574-25-4

Usage

Uses

Used in Pharmaceutical Industry:
6-Mercaptopurine Riboside is used as a pharmaceutical compound for its role as a substrate for adenosine deaminase. It plays a crucial role in the development and functioning of certain medications, particularly those targeting adenosine deaminase deficiency and related conditions.
Used in Research and Development:
In the field of research and development, 6-Mercaptopurine Riboside is utilized as a key compound for studying the mechanisms of adenosine deaminase and its implications in various diseases. This helps in the advancement of medical knowledge and the development of novel therapeutic strategies.
Used in Biochemical Analysis:
6-Mercaptopurine Riboside is also employed in biochemical analysis as a reference compound for the assessment of adenosine deaminase activity. This aids in understanding the enzyme's role in biological processes and its potential as a therapeutic target.

Purification Methods

Recrystallise the riboside from H2O or EtOH. It has UV max in H2O at 322nm (pH 1), 320 nm (pH 6.7) and 310nm (pH 13). [IR: Johnson et al. J Am Chem Soc 80 699 1958, UV: Fox et al. J Am Chem Soc 80 1669 1958, Beilstein 26 III/IV 2100.]

InChI:InChI=1/C10H12N4O4S/c15-1-4-6(16)7(17)10(18-4)14-3-13-5-8(14)11-2-12-9(5)19/h2-4,6-7,10,15-17H,1H2,(H,11,12,19)/p-1/t4-,6-,7-,10-/m1/s1

Upstream product

• 2004-06-0 6-Chloropurine riboside 
• 17356-08-0 thiourea 
• 6741-90-8 2',3',5'-tri-O-benzoyl-6-thioinosine 
• 38048-32-7 nitrobenzylthioinosine 
• 107-03-9 1-thiopropane 
• 130948-35-5 6-<(propylthio)thio>-9-(β-D-ribofuranosyl)purine 
• 6741-88-4 2',3',5'-tri-O-benzoylinosine 
• 58-63-9 Inosine 
• 6741-88-4 O^2'_,O3'_,O5'-tribenzoyl-inosine 
• 19399-25-8 N⁶-methoxyadenosine 
• 67-56-1 methanol 
• 157930-09-1 6-Mercaptopurine 
• 58-96-8 uridine 
• 108321-99-9 α,β-D-ribofuranose-5-phophate disodium salt 

Downstream Products

• 51375-22-5 6-phenacylthioinosine 
• 71052-74-9 6-acetonylthioinosine 
• 600736-36-5 6-(2,4-dinitrophenyl)thioinosine 
• 6165-03-3 6-benzylthio-purine riboside 
• 1359697-42-9 2',3'-O-isopropylidene-5'-O-(di-tert-butylphosphoramidite)-6-(2,4-dinitrophenyl)thioinosine 
• 53-83-8 6-thioinosine 5'-monophosphate 
• 60095-36-5 2',3'-O-isopropylidene-6-thioinosine 
• 342-69-8 6-methylmercaptopurine riboside 
• 51375-21-4 (2R,3R,4S,5R)-2-[6-(4-Chloro-benzylsulfanyl)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol 
• 550-33-4 Nebularin 
• 3021-21-4 6-thio-9-(2',3',5'-tri-O-acetyl-β-D-ribosyl)purine 

Relevant academic research and scientific papers

Chemoselective Perfluoromethylation of Thio- And Selenoamides

A chemo- and regioselective perfluoromethylation using thioamides/selenoamides (prepared one step from corresponding lactams) as starting materials has been discovered. The reaction demonstrated complementary chemoselectivity to the C-H trifluoromethylation of (hetero)arenes as well as remarkable functional group compatibility especially toward radical sensitive olefin-, alkyne-, and arylhalide-bearing substrates. The examples of perfluorothio-/selenolated drug molecules indicated application potential of this strategy in drug modification and drug-analogue preparation.

Heterocyclic compound containing SCF3 or SeCF3, and preparation method thereof

The invention discloses a heterocyclic compound containing SCF3 or SeCF3, and a preparation method thereof. The preparation method comprises: dissolving a chlorinated heterocyclic compound 1 in an EtOH solution, adding 1.0-2.0 equivalent weight of thiourea or selenourea, then stirring for 1-8 hours at 50-120 DEG C, and reacting to obtain a compound 2; and dissolving the compound 2 in an Acetone orEA solution, adding 2.0-4.0 equivalent weight of CF3SO2Na and 0.2-0.4 equivalent weight of a Cu salt, adding 2.0-4.0 equivalent weight of a tBuOOH solution in a dropwise manner, and reacting at 25-40DEG C for 1.0-2.0 hours to obtain a compound 3, namely the required SCF3 or SeCF3-containing heterocyclic compound. According to the invention, the synthesized compound has huge potential in the aspect of treating diseases; and according to the synthetic route provided by the invention, amplification can be realized in each step, the yield can reach 85%, the synthetic route provided by the invention brings a simpler and more effective way for synthesis of compounds with biological activity, the yield is high, large-scale preparation can be realized, and the synthetic route has a very wide application prospect.

