5417-84-5

Usage

Uses

Used in Oncology:
6-Ethylmercaptopurine is utilized as an anticancer drug for the treatment of acute leukemia. It is employed to inhibit the rapid cell division characteristic of leukemia, thereby controlling the disease progression.
Used in Gastroenterology:
In the field of gastroenterology, 6-Ethylmercaptopurine serves as an anti-inflammatory agent for inflammatory bowel disease. It reduces inflammation in the intestines by dampening the immune response and the associated cellular proliferation.
However, due to its potential toxic effects on the bone marrow and liver, and its ability to increase the risk of infection, 6-Ethylmercaptopurine requires close monitoring of blood cell counts and liver function during treatment. This ensures the safe and effective application of the medication, balancing its therapeutic benefits against potential adverse effects.

InChI:InChI=1/C7H8N4S/c1-2-12-7-5-6(9-3-8-5)10-4-11-7/h3-5H,2H2,1H3

Upstream product

• 87-42-3 6-chloropurine 
• 75-08-1 ethanethiol 
• 74-96-4 ethyl bromide 
• 157930-09-1 6-Mercaptopurine 
• 87-42-3 6-chloro-7H-purine 
• 50-44-2 6H-purine-6-thione 
• 75-03-6 ethyl iodide 

Downstream Products

• 82499-11-4 6-ethylsulfonylpurine 

Relevant academic research and scientific papers

Pd/PTABS: Low-Temperature Thioetherification of Chloro(hetero)arenes

The thioetherification of heteroaryl chlorides is an essential synthetic methodology that provides access to bioactive drugs and agrochemicals. Due to their (actual or potential) industrial importance, the development of efficient and low-temperature protocols for accessing these compounds is a requirement for economic and ecologic reasons. A particular highly effective catalytic protocol using the Pd/PTABS system at only 50 °C was developed accordingly. The coupling between chloroheteroarenes and a variety of less reactive arylthiols and alkylthiols was carried out with a high efficiency. Heteroarenes of commercial relevance such as purines and pyrimidines were also found to be useful substrates for the reported transformation. The commercial drug Imuran (azathioprine) was synthesized as an example, and its preparation could be optimized. DFT studies were performed to understand the electronic effects of the tested ligands on the catalytic reaction.

The discovery of purine-based agents targeting triple-negative breast cancer and the αB-crystallin/VEGF protein–protein interaction

Oestrogen receptor-negative breast cancer, particularly subtypes such as triple-negative breast cancer (TNBC, around 10–15% of cases), are characterised by poor long-term survival, poor response to therapy and early progression to metastasis. Purine-based compounds represent a privileged scaffold in anticancer drug design, with several clinically approved and experimental agents in clinical development comprising a purine core structure. In this study, a series of new purine-based compounds were synthesised; seven of the new analogues were found to significantly reduce the in vitro viability of TNBC cell lines (MDA-MB-231 and MDA-MB-436) with IC50 values of ≤50 μM. In previous work, we have proposed a new concept for targeting angiogenesis driving TNBC progression, by disrupting the protein–protein interaction between the molecular chaperone αB-crystallin (CRYAB) and VEGF. Since previous clinical studies applying anti-VEGF therapy to TNBC patients have met with limited success, we were interested to test our most promising purine analogues against CRYAB/VEGF, using a custom-designed cell-based CRYAB/VEGF165 interaction assay platform. Analogues 4e and 4f significantly reduced the interaction between CRYAB/VEGF165, and compound 4e (100 μM) was also found to decrease the levels of soluble VEGF expressed by MDA-MB-231 cells by 40%. In conclusion, these promising early activity profiles warrant further investigation to validate this concept.