6-Methylthioguanine

Base Information

• Chemical Name: 6-Methylthioguanine
• CAS No.: 1198-47-6
• Molecular Formula: C6H7N5S
• Molecular Weight: 181.221
• Hs Code.: 29335995
• European Community (EC) Number: 214-833-4
• NSC Number: 29420
• UNII: QNV75HJN3A
• DSSTox Substance ID: DTXSID60152594
• Nikkaji Number: J124.095A
• Wikidata: Q74417248
• ChEMBL ID: CHEMBL1172777
• Mol file: 1198-47-6.mol

Synonyms:6-methylthioguanine;S6-methylthioguanine

Chemical Property of 6-Methylthioguanine

Chemical Property:

• Appearance/Colour: off-white crystalline powder
• Vapor Pressure: 6.74E-05mmHg at 25°C
• Melting Point: 234-237oC
• Refractive Index: 1.892
• Boiling Point: 622.1 °C at 760 mmHg
• Flash Point: 330 °C
• PSA: 105.78000
• Density: 1.55 g/cm³
• LogP: 1.23820
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 181.04221642
• Heavy Atom Count: 12
• Complexity: 166

Purity/Quality:

98% ^*data from raw suppliers

6-Methylthioguanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 24/25-39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CSC1=NC(=NC2=C1NC=N2)N
• Uses: As a metabolite of 2’-Deoxy-6-thio Guanosine (D281650) and 6-Thioguanine, 6-Methylthioguanine can be used as an effective immunosuppressant and anticancer agent, however chronic exposure can be mutagenic in human cells as long-term use of thiopurines was found to be associated with a significantly increased risk of various types of cancer. 2-Amino-6-methylmercaptopurine is a 2-amino-6-alkyldithiopurine that has been used with other 6-position carbon analogues to study brain specific diazepam binding.

Technology Process of 6-Methylthioguanine

There total 5 articles about 6-Methylthioguanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2-Amino-6-chloropurin (10310-21-1) + sodium thiomethoxide (5188-07-8) → 2-amino-6-(methylsulfanyl)purine (1198-47-6)

Guidance literature:

In 1-methyl-pyrrolidin-2-one; at 90 ℃; for 0.0166667h; microwave irradiation;

DOI:10.1016/j.tet.2007.02.124

Reference yield:

S-(5′-adenosyl)-L-methionine chloride + 6-thioguanine (154985-75-8,155021-73-1,153981-51-2,153981-52-3,153981-53-4,153981-54-5,153981-55-6,153981-56-7,153981-57-8,153981-58-9,153981-59-0,154034-61-4,154034-62-5) → 2-amino-6-(methylsulfanyl)purine (1198-47-6)

Guidance literature:

With human thiopurine S-methyltransferase expressed in yeast; tris hydrochloride; at 21.5 ℃; for 1h; pH=7.4; Enzyme kinetics; Enzymatic reaction;

Reference yield:

→ 2-amino-6-(methylsulfanyl)purine (1198-47-6)

Guidance literature:

6-Methylthio-2.4.5-triaminopyrimidin, Orthoameisensaeureaethylester, Acetanhydrid (sied.);

DOI:10.1021/ja01495a060

upstream raw materials:

thioguanin

dimethyl sulfate

methyl iodide

6-thioguanine

Downstream raw materials:

N⁶-benzyl-7⁽⁹⁾H-purine-2,6-diyldiamine

2-Amino-6-hydrazino-7H-purine

7-methylguanine

(2R,3R,4S,5R)-2-[2-amino-6-(methylthio)-9H-purin-9-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

Refernces

• 1、 Huang, Ling-Kuen,Cherng, Yen-Chih,Cheng, Yann-Ru,Jang, Jing-Pei,Chao, Yi-Ling,Cherng, Yie-Jia. "An efficient synthesis of substituted cytosines and purines under focused microwave irradiation". . p. 5323 - 5327. Retrieved 2008/02/01.