73148-15-9

Usage

Uses

Used in Pharmaceutical Industry:
6,7-dichloro-3-methyl-3,4-dihydroquinoxalin-2(1H)-one is utilized as a pharmaceutical agent for its potential anti-microbial properties, serving as a candidate for treating various microbial infections. Its ability to target and inhibit microbial growth makes it a promising candidate for further research and development in this field.
Used in Anticancer Research:
In the realm of oncology, 6,7-dichloro-3-methyl-3,4-dihydroquinoxalin-2(1H)-one is employed as an anti-cancer agent, being investigated for its potential to combat cancer cells. Its mechanism of action and efficacy against different types of cancer are under study, with the aim of identifying its role in cancer treatment.
Used in Anti-inflammatory Applications:
6,7-dichloro-3-methyl-3,4-dihydroquinoxalin-2(1H)-one is also being explored for its anti-inflammatory capabilities. It is used as an agent to reduce inflammation, which could have implications for treating a variety of inflammatory conditions.
Used in Anti-malarial Drug Development:
6,7-dichloro-3-methyl-3,4-dihydroquinoxalin-2(1H)-one is being investigated for its potential as an anti-malarial agent, with research focusing on its ability to combat the Plasmodium parasites responsible for malaria. This application could lead to the development of new treatments for this widespread disease.
Used in Research as a Building Block:
6,7-dichloro-3-methyl-3,4-dihydroquinoxalin-2(1H)-one serves as a valuable building block in the synthesis of other bioactive compounds. Its chemical properties make it a useful component in creating new molecules with potential therapeutic applications, thus contributing to the advancement of drug discovery.

InChI:InChI=1/C9H8Cl2N2O/c1-4-9(14)13-8-3-6(11)5(10)2-7(8)12-4/h2-4,12H,1H3,(H,13,14)

Upstream product

• 617-35-6 2-oxo-propionic acid ethyl ester 
• 5348-42-5 4,5-Dichloro-1,2-phenylenediamine 
• 600-22-6 pyruvic acid methyl ester 
• 127-17-3 2-oxo-propionic acid 
• 2339-78-8 1,2-dichloro-4-fluoro-5-nitrobenzene 

Downstream Products

• 216436-74-7 6,7-Dichloro-3-(3,5-diphenyl-furan-2-yl)-1H-quinoxalin-2-one 
• 216436-73-6 6,7-Dichloro-3-(4-oxo-2-phenyl-4-pyridin-4-yl-butyl)-1H-quinoxalin-2-one 
• 216436-75-8 6,7-Dichloro-3-(3-phenyl-5-pyridin-4-yl-furan-2-yl)-1H-quinoxalin-2-one 
• 149366-37-0 6,7-dichloro-3-styrylquinoxaline-2(1H)-one 

Relevant academic research and scientific papers

Styryl-containing quinoxalinone derivatives and preparation method thereof

The invention belongs to the technical field of medicinal chemistry, and particularly relates to styryl-containing quinoxalinone derivatives and a preparation method thereof, and the structure of thesynthesized compound is shown as the following formula I

Benzhydrazide skeleton-containing derivative, preparation method thereof, and application thereof to preparation of anti-tumor medicines

The invention provides a benzhydrazide skeleton-containing derivative, a preparation method thereof, and application thereof to preparation of anti-tumor medicines. The structural formula of the benzhydrazide skeleton-containing derivative is shown in a formula X (the formula X is shown in the description); and R is selected from hydrogen, halogen, alkyl, nitryl, alkoxy and halogenated alkyl. Thepreparation method comprises the step of performing reaction on benzhydrazide and a quinoxaline to prepare the benzhydrazide skeleton-containing derivative. The benzhydrazide skeleton-containing derivative has a remarkable inhibition effect on cervical cancer cells (Hela), lung carcinoma cells (A549), melanoma cells (F10) and hepatoma carcinoma cells (HepG2). The benzhydrazide skeleton-containingderivative is obtained by effectively integrating pharmacophores quinoxaline and hydrazide. The synthesis method is high in repeatability, high in stability and simple in reaction condition; furthermore, the experiment environment is mild, the yield is high and mass production can be conducted under the condition of small investment.

