55686-95-8

Usage

Uses

Used in Pharmaceutical Industry:
QUINOXALINE, 2,3-DICHLORO-6-(TRIFLUOROMETHYL)is used as a pharmaceutical compound for its potential antimicrobial, antifungal, and antitumor properties.
Used in Agricultural Industry:
QUINOXALINE, 2,3-DICHLORO-6-(TRIFLUOROMETHYL)is used as a herbicide and insecticide due to its herbicidal and insecticidal effects, making it a valuable compound for the development of new chemical pesticides.
Used in Organic Electronic Materials:
QUINOXALINE, 2,3-DICHLORO-6-(TRIFLUOROMETHYL)is used in the development of organic light-emitting diodes and solar cells for its potential use in organic electronic materials.

Upstream product

• 55687-31-5 Lilly 72525 
• 55687-31-5 2,3-dihydroxy-6-trifluoromethylquinoxaline 
• 368-71-8 4-(trifluoromethyl)-1,2-phenylenediamine 
• 400-98-6 4-trifluoromethyl-2-nitroaniline 
• 10026-13-8 phosphorus pentachloride 

Downstream Products

• 55686-97-0 6-(trifluoromethyl)-3-(phenylthio)-2-chloroquinoxaline 
• 1310877-48-5 (2E,2'E)-3,3'-(((6-(trifluoromethyl)quinoxaline-2,3-diyl)bis-(azanediyl))bis(4,1-phenylene))diacrylic acid 
• 1261078-48-1 (2E,2'E)-diethyl 3,3'-(((6-(trifluoromethyl)quinoxaline-2,3-diyl)bis(azanediyl))bis(4,1-phenylene))diacrylate 

Relevant academic research and scientific papers

Synthesis of 9-(trifluoromethyl)pyrido[1',2':1,2]-imidazo[4,5-b]quinoxalines

9-(Trifluoromethyl)pyrido[1',2':1,2]imidazo[4,5-b]quinoxalines (9-CF3-PIQs) were obtained from the cyclization of 2-amino-3-chloro-6-(trifluoromethyl)quinoxaline (1a) with some substituted pyridines. 3-[2(4-pyridyl)ethenyl]-9-CF3-PIQ, one of thus obtained 9-CF3-PIQs, cyclized with another molecule of 1a to produce the dihydro bis-PIQ-ethene derivative.

A One-pot Facile Synthesis of 2,3-Dihydroxyquinoxaline and 2,3-Dichloroquinoxaline Derivatives Using Silica Gel as an Efficient Catalyst

An efficient one-pot reaction has been developed for the synthesis of 2,3-dichloroquinoxaline derivatives 3a–n. The reaction was performed in two steps via a silica gel catalyzed tandem process from o-phenylenediamine and oxalic acid, followed by addition of phosphorus oxychloride (POCl3). A variety of 2,3-dichloroquinoxalines have been obtained in good to excellent overall yields. Eight known compounds 3a–3h were characterized by IR, 1H-NMR, and mass spectroscopies. Compounds 3i–3n without spectroscopic data were characterized by IR, 1H-NMR, 13C-NMR, and mass spectroscopies.

A new small molecule inhibitor of soluble guanylate cyclase

Soluble guanylate cyclase (sGC) is a haem containing enzyme that regulates cardiovascular homeostasis and multiple mechanisms in the central and peripheral nervous system. Commonly used inhibitors of sGC activity act through oxidation of the haem moiety, however they also bind haemoglobin and this limits their bioavailability for in vivo studies. We have discovered a new class of small molecule inhibitors of sGC and have characterised a compound designated D12 (compound 10) which binds to the catalytic domain of the enzyme with a KD of 11 μM in a SPR assay.

HETEROCYCLIC INHIBITORS OF HISTAMINE RECEPTORS FOR THE TREATMENT OF DISEASE

The present invention relates to compounds and methods which may be useful as inhibitors of H1R and/or H4R for the treatment or prevention of inflammatory, autoimmune, allergic, and ocular diseases.

