32998-25-7

Basic information

• Product Name: 2-CHLORO-3-METHOXYQUINOXALINE
• Synonyms: 2-CHLORO-3-METHOXYQUINOXALINE
• CAS NO: 32998-25-7
• Molecular Formula: C₉H₇ClN₂O
• Molecular Weight: 194.62
• Mol File: 32998-25-7.mol

Chemical Properties

• Melting Point: 71-75℃
• Boiling Point: 271℃
• Flash Point: 118℃
• Appearance: /
• Density: 1.333
• Vapor Pressure: 0.0112mmHg at 25°C
• Refractive Index: 1.628
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-CHLORO-3-METHOXYQUINOXALINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-3-METHOXYQUINOXALINE(32998-25-7)
• EPA Substance Registry System: 2-CHLORO-3-METHOXYQUINOXALINE(32998-25-7)

Safety Data

• Hazardous Substances Data: 32998-25-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-3-methoxyquinoxaline is utilized as a key building block in organic synthesis for the development of various pharmaceutical drugs and biologically active molecules. Its unique structure and properties make it a valuable component in the design and synthesis of new therapeutic agents.
Used in Antitumor Research:
2-CHLORO-3-METHOXYQUINOXALINE has been studied for its potential antitumor properties, indicating its use in the development of cancer treatments. The exploration of its antitumor activity is crucial for identifying new avenues in oncology and potentially contributing to the advancement of cancer therapies.
Used in Antimicrobial Applications:
2-Chloro-3-methoxyquinoxaline has also been examined for its antimicrobial properties, suggesting its application in the creation of antimicrobial agents to combat infections caused by various microorganisms. This research is significant for developing new antimicrobial drugs to address the growing issue of antibiotic resistance.

InChI:InChI=1/C9H7ClN2O/c1-13-9-8(10)11-6-4-2-3-5-7(6)12-9/h2-5H,1H3

Upstream product

• 2213-63-0 2,3-dichloroquinoxaline 
• 124-41-4 sodium methylate 
• 87885-47-0 2-chloro-3-nitroquinoxaline 
• 15804-19-0 quinoxaline-2,3-dione 
• 95-54-5 1,2-diamino-benzene 
• 67-56-1 methanol 
• 34117-90-3 2-amino-3-chloroquinoxaline 
• 15804-19-0 2,3-dihydroxyquinoxaline 

Downstream Products

• 35676-71-2 3-Methoxy-chinoxalin-2-on 
• 1426059-38-2 1-(3-methoxyquinoxalin-2-ylmethyl)-3-phenylurea 
• 1426058-77-6 N-(3-methoxyquinoxalin-2-ylmethyl)benzamide 
• 139389-05-2 4-chloro-1-(2-chlorophenyl)-[1,2,4]triazolo[4,3-a]quinoxaline 
• 1385829-18-4 4-{4-[2-(4-(2-methoxyquinoxalin-3-yl)piperazin-1-yl)ethyl]phenyl}thiazol-2-amine 
• 1385829-19-5 4-{4-[2-(4-(2-methoxyquinoxalin-3-yl)piperazin-1-yl)ethyl]phenyl}-N-methylthiazol-2-amine 
• 1385829-20-8 4-{4-[2-(4-(2-methoxyquinoxalin-3-yl)piperazin-1-yl)ethyl]phenyl}-5-methylthiazol-2-amine 
• 1385829-21-9 4-{4-[2-(4-(2-methoxyquinoxalin-3-yl)piperazin-1-yl)ethyl]phenyl}thiazol-2-ol 
• 1385829-22-0 C₂₆H₂₉N₅OS 
• 1385829-23-1 4-{4-[2-(4-(2-methoxyquinoxalin-3-yl)piperazin-1-yl)ethyl]phenyl}-N,5-dimethyl thiazol-2-amine 
• 1385829-24-2 2-{4-[4-(2-methylthiazol-4-yl)phenethyl]piperazin-1-yl}-3-methoxyquinoxaline 
• 1436382-86-3 2,3-diphenylfuro[3,2-b]quinoxaline 