Thio- or seleno-amide compound and preparation method thereof

The invention discloses a thio- or seleno-amide compound and a preparation method thereof. The preparation method comprises the following steps of dissolving a chlorinated aromatic heterocyclic compound 1 in an EtOH solution, adding 1.0-2.0 times of equivalent thiourea or selenourea, stirring at 50-120 DEG C for 1-8 hours, and reacting to obtain a compound 2, namely the required thio- or seleno-amide compound. Each step of the synthetic route can be amplified, the yield can reach 85 percent, the synthesized compound provides a medical intermediate for synthesizing purine derivatives containingSCF3 or SeCF3, the synthetic route provided by the invention brings a simpler and more effective way for synthesizing compounds with biological activity, the yield is high, large-scale preparation can be realized, and the application prospect is very wide.

Structure-Guided Tuning of a Selectivity Switch towards Ribonucleosides in Trypanosoma brucei Purine Nucleoside 2′-Deoxyribosyltransferase

The use of nucleoside 2′-deoxyribosyltransferases (NDTs) as biocatalysts for the industrial synthesis of nucleoside analogues is often hindered by their strict preference for 2′-deoxyribonucleosides. It is shown herein that a highly versatile purine NDT from Trypanosoma brucei (TbPDT) can also accept ribonucleosides as substrates; this is most likely because of the distinct role played by Asn53 at a position that is usually occupied by Asp in other NDTs. Moreover, this unusual activity was improved about threefold by introducing a single amino acid replacement at position 5, following a structure-guided approach. Biophysical and biochemical characterization revealed that the TbPDTY5F variant is a homodimer that displays maximum activity at 50 °C and pH 6.5 and shows a remarkably high melting temperature of 69 °C. Substrate specificity studies demonstrate that 6-oxopurine ribonucleosides are the best donors (inosine>guanosine?adenosine), whereas no significant preferences exist between 6-aminopurines and 6-oxopurines as base acceptors. In contrast, no transferase activity could be detected on xanthine and 7-deazapurines. TbPDTY5F was successfully employed in the synthesis of a wide range of modified ribonucleosides containing different purine analogues.

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.

Simple method for fast deprotection of nucleosides by triethylamine- catalyzed methanolysis of acetates in aqueous medium

A straightforward methodology for deacetylation of protected ribonucleosides was developed based on triethylamine-catalyzed solvolysis in aqueous methanol. Reactions are completed in a few minutes under microwave irradiation and the free nucleosides are obtained in high yield after simple evaporation of volatiles. Other important features include the involvement of readily available reagents and the compatibility with diverse functional groups, which make this process very attractive for broad application.

Reaction mechanisms of allicin and allyl-mixed disulfides with proteins and small thiol molecules

Allylsulfides from garlic are chemopreventive agents. Entering cells they are expected to initially interact with glutathione. Accordingly, reaction mechanisms of the product, S-allylthio-glutathione, with model proteins and thiols were analyzed in cell f

Aeromonas hydrophila strains as biocatalysts for transglycosylation

Microbial transglycosylation is useful as a green alternative in the preparation of purine nucleosides and analogues, especially for those that display pharmacological activities. In a search for new transglycosylation biocatalysts, two Aeromonas hydrophila strains were selected. The substrate specificity of both micro-organisms was studied and, as a result, several nucleoside analogues have been prepared. Among them, ribavirin, a broad spectrum antiviral, and the well-known anti HIV didanosine, were prepared, in 77 and 62% yield using A. hydrophila CECT 4226 and A. hydrophila CECT 4221, respectively. In order to scale-up the processes, the reaction conditions, product purification and biocatalyst preparation were analyzed and optimized.

Chemoenzymatic preparation of nucleosides from furanoses

Chemoenzymatic preparation of ribose, deoxyribose and arabinose 5-phosphates was accomplished. These compounds were tested as starting materials in the enzymatic preparation of natural and modified purine and pyrimidine nucleosides, using an overexpressed Escherichia coli phosphopentomutase.

Purine nucleoside synthesis from uridine using immobilised Enterobacter gergoviae CECT 875 whole cells

Biocatalysed purine nucleoside synthesis was carried out using immobilised Enterobacter gergoviae CECT 875. Similar yields (80-95%) in adenosine were obtained with both free and immobilised cells though in the last case a long reaction time was necessary. The immobilised cells can be reused at least for more than 30 times without significant loss of enzymatic activity. The immobilised biocatalyst in agarose is active in the synthesis of unnatural nucleosides.