Design and synthesis of small molecule RhoA inhibitors: A new promising therapy for cardiovascular diseases?

RhoA is a member of Rho GTPases, a subgroup of the Ras superfamily of small GTP-binding proteins. RhoA, as an important regulator of diverse cellular signaling pathways, plays significant roles in cytoskeletal organization, transcription, and cell-cycle progression. The RhoA/ROCK inhibitors have emerged as a new promising treatment for cardiovascular diseases. However, to date, RhoA inhibitors are macromolecules, and to our knowledge, small molecular-based inhibitors have not been reported. In this study, a series of first-in-class small molecular RhoA inhibitors have been discovered by using structure-based virtual screening in conjunction with chemical synthesis and bioassay. Virtual screening of ～200,000 compounds, followed by SPR-based binding affinity assays resulted in three compounds with binding affinities to RhoA at the micromolar level (compounds 1-3). Compound 1 was selected for further structure modifications in considering binding activity and synthesis ease. Fourty-one new compounds (1, 12a-v, 13a-h, and 14a-j) were designed and synthesized accordingly. It was found that eight (12a, 12j, 14a, 14b, 14d, 14e, 14 g, and 14h) showed high RhoA inhibition activities with IC50 values of 1.24 to 3.00 μM. A pharmacological assay indicated that two compounds (14g and 14 h) demonstrated noticeable vasorelaxation effects against PE-induced contraction in thoracic aorta artery rings and served as good leads for developing more potent cardiovascular agents.

FUSED TRICYCLIC COMPOUNDS WITH ADENOSINE A2a RECEPTOR ANTAGONIST ACTIVITY

The present invention relates to certain certain fused tricyclic heteroaryl rings compounds of the Formula (I) (also referred to herein as the "Fused Tricyclic Compounds"), wherein M, Q, U, W, X, Y, Z, R1, R2, and R3, and rings C and D are as herein described. The present invention also provides compositions comprising at least one Fused Tricyclic Compound, and use of such compounds in the treatment of central nervous system diseases or disorders such as Parkinson's disease.

HETEROCYCLIC INHIBITORS OF HISTAMINE RECEPTORS FOR THE TREATMENT OF DISEASE

The present invention relates to compounds and methods which may be useful as inhibitors of H1R and/or H4R for the treatment or prevention of inflammatory, autoimmune, allergic, and ocular diseases.

Synthesis of 2,3-dichloroquinoxalines via vilsmeier reagent chlorination

A convenient and high-yielding synthesis of 2,3-dichloroquinoxalines from the corresponding 2,3- dihydroxyquinoxalines has been developed. Treatment of a slurry of the 2,3-dihydroxyquinoxaline 1a-j with N,N-dimethylformamide in the presence of excess thionylchloride in 1,2-dichloroethane results in the rapid and high-yielding formation of the 2,3-dichloroquinoxaline derivatives 2a-j. Simplified workup and purification procedures for these compounds are also described.

Synthesis and Fungicidal Activity of 1,4-Dithiino[2,3-b]quinoxaline-2,3-dicarbonitriles

A series of eleven 1,4-dithiino[2,3-b]quinoxaline-2,3-dicarbonitriles was prepared by reaction of 2,3-dichloroquinoxalines with disodium (Z)-2,3-dimercapto-2-butenedinitrile in N,N-dimethylformamide. These products were tested for in-vitro fungicidal activity by a Minimum Inhibitory Concentration (MIC) method. Several of these compounds showed broad-spectrum fungicidal activity. The activity exhibited by these compounds was greatly dependent upon the substituents of the quinoxaline ring, with the nitro-substituted derivatives showing the higest levels of antifungal activity. None of the compounds prepared, however, showed fungicidal activity comparable to that of the commercial fungicides screened.