77186-62-0

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-3-ethylquinoxaline is used as a chemical intermediate for the synthesis of various drugs and bioactive molecules. Its incorporation into the molecular structures of these compounds can enhance their therapeutic effects and pharmacological properties, contributing to the development of novel pharmaceuticals.
Used in Drug Development:
As a versatile building block, 2-chloro-3-ethylquinoxaline is utilized in the design and synthesis of new drug compounds. Its unique structure allows for the creation of molecules with specific biological activities, making it a valuable component in the advancement of pharmaceutical research and drug discovery.

InChI:InChI=1/C10H9ClN2/c1-2-7-10(11)13-9-6-4-3-5-8(9)12-7/h3-6H,2H2,1H3

Upstream product

• 13297-35-3 3-ethyl-3,4-dihydroquinoxalin-2(1H)-one 
• 63186-18-5 ethyl 2-(3,4-dihydro-3-oxo-2-quinoxalinyl)propanoate 
• 95-54-5 1,2-diamino-benzene 

Downstream Products

• 1427029-37-5 1-(2-chlorophenyl)-4-ethyl-[1,2,4]triazolo[4,3-a]quinoxaline 

Relevant academic research and scientific papers

Synthesis of 2-(Quinoxalin-2-ylamino-benzotriazolyl) Pentanedioic Derivatives as Potential Anti-Folate Agents

Anti-folate agents had a significant impact on therapeutic treatment plans for diseases such as cancer, and bacterial and parasitic infections, notably malaria. Quinoxaline derivatives showed in vitro anticancer activity and were able to inhibit both the dihydrofolate reductase and thymidylate synthase. Here, we decided to combine the chemical properties of quinoxalines and quinoxaline 1,4-dioxides with those of benzotriazole nucleus with the aim to evaluate the resulting biological properties. Two main new series, including more than 60 compounds, were prepared. In the first one, the benzotriazole moiety was linked through the nitrogen atoms 1, 2, or 3, to a glutaric acid substituent to simulate a glutamic moiety. In the second series, the glutaric acid was substituted with acetic acid moiety to evaluate the effects of steric hindrance. Here, we describe the multistep chemical processes to obtain all titled quinoxalines starting from commercially available diamines. The classical oxidation of selected quinoxalines was unsuccessful, and we have come to an independent synthetic pathway to obtain new derivatives linked to the benzotriazole moieties starting from synthons bearing N-oxide functionality.

Structure-Activity Relationships of Quinoxaline-Based 5-HT3A and 5-HT3AB Receptor-Selective Ligands

Until recently, discriminating between homomeric 5-HT3A and heteromeric 5-HT3AB receptors was only possible with ligands that bind in the receptor pore. This study describes the first series of ligands that can discriminate between these receptor types at the level of the orthosteric binding site. During a recent fragment screen, 2-chloro-3-(4-methylpiperazin-1-yl)quinoxaline (VUF10166) was identified as a ligand that displays an 83-fold difference in [3H]granisetron binding affinity between 5-HT3A and 5-HT3AB receptors. Fragment hit exploration, initiated from VUF10166 and 3-(4-methylpiperazin-1-yl)quinoxalin-2-ol, resulted in a series of compounds with higher affinity at either 5-HT3A or 5-HT3AB receptors. These ligands reveal that a single atom is sufficient to change the selectivity profile of a compound. At the extremes of the new compounds were 2-amino-3-(4-methylpiperazin-1-yl)quinoxaline, which showed 11-fold selectivity for the 5-HT3A receptor, and 2-(4-methylpiperazin-1-yl)quinoxaline, which showed an 8.3-fold selectivity for the 5-HT3AB receptor. These compounds represent novel molecular tools for studying 5-HT3 receptor subtypes and could help elucidate their physiological roles.