Citric acid: An efficient and green catalyst for rapid one pot synthesis of quinoxaline derivatives at room temperature

The condensation of o-phenylenediamines with 1,2-dicarbonyl compounds in the presence of citric acid afforded the corresponding quinoxaline derivatives in higher yields at room temperature in ethanol, and most of the reactions were completed in less than 1 min.

Crystal structures of 3-methyl-2(1H)-quinoxalinone and three substituted derivatives

3-Methyl-2(1H)-quinoxalinone and three derivatives (3,7-dimethyl-2(1H)- quinoxalinone, 3-methyl-6,7-dichloro-2(1H)-quinoxalinone and 3-methyl-7-nitro-2(1H)-quinoxalinone) have been synthesised and analysed by 1H NMR and IR spectral spectroscopies. The crystal structures have been determined at room temperature from X-ray single crystal diffraction data for three of them and from powder diffraction data for the nitro derivative. 3-Methyl-2(1H)-quinoxalinone crystallises in the P21/c monoclinic system, 3,7-dimethyl-2(1H)-quinoxalinone in the Pbca orthorhombic system and the two others compounds in the P1 triclinic system. For the nitro derivative, C-H..N short contacts are established between the carbon of the methyl and the double bounded nitrogen of the ring. For the three other compounds N-H..O hydrogen bonds involve the atoms of the heterocyclic ring. Copyright

Revisiting the Hinsberg reaction: Facile and expeditious synthesis of 3-substituted quinoxalin-2(1H)-ones under catalyst-free conditions in water

Substituted benzene-1,2-diamine reacted with various α-keto esters at 50° under mild conditions for 15 min using H2O as reaction medium, providing a variety of 3-substituted quinoxalinone derivatives in excellent yields. The reaction was instantaneous, and products were isolated by simple filtration.

Fragment based design of new H4 receptor-ligands with anti-inflammatory properties in vivo

Using a previously reported flexible alignment model we have designed, synthesized, and evaluated a series of compounds at the human histamine H 4 receptor (H4R) from which 2-(4-methyl-piperazin-l-yl)- quinoxaline (3) was identified as a new lead structure for H4R ligands. Exploration of the structure-activity relationship (SAR) of this scaffold led to the identification of 6,7-dichloro 3-(4-methylpiperazin-l-yl) quinoxalin-2(1H)-one (VUF 10214, 57) and 2-benzyl-3-(4-methyl-piperazin-l-yl) quinoxaline (VUF 10148, 20) as potent H4R ligands with nanomolar affinities. In vivo studies in the rat reveal that compound 57 has significant anti-inflammatory properties in the carrageenan-induced paw-edema model.

Solid-phase traceless synthesis of selected nitrogen-containing heterocyclic compounds. The encore technique for directed sorting of modular solid support

The acid lability of electron-rich N-benzylanilines has been exploited in a linker for the traceless solid-phase synthesis of benzimidazoles, 2-aminobenzimidazoles, quinoxalinones and tetrahydroquinoxalines. The target compound precursors were assembled o

A solid phase traceless synthesis of quinoxalinones

A solid-phase traceless synthesis of quinoxalinones in three combinatorial steps is reported. An aldehyde functionalized polystyrene resin was reductively alkylated by amino acid methyl esters, and then the resin bound secondary amines were reacted with o

Synthesis of new ethyl 4-[3-(Dimethylamino)-propylmethylamino]pyrrolo[1,2-α]quinoxaline-2-carboxylate derivatives and preliminary CNS pharmacological evaluation in mice

The synthesis of new ethyl 4-[3-(dimethylamino)propylmethylamino]pyrrolo[1,2-α]-quinoxaline-2- carboxylate derivatives is described. Proconvulsant, convulsant and anticonvulsant activities were observed. Structure activity relationships are discussed.

A novel synthesis of 2-(2-quinoxalino)-3,5-diarylfurans

A short synthesis of 2-(2-quinoxalino)-3,5-diarylfurans, allowing the stepwise introduction of the aromatic rings, is designed and implemented utilizing the DDQ promoted cyclization of 4-(2-quinoxalino)-1,3- diarylbutanones as the key transformation.