Relevant articles and documents

Novel multi-component synthesis of 1,4-disubstituted pyrrolo[1,2-a]quinoxalines through palladium-catalyzed coupling reaction/hetero-annulation in water

1,4-Disubstituted pyrrolo[1,2-a]quinoxalines were prepared through the one-pot multi-component reactions of 3-substituted-2-chloroquinoxalines, propargyl alcohol, and secondary amines, catalyzed by Pd/Cu, in the presence of K2CO3and sodium dodecyl sulfate (SDS) in water. This process provided a facile, eco-friendly, and highly efficient method for the synthesis of new pyrrolo[1,2-a]quinoxalines in water with good yields.

Development of an unexpected reaction pathway for the synthesis of 1,2,4-trisubstituted pyrrolo[1,2-a]quinoxalines through palladium-catalyzed cascade reactions

1,2,4-trisubstituted pyrrolo[1,2-a]quinoxalines are synthesized through the multi-component reaction of 3-substituted 2-chloroquinoxalines, propargyl bromide, and excess secondary amines in the presence of a palladium copper catalytic system. This one-pot process provides an unexpected synthesis of new trisubstituted pyrrolo[1,2-a]quinoxalines by the introduction of two amine substituents onto the fused pyrrole rings in a single reaction procedure. The compounds formed are fully characterized by the analytical spectral data and X-ray analysis. A number of synthesized pyrrolo[1,2-a]quinoxaline derivatives are also screened against the three bacterial strains Micrococcus luteus, Pseudomonas aeruginos, and Bacillus subtilis. According to the results obtained, compounds 3b, 3c, and 3e are active against M.?luteus, compounds 3b and 3e are active against Ps. Aeruginos, and only compound 3f is active against all the three bacterial strains.

Efficient synthesis of 2-phenyl-3-substituted furo/thieno[2,3-: B] quinoxalines via Sonogashira coupling reaction followed by iodocyclization and subsequent palladium-catalyzed cross-coupling reactions

In this paper, we report the successful synthesis of new 2-phenyl-3-substituted furo/thieno[2,3-b]quinoxaline derivatives from 2-chloro-3-methoxyquinoxaline and 2-chloro-3-(methylthio)quinoxaline by a three-step approach. The Sonogashira coupling reaction of the title compounds with terminal alkynes afforded 2-methoxy-3-(phenylethynyl)quinoxaline and 2-(methylthio)-3-(phenylethynyl)quinoxaline in good to excellent yields. The iodocyclization of the resulting compounds using ICl in CH2Cl2 afforded 3-iodo-2-phenylfuro[2,3-b]quinoxaline and 3-iodo-2-phenylthieno[2,3-b]quinoxaline. The subsequent palladium-catalyzed Sonogashira, Suzuki, and Heck reactions of the resulting iodo compounds led to the formation of 2,3-disubstituded furo/thieno[2,3-b]quinoxaline in high yields. All compounds were fully characterized by FT-IR, mass, 1H NMR, and 13C NMR spectral data. The synthesized quinoxaline derivatives were also screened against the two bacterial strains Escherichia coli and Micrococcus luteus.

Design, synthesis, and preliminary in vitro and in vivo pharmacological evaluation of 4-{4-[2-(4-(2-substitutedquinoxalin-3-yl)piperazin-1-yl)ethyl] phenyl}thiazoles as atypical antipsychotic agents

A series of 4-{4-[2-(4-(2-substitutedquinoxalin-3-yl)piperazin-1-yl)ethyl] phenyl} thiazoles were synthesized in an effort to prepare novel atypical antipsychotic agents. The compounds were designed, synthesized, and characterized by spectral data (IR, 1H NMR, and MS) and the purity was ascertained by microanalysis. The D2 and 5-HT2A affinity of the synthesized compounds was screened in vitro by radioligand displacement assays on membrane homogenates isolated from rat striatum and rat cortex, respectively. Furthermore, all the synthesized final compounds (10a-g; 11a-g; 12a-g) were screened for their in vivo pharmacological activity in Swiss albino mice. D2 antagonism studies were performed using climbing mouse assay model and 5-HT2A antagonism studies were performed using quipazine-induced head twitches in mice. It was observed that none of the new chemical entities exhibited catalepsy and 12d, 11f, and 10a were found to be the most active compounds with 5-HT2A/D2 ratio of 1.23077, 1.14286, and 1.12857, respectively, while the standard drug risperidone exhibited 5-HT2A/D2 ratio of 1.0989. Among the twenty one new chemical entities, three compounds (12d, 11f, and 10a) were found to exhibit better atypical antipsychotic activity as they were found to have higher Meltzer index than the standard drug risperidone.

