2942-02-1

Basic information

• Product Name: 2-Methyl-6-nitroquinoxaline
• CAS NO: 2942-02-1
• Molecular Formula: C₉H₇N₃O₂
• Molecular Weight: 189.17078
• EINECS: -0
• Mol File: 2942-02-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Methyl-6-nitroquinoxaline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-6-nitroquinoxaline(2942-02-1)
• EPA Substance Registry System: 2-Methyl-6-nitroquinoxaline(2942-02-1)

Safety Data

• Hazardous Substances Data: 2942-02-1(Hazardous Substances Data)

Upstream product

• 102-69-2 tri-n-propylamine 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 131543-46-9 Glyoxal 
• 78-98-8 2-oxopropanal 

Downstream Products

• 4188-17-4 2-methyl-6-amino-quinoxaline 
• 78411-56-0 2-amino-3,7-dimethylimidazo<4,5-f>quinoxaline 

Relevant articles and documents

6- endo -dig Cycloisomerization of N -Propargyl Aminoquinoxalines: A New Route to 1,4,8-Triazaphenanthrenes

We report the preparation of novel 1,4,8-triazaphenanthrenes and show that the target compounds are efficiently obtained from the corresponding 6-aminoquinoxalines after N-propargylation followed by copper-catalyzed 6-endo-dig cycloisomerization and aroma

Method for synthesizing quinoxaline compound under visible light induced iron catalysis condition

The invention belongs to the technical field of compound synthesis, and particularly relates to a method for synthesizing quinoxaline compounds under visible light induced iron catalysis conditions. The method comprises the following steps: by taking non-activated aliphatic amine and o-phenylenediamine as raw materials, under the action of a photosensitizer, under the illumination of visible light, reacting in a solvent at room temperature and under oxygen conditions to generate the quinoxaline compound. The method has better substrate universality and relatively mild reaction conditions, not only realizes synthesis of the quinoxaline compound for the first time, but also widens the field of organic synthesis.

Luminescent ruthenium polypyridyl complexes with extended 'dppz' like ligands as DNA targeting binders and cellular agents

Four new Ru(ii) polypyridyl complexes that contain an extended aromatic moiety derived from pyrazino[2,3-h]dipyrido[3,2-a:2′,3′-c]phenazine and either 1,10-phenanthroline (phen) or 1,4,5,8-tetraazaphenanthrene (TAP) have been synthesized, their solid state X-ray crystal structure determined and their photophysical and biological properties evaluated. Their interactions with DNA have been studied, and they have been tested for their potential as photodynamic therapeutic (PDT) agents in the treatment of cancer. A practical modification of a method by Carter, Rodriguez and Bard has been introduced and used to calculate binding parameters for the complexes which show a strong affinity for DNA with binding constants in the order of 107 M1 (in 10 mM phosphate buffer). The complexes containing phen as an ancillary ligand become emissive upon binding to DNA (“light switch effect”), but do not show selective cytotoxicity upon light irradiation. On the other hand, the TAP complexes, which show an inverse “light switch effect” (emission quenched upon binding to DNA), are strongly photo-toxic suggesting their use in Photodynamic Therapy (PDT). In HeLa cells the best PDT agent shows an IC50 value (light) = 4 μM vs. IC50 value (dark) = 62 μM.

New 6-Aminoquinoxaline Derivatives with Neuroprotective Effect on Dopaminergic Neurons in Cellular and Animal Parkinson Disease Models

Parkinson's disease (PD) is a neurodegenerative disorder of aging characterized by motor symptoms that result from the loss of midbrain dopamine neurons and the disruption of dopamine-mediated neurotransmission. There is currently no curative treatment for this disorder. To discover druggable neuroprotective compounds for dopamine neurons, we have designed and synthesized a second-generation of quinoxaline-derived molecules based on structure-activity relationship studies, which led previously to the discovery of our first neuroprotective brain penetrant hit compound MPAQ (5c). Neuroprotection assessment in PD cellular models of our newly synthesized quinoxaline-derived compounds has led to the selection of a better hit compound, PAQ (4c). Extensive in vitro characterization of 4c showed that its neuroprotective action is partially attributable to the activation of reticulum endoplasmic ryanodine receptor channels. Most interestingly, 4c was able to attenuate neurodegeneration in a mouse model of PD, making this compound an interesting drug candidate for the treatment of this disorder.

