2508-06-7

Basic information

• Product Name: 8-(methylsulfanyl)-5H-purin-6-amine
• CAS NO: 2508-06-7
• Molecular Formula: C₆H₇N₅S
• Molecular Weight: 181.2183
• Mol File: 2508-06-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 344.1°C at 760 mmHg
• Flash Point: 161.9°C
• Density: 1.78g/cm³
• Vapor Pressure: 6.74E-05mmHg at 25°C
• Refractive Index: 1.892
• CAS DataBase Reference: 8-(methylsulfanyl)-5H-purin-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-(methylsulfanyl)-5H-purin-6-amine(2508-06-7)
• EPA Substance Registry System: 8-(methylsulfanyl)-5H-purin-6-amine(2508-06-7)

Safety Data

• Hazardous Substances Data: 2508-06-7(Hazardous Substances Data)

Usage

General Description

8-(methylsulfanyl)-5H-purin-6-amine is a chemical compound with the molecular formula C6H7N5S. It is a derivative of purine, a heterocyclic organic compound that is commonly found in nucleic acids, such as DNA and RNA. The compound contains a purine core with a methyl sulfanyl group attached at the 8th position and an amine group at the 6th position. 8-(methylsulfanyl)-5H-purin-6-amine has potential biological and pharmacological activities and may be used in pharmaceutical research and drug development.

Upstream product

• 100859-87-8 6-chloro-8-methylsulfanyl-7⁽⁹⁾H-purine 
• 7390-62-7 6-amino-7,9-dihydro-8H-purine-8-thione 
• 74-88-4 methyl iodide 
• 6305-94-8 8-thioxo-8,9-dihydro-1H-purin-6(7H)-one 
• 59008-14-9 8-methylsulfanyl-1,7⁽⁹⁾-dihydro-purin-6-one 
• 29836-02-0 8-(methylthio)-2'-deoxyadenosine 
• 33426-53-8 8-(methylthio)purine 
• 127133-08-8 2',3'-Dideoxy-8-methylthioadenosine 
• 6974-78-3 8-bromoadenine 

Downstream Products

• 303014-75-7 (S)-7-[(Trityloxy)methyl]-7,8-dihydro[1,3]oxazolo[3,2-e]purine-4-amine 
• 328381-23-3 (S)-3-[2-Hydroxy-3-(trityloxy)propyl]-8-(methylsulfanyl)adenine 
• 328381-25-5 (S)-9-[2-Hydroxy-3-(trityloxy)propyl]-8-(methylsulfanyl)adenine 

Relevant articles and documents

Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family

Adenine derivatives bearing substituents in the 2-, N6-, 7-, 8-, and/or 9-position and a series of deazapurines were synthesized and investigated in [3H]adenine binding studies at the adenine receptor in rat brain cortical membrane preparations (rAde1R). Steep structure-activity relationships were observed. Substitution in the 8-position (amino, dimethylamino, piperidinyl, piperazinyl) or in the 9-position (2-morpholinoethyl) with basic residues or introduction of polar substituents at the 6-amino function (hydroxy, amino, acetyl) represented the best modifications. Functional evaluation of selected adenine derivatives in adenylate cyclase assays at 1321N1 astrocytoma cells stably expressing the rAde1R showed that all compounds investigated were agonists or partial agonists. A subset of compounds was additionally investigated in binding studies at human embryonic kidney (HEK293) cells, which also express a high-affinity adenine binding site. Structure-affinity relationships at the human cell line were similar to those at the rAde1R, but not identical. In particular, N 6-acetyladenine (25, Ki rat: 2.85 μM; Ki human: 0.515 μM) and 8-aminoadenine (33, Ki rat: 6.51 μM; Ki human: 0.0341 μM) were much more potent at the human as compared to the rat binding site. The new AdeR ligands may serve as lead structures and contribute to the elucidation of the functions of the adenine receptor family. 2009 American Chemical Society.

Hydrolysis of 2'-Deoxypurine Nucleosides. The Effect of Substitution at the C-8 Position.

The hydrolytic stability of 2'-deoxypurine nucleosides is decreased by introduction of electronwithdrawing substituents at the C-8 position in the series of compounds 2-8, 10-14.The sulfone group causes a 2.9 x 104 rate acceleration for glycosidic, bond cleavage in compound 14.

The behaviour of 6- and 8-substituted purines toward potassium amide in liquid ammonia. A new example of tele-amination

Reaction of 6-chloro- and 6-(methylthio)purine with potassium amide in liquid ammonia leads to the formation of adenine.When these aminations are carried out with 15N-labelled potassium amide, the 15N label is found to be present in the amino group, proving that these reactions do not involve opening of the pyrimidine ring.Low temperature 1H- and 13C-NMR spectroscopy of solutions of 6-chloro- and 6-(methylthio)purine in liquid ammonia, containing potassium amide give no evidence for the presence of an intermediary ?-adduct. 8-Chloro- and 8-(methylthio)purine undergo a Tschitschibabin amination at position 6 leading to 8-chloro- an d 8-(methylthio)adenine.In addition 8-chloropurine gives adenine.Evidence is presented that the formation of this product proceeds via a tele-amination. 6-tert-Butyl-8-(methylthio)purine and 8-aminopurine are found to be unreactive towards potassium amide.