6305-94-8

Basic information

• Product Name: 1,7,8,9-tetrahydro-8-thioxo-6H-purin-6-one
• Synonyms: 1,7,8,9-tetrahydro-8-thioxo-6H-purin-6-one;6-HYDROXY-8-MERCAPTOPURINE (6OH8SP);6H-Purin-6-one, 1,7,8,9-tetrahydro-8-thioxo-;6-Hydroxy-8-mercaptopurine;8-Mercaptohypoxanthine;8-Thiohypoxanthine;Hypoxanthine, 8-mercapto-;Nsc22713
• CAS NO: 6305-94-8
• Molecular Formula: C₅H₄N₄OS
• Molecular Weight: 168.17646
• EINECS: 228-617-2
• Mol File: 6305-94-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 280.4°C at 760 mmHg
• Flash Point: 123.4°C
• Appearance: /
• Density: 2.08g/cm³
• Vapor Pressure: 0.0038mmHg at 25°C
• Refractive Index: 2.019
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,7,8,9-tetrahydro-8-thioxo-6H-purin-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,7,8,9-tetrahydro-8-thioxo-6H-purin-6-one(6305-94-8)
• EPA Substance Registry System: 1,7,8,9-tetrahydro-8-thioxo-6H-purin-6-one(6305-94-8)

Safety Data

• Hazardous Substances Data: 6305-94-8(Hazardous Substances Data)

Usage

Description

1,7,8,9-tetrahydro-8-thioxo-6H-purin-6-one, also known as 6-Hydroxy-8-mercaptopurine, is a thiopurine drug derived from the purine family of compounds. It is characterized by its unique chemical structure, which includes a thiol group attached to the purine ring. This structure endows it with specific properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
1,7,8,9-tetrahydro-8-thioxo-6H-purin-6-one is used as a potential substrate for thiopurine methyltransferase (TPMT) in the pharmaceutical industry. This application is due to its ability to interact with the enzyme, which plays a crucial role in the metabolism of thiopurine drugs. By serving as a substrate, it can help in understanding the enzyme's function and potentially contribute to the development of new therapeutic strategies for conditions that involve TPMT activity.
Used in Research and Development:
In the field of research and development, 1,7,8,9-tetrahydro-8-thioxo-6H-purin-6-one is used as a chemical intermediate for the synthesis of various biologically active compounds. Its unique structure makes it a valuable building block for the development of new drugs and pharmaceuticals, particularly those targeting purine-related pathways.
Used in Diagnostic Applications:
1,7,8,9-tetrahydro-8-thioxo-6H-purin-6-one can also be used in diagnostic applications, particularly in the development of assays and tests for the detection and measurement of thiopurine methyltransferase activity. By serving as a substrate in these assays, it can help researchers and clinicians evaluate the enzyme's function and its potential role in various diseases and conditions.

InChI:InChI=1/C5H4N4OS/c10-4-2-3(6-1-7-4)9-5(11)8-2/h1H,(H3,6,7,8,9,10,11)

Upstream product

• 1672-50-0 5,6-diamino-4(3H)-pyrimidinone 
• 17356-08-0 thiourea 
• 52502-66-6 5,6-diamino-3H-pyrimidin-4-one; sulfate 
• 118974-81-5 hypoxanthine 7-N-oxide 
• 75-15-0 carbon disulfide 

Downstream Products

• 68-94-0 hypoxanthine 
• 15986-30-8 8-benzylsulfanyl-1,7⁽⁹⁾-dihydro-purin-6-one 
• 1118887-99-2 C₂₇H₂₆Cl₃N₅O₆S 
• 2508-06-7 8-methylsulfanyl-7(9)H-purin-6-ylamine 
• 24079-37-6 Dithiopurine 
• 59008-14-9 8-methylsulfanyl-1,7⁽⁹⁾-dihydro-purin-6-one 
• 69341-06-6 (6-oxo-6,7-dihydro-1H-purin-8-ylmercapto)-acetic acid 

Relevant articles and documents

Imidazopyridine- and purine-thioacetamide derivatives: Potent inhibitors of nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1)

Nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1) belongs to the family of ecto-nucleotidases, which control extracellular nucleotide, nucleoside, and (di)phosphate levels. To study the (patho)physiological roles of NPP1 potent and selective inhibitors with drug-like properties are required. Therefore, a compound library was screened for NPP1 inhibitors using a colorimetric assay with p-nitrophenyl 5′-thymidine monophosphate (p-Nph-5′-TMP) as an artificial substrate. This led to the discovery of 2-(3H-imidazo[4,5-b]pyridin-2-ylthio)-N-(3,4-dimethoxyphenyl)acetamide (5a) as a hit compound with a Ki value of 217 nM. Subsequent structure-activity relationship studies led to the development of purine and imidazo[4,5-b]pyridine analogues with high inhibitory potency (Ki values of 5.00 nM and 29.6 nM, respectively) when assayed with p-Nph-5′-TMP as a substrate. Surprisingly, the compounds were significantly less potent when tested versus ATP as a substrate, with Ki values in the low micromolar range. A prototypic inhibitor was investigated for its mechanism of inhibition and found to be competitive versus both substrates.

Method for the selection of genetically transformed cells and compounds for use in the method

A method for selecting from a population of cells genetically transformed cells into which a desired nucleotide sequence has been introduced, wherein in the transformed cells the desired nucleotide sequence or a co-introduced nucleotide sequence induces or increases a positive effect of a compound or nutrient supplied to the population of cells, thereby allowing the transformed cells to be identified or selected from non-transformed cells, e.g. for the preparation of genetically transformed plants not containing as a selection marker a non-native nucleotide sequence coding for toxin, antibiotic or herbicide resistance; as well as novel glucuronide compounds, including cytokinin glucuronide compounds, for use in the method.