HETEROCYCLIC DERIVATIVES THAT ARE USED IN THE TREATMENT OF NEURODEGENERATIVE DISEASES

The present invention relates to compounds of Formula (I) below, to their pharmaceutically acceptable salts and to their isomers or mixtures of isomers: HetAr—X—CHR1R2 (I) in which: -HetAr represents a group chosen from: —X represents a linear, saturated or unsaturated, hydrocarbon-based chain comprising from 8 to 22 carbon atoms, optionally interrupted by an —NH— or —NH—CO— group, —R1 represents a hydrogen atom or an —OH, —O(C1-C6)alkyl, —OCO((C1-C6)alkyl), —OSO2((C1-C6)alkyl) or —OSO3H group, and —R2 represents a hydrogen atom or a (C2-C6)alkynyl, (C2-C6)alkenyl or (C3-C6)cycloalkyl group. The present invention also relates to a process for preparing the compounds of Formula (I), and also to the use thereof, especially in the treatment of neurodegenerative diseases.

Bicyclic aromatic substituted pyridone derivative

Disclosed is a compound represented by the formula (I): Wherein R1 and R2 independently represent a hydrogen atom, a lower alkyl group or the like; X1, X2 and X3 independently represent a methine group or a nitrogen atom; Y1 and Y3 independently represent a single bond, —O— or the like; Y2 represents a lower alkylene group or the like; W1 to W4 independently represent a single bond, a methylene group or the like; L represents a single bond, a methylene group or the like; Z1 and Z2 independently represent a single bond, a C1-4 alkylene group or the like; Ar1 represents an aromatic carbocyclic ring or the like; and Ar2 represents a bicyclic aromatic carbocyclic ring or the like. The compound is useful as a pharmaceutical for a central disease, a cardiovascular disease or a metabolic disease.

Novel highly regioselective syntheses of unsymmetrical 2,3-disubstituted quinoxalines

Non-symmetrical 2,3-disubstituted quinoxalines are not easily obtained in good yields because of the lack of regioselectivity of the Hinsberg condensation, or the large number of steps required for achieving their preparation. Two efficient methods leadin

BICYCLIC AROMATIC SUBSTITUTED PYRIDONE DERIVATIVE

Disclosed is a compound represented by the formula (I): wherein R1 and R2 independently represent a hydrogen atom, a lower alkyl group or the like; X1, X2 and X3 independently represent a methine group or a nitrogen atom; Y1 and Y3 independently represent a single bond, -O- or the like; Y2 represents a lower alkylene group or the like; W1 to W4 independently represent a single bond, a methlene group or the like; L represents a single bond, a methylene group or the like; Z1 and Z2 independently represent a single bond, a C1-4 alkylene group or the like; Ar1 represents an aromatic carbocyclic ring or the like; and Ar2 represents a bicyclic aromatic carbocyclic ring or the like. The compound is useful as a pharmaceutical for a central disease, a cardiovascular disease or a metabolic disease.

Synthesis and antiprotozoal activity of some new synthetic substituted quinoxalines

A series of 29 new quinoxalines was synthesized and evaluated in vitro against several parasites (Leishmania donovani, Trypanosoma brucei brucei, and Trichomonas vaginalis). Several of them displayed interesting activities, and particularly four quinoxaline amides showed in vitro antileishmanial properties (IC50 less than 20 μM).

FIBROSIS INHIBITOR

Medicament being useful as a fibrosis inhibitor for organs or tissues, which comprises a compound of the formula (I): wherein Ring Z is optionally substituted pyrrole ring, etc.; W2 is -CO-, -SO2-, optionally substituted C1-C4 alkylene, etc.; Ar2 is optionally substituted aryl, etc.; W1 and Ar1 mean the following (1) and (2):(1) W1 is optionally substituted C1-C4 alkylene, etc.; Ar1 is optionally substituted bicyclic heteroaryl having 1 to 4 nitrogen atoms as ring-forming atoms:(2) W1 is optionally substituted C2-C5 alkylene, optionally substituted C2-C5 alkenylene, etc.; and Ar1 is aryl or monocyclic heteroaryl, which is substituted by carboxyl, alkoxycarbonyl, etc. at the ortho- or meta-position thereof with respect to the binding position of W1, or a pharmaceutically acceptable salt thereof.