New quinoxaline derivatives as potential mt1 and mt2 receptor ligands

Ever since the idea arose that melatonin might promote sleep and resynchronize circadian rhythms, many research groups have centered their efforts on obtaining new melatonin receptor ligands whose pharmacophores include an aliphatic chain of variable length united to an N-alkylamide and a methoxy group (or a bioisostere), linked to a central ring. Substitution of the indole ring found in melatonin with a naphthalene or quinoline ring leads to compounds of similar affinity. The next step in this structural approximation is to introduce a quinoxaline ring (a bioisostere of the quinoline and naphthalene rings) as the central nucleus of future melatoninergic ligands.

AROMATIC NITROGEN-CONTAINING 6-MEMBERED RING COMPOUNDS AND THEIR USE

The present invention provides aromatic nitrogen-containing 6-membered ring compounds having execellent PDE10 inhibitory activity. The present invention relates to an aromatic nitrogen-containing 6-membered ring compound represented by the following formula [I0] or a pharmaceutically acceptable salt thereof, a method for preparing the same, and use of said compounds for PDE10 inhibitors, and a pharmaceutical composition comprising said compounds as an active ingredient: Formula [I0] wherein: X1, X2 and X3 each independently are N or CH, and at least two of X1, X2 and X3 are N; A is *-CH=CH-, *-C(Alk)=CH-, *-CH2-CH2- or *-O-CH2- (* is a bond with R1); Alk is a lower alkyl group; Ring B is an optionally substituted nitrogen-containing aliphatic heterocyclic group; R1 is an optionally substituted nitrogen-containing heterocyclic group, a nitrogen-containing heterocyclic moiety of which is a moiety selected from the group consisting of quinoxalinyl, quinolyl, isoquinolyl, quinazolinyl, pyrazinyl, pyrimidinyl and a moiety thereof fused with a 5 to 6-membered aliphatic ring thereto; Y0 is a group selected from the group consisting of the following (1) to (5): (1) an optionally substituted phenyl or an optionally substituted aromatic monocyclic 5 to 6-membered heterocyclic group; (2) an optionally substituted aminocarbonyl; (3) an optionally substituted amino lower alkyl; (4) -O-R2 wherein R2 is hydrogen, an optionally substituted lower alkyl, lower cycloalkyl, aliphatic monocyclic 5 to 6-membered heterocyclic group, or Formula [AA]; (5) mono- or di-substituted amino; provided that, when Y0 is mono- or di-substituted amino, the nitrogen-containing heterocyclic moiety of R1 is not quinoxalinyl or quinolyl.

Quinoxalinones

The invention features quinoxalinones, pharmaceutical compositions containing them and methods of using them to treat, for example, diabetes.

NUCLEOPHILIC SUBSTITUTIONS ON 2-CHLORO-3-NITROQUINOXALINE

Piperidine, cyclohexylamine, methoxide ion and para-thiocresolate ion react with 2-chloro-3-nitroquinoxaline 1 by selectively substituting the nitro group, in contrast to be behavior of most ortho-chloronitroaromatics which loose halide when subjected to nucleophilic substitution reactions.This inversion is interpreted as being due to the lack of activation of the 2-position by the nitro group in the 3-position because of the low value of the ?-bond index between these two vertices.It is also suggested that the substitution by neutral reagents such as amines is strongly influenced by stabilizing interactions between the negatively charged nitro group and the ammonium moiety in the ? complex; this built-in solvation may be responsible for inversions in the chemoselectivity between chloro and nitro nucleofugicities.