoside Transport Inhibitor 6-S-Benzylated Thiopurine Ribonucleosides. Implications for a New Class of Photoaffinity Labels

Photochemistry of the nucleoside transport inhibitor 6--9-(β-D-ribofuranosyl)purine (NBMPR, 1) yielded products from the initial homolytic cleavage of the benzyl-sulfur bond.Photoreduction of the nitro group also occurred to a minor e

6-Substituted purine 3',5'-cyclic nucleotides

Described herein are novel 6-alkylthio and 6-arylalkylthio purine 3',5' cyclic nucleotides variously exhibiting adenyl cyclase and (in animal studies) tumor inhibitory properties, interferon potentiation, antiviral activity, and the ability to activate adenosine 3',5'-cyclic phosphate-dependent protein kinase while enjoying resistance to phosphodiesterase hydrolysis superior to that of its naturally occuring analog. The compounds are obtained by alkylation of the corresponding 6-thio nucleotide, which is in turn provided by a novel synthetic route