39576-56-2

Upstream product

• 88-74-4 2-nitro-aniline 
• 273-09-6 benzofurazan 
• 5042-53-5 1-(phenylsulfanyl)acetone 
• 480-96-6 benzofurazan oxide 

Downstream Products

• 40735-42-0 2-benzenesulfonyl-3-methyl-quinoxaline 1,4-dioxide 

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.

Novel substituted quinoxaline 1,4-dioxides with in vitro antimycobacterial and anticandida activity

Thirty-six 6(7)-substituted-3-methyl- or 3-halogenomethyl-2-phenylthio-phenylsulphonyl-chloro-quinoxaline 1,4-dioxides belonging to series 3-6 were synthesised and submitted to a preliminary in vitro evaluation for antimycobacterial, anticandida and antibacterial activities. Antitubercular screening showed a generally good activity of 3-methyl-2-phenylthioquinoxaline 1,4-dioxides (3d,e,h-j) against Mycobacterium tuberculosis, and exhibited MIC between 0.39 and 0.78 μg mL-1 (rifampicin MIC=0.25 μg mL-1), whereas in compounds 4d,e, 5a,b,d,e,l and 6b-e,j,l MIC ranged between 1.56 and 6.25 μg mL-1. Results of the antibacterial and anticandida screening showed that 6e and 6l exhibited MIC=0.4 and 1.9 μg mL-1, respectively, against Candida krusei (miconazole MIC=0.9 μg mL-1), and 4i, 5b,d, 6e, MIC=3.9 μg mL-1 against Candida glabrata (miconazole MIC=0.4 μg mL-1), while compounds 3d,l, 5e,l, and 6b,d,e,l showed MIC=15.6 μg mL-1 against Vibrio alginolyticus.