91658-79-6

Usage

Uses

Used in Pharmaceutical Industry:
3-(2-aminophenyl)quinoxalin-2(1H)-one is used as a lead compound for drug development due to its demonstrated anti-inflammatory, anticancer, and antimicrobial properties. Its multifaceted biological activities make it a promising candidate for the treatment of various diseases and conditions.
Used in Research and Development:
In the scientific community, 3-(2-aminophenyl)quinoxalin-2(1H)-one serves as a subject of study for understanding its synthesis, characterization, and the exploration of its chemical and physical properties. This research aids in optimizing its potential use in pharmaceutical formulations and therapeutic interventions.

Upstream product

• 91-56-5 indole-2,3-dione 
• 95-54-5 1,2-diamino-benzene 
• 91658-85-4 N-(2-(3-oxo-3,4-dihydroquinoxalin-2-yl)phenyl)acetamide 

Downstream Products

• 91658-85-4 N-(2-(3-oxo-3,4-dihydroquinoxalin-2-yl)phenyl)acetamide 
• 243-59-4 indophenazine 
• 64819-77-8 2-methyl-4-(benzimidazol-2-yl)quinoline 
• 1620149-52-1 2-(3-bromophenyl)-4-(benzimidazol-2-yl)quinoline 
• 1620149-51-0 2-(4-bromophenyl)-4-(benzimidazol-2-yl)quinoline 
• 42039-62-3 2-phenyl-4-(benzimidazol-2-yl)quinoline 
• 1620149-55-4 2-(2-chlorophenyl)-4-(benzimidazol-2-yl)quinoline 
• 1620149-54-3 2-(4-chlorophenyl)-4-(benzimidazol-2-yl)quinoline 
• 1620149-53-2 2-(2-bromophenyl)-4-(benzimidazol-2-yl)quinoline 
• 1265681-40-0 3-(2',4'-diaminoazobenzene-2-yl)quinoxalin-2(1H)-one 
• 777094-05-0 3-[2-amino-3-(3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-yl)phenyl]-2,3-dihydro-quinoxalin-2-one 
• 647027-08-5 2-{[2-(3-oxo-3,4-dihydro-quinoxalin-2-yl)-phenyl]-hydrazono}-malononitrile 
• 777094-02-7 3-[2-(2-oximinoacetylamino)phenyl]-1,2-dihydro-quinoxalin-2-one 
• 1504-78-5 3-phenylquinoxaline-2(1H)-one 

Relevant academic research and scientific papers

Facile synthesis of quinoxaline annulated perfluoroalkylated benzoazepine derivatives

Novel perfluoroalkylated benzoazepinoquinoxaline derivatives were synthesized by consecutive intermolecular Michael addition and intramolecular cyclization from 3-(2-aminophenyl)quinoxalin-2(1H)-ones and methyl perfluoroalk-2-ynoates in good yields. This

A potent and selective quinoxalinone-based STK33 inhibitor does not show synthetic lethality in KRAS-dependent cells

The KRAS oncogene is found in up to 30% of all human tumors. In 2009, RNAi experiments revealed that lowering mRNA levels of a transcript encoding the serine/threonine kinase STK33 was selectively toxic to KRAS-dependent cancer cell lines, suggesting that small-molecule inhibitors of STK33 might selectively target KRAS-dependent cancers. To test this hypothesis, we initiated a high-throughput screen using compounds in the Molecular Libraries Small Molecule Repository (MLSMR). Several hits were identified, and one of these, a quinoxalinone derivative, was optimized. Extensive SAR studies were performed and led to the chemical probe ML281 that showed low nanomolar inhibition of purified recombinant STK33 and a distinct selectivity profile as compared to other STK33 inhibitors that were reported in the course of these studies. Even at the highest concentration tested (10 μM), ML281 had no effect on the viability of KRAS-dependent cancer cells. These results are consistent with other recent reports using small-molecule STK33 inhibitors. Small molecules having different chemical structures and kinase-selectivity profiles are needed to fully understand the role of STK33 in KRAS-dependent cancers. In this regard, ML281 is a valuable addition to small-molecule probes of STK33.

Synthesis of substituted pyrazino[5,6-b]pyrimidine and some indole derivatives

Refluxing dimethyl acetylenedicarboxylate (DMAD) or 1,2-dibenzoylacetylene with isatin-3-thiosemicarbazone or isatin-3-thiocarbohydrazone in methanol produced 3-substituted oxindoles in good yields. Reaction of equimolecular amounts of 5,6-diamino-urasil-

Studies of the reactions between indole-2,3-diones (isatins) and 2-aminobenzylamine

Reflux of equimolecular amounts 2-aminobenzylamine and isatins in acetic acid produced indolo[3,2-c]quinolin-6-ones in good yields. A proposed mechanism involving initial formation of a spiro compound is given. This isolable intermediate subsequently rearranges via a sequential isocyanate ring opening and a cyclisation process to a urea derivative which finally cyclized to the indolo[3,2-c]quinolin-6-ones. The urea derivative could be prepared separately and cyclized selectively to indolo[3,2-c]quinolin-6-one. Reaction of N-acetylisatin with 2-aminobenzylamine at room temperature yielded the 1,4-benzodiazepinone 3-(2-acetamidophenyl)-1,5-dihydro-1,4-benzodiazepin-2-one whereas its isomer 2(2-acetamidophenyl)-4,5-dihydro-1,4-benzodiazepin-3-one was obtained from 2-(2-acetylaminophenyl)-N-(2-aminobenzyl)-2-oxoacetamide in acetic acid at room temperature. The previously unknown linear isomer of indolo[3,2-c]quinolin-6-one, i.e. indolo[2,3-b]quinolin-11-one, has been prepared by thermal (260°C) cyclization of methyl 2-phenylamino indole-3-carboxylate, which in turn was prepared in two steps from methyl indole-3-carboxylate.

REACTION OF o-PHENYLENEDIAMINE WITH ISATINS

It is shown that the reaction of o-phenylenediamine with isatins in the general case leads to mixtures of indoloquinoxalines, 3-(2'-aminophenyl)-2(1H)-quinoxalinones, and spiro.Spiro2H-benzimidazole-2,3'-in