3324-79-6

Usage

Uses

Used in Oncology:
7-Methyl-6-mercaptopurine is used as an anticancer agent for the treatment of certain types of cancers, such as leukemia and lymphoma. Its mechanism of action involves inhibiting the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRT), which leads to a reduction in purine synthesis, thereby disrupting the rapid cell division typical of cancerous cells.
Used in Autoimmune Disease Treatment:
Leveraging its immunosuppressive and anti-inflammatory properties, 7-Methyl-6-mercaptopurine is used in the management of autoimmune diseases. By modulating the immune response, 7-METHYL-6-MERCAPTOPURINE can help alleviate symptoms and potentially induce remission in conditions where the body's immune system mistakenly attacks its own tissues.
Used in Pharmaceutical Development:
As a purine analog, 7-Methyl-6-mercaptopurine serves as a valuable compound in pharmaceutical research and development. Its unique properties make it a candidate for the creation of new drugs targeting a variety of diseases, including those beyond cancer and autoimmune disorders, where modulation of purine synthesis or immune response is beneficial.

InChI:InChI=1/C6H6N4S/c1-10-3-9-5-4(10)6(11)8-2-7-5/h2-3H,1H3,(H,7,8,11)

Upstream product

• 5440-17-5 6-chloro-7-methyl-7H-purine 
• 17356-08-0 thiourea 
• 1006-08-2 7-methyl-1,7-dihydro-purin-6-one 
• 302840-04-6 7-methyl-6-[(1-methyl-4-nitro-5-imidazolyl)thio]purine 
• 446-86-6 azathioprine 
• 110475-17-7 5-amino-3-methyl-3H-imidazole-4-carboxylic acid amide; hydrochloride 
• 304441-05-2 9-acetyl-6-[(1-methyl-4-nitro-5-imidazolyl)thio]purine 

Downstream Products

• 6334-43-6 6-ethylmercapto-7-methyl-7H-purine 
• 935-69-3 7-methyladenine 

Relevant academic research and scientific papers

Chemical transformations of 6-[(1-methyl-4-nitro-5-imidazolyl)-thio]purine (azathioprine)

The chemical transformations of 6-[(1-methyl-4-nitro-5-imidazolyl)thio]purine (azathiopurine)- hydrogenation, acetylation, alkylation by lower alkyl halides at positions 7 and 9 of the purine ring, hydrolytic cleavage at the C(6)-S and S-C(5) bonds - were studied.

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.

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.

Regioselective and efficient synthesis of N 7-substituted adenines, guanines, and 6-mercaptopurines

A simple and efficient protocol for the preparation of N 7-substituted adenines, guanines, and 6-mercaptopurines is described. The key step is the regioselective preparation of 7-substituted 6-chloropurines which are building blocks for the div