6954-91-2

Basic information

• Product Name: 11H-INDENO[1,2-B]QUINOXALIN-11-ONE
• Synonyms: 11H-INDENO[1,2-B]QUINOXALIN-11-ONE;indeno[1,2-b]quinoxalin-11-one
• CAS NO: 6954-91-2
• Molecular Formula: C₁₅H₈N₂O
• Molecular Weight: 232.24
• Mol File: 6954-91-2.mol
• Article Data: 59

Chemical Properties

• Boiling Point: 450.9°C at 760 mmHg
• Flash Point: 226.2°C
• Appearance: /
• Density: 1.404g/cm³
• Vapor Pressure: 2.55E-08mmHg at 25°C
• Refractive Index: 1.758
• CAS DataBase Reference: 11H-INDENO[1,2-B]QUINOXALIN-11-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 11H-INDENO[1,2-B]QUINOXALIN-11-ONE(6954-91-2)
• EPA Substance Registry System: 11H-INDENO[1,2-B]QUINOXALIN-11-ONE(6954-91-2)

Safety Data

• Hazardous Substances Data: 6954-91-2(Hazardous Substances Data)

Usage

General Description

11H-Indeno[1,2-b]quinoxalin-11-one is a polycyclic aromatic compound with the molecular formula C15H8N2O. It is a heterocyclic organic compound that consists of a quinoxaline ring fused with a benzene ring. This chemical is used in various fields such as medicinal chemistry, organic synthesis, and materials science. It exhibits interesting biological activities, including anti-inflammatory and anti-cancer properties. Additionally, it has been studied for its potential as a fluorescent probe in bioimaging and as a ligand for coordination chemistry. The compound's unique structure and diverse properties make it a valuable and versatile molecule in chemical research and development.

InChI:InChI=1/C15H8N2O/c18-15-10-6-2-1-5-9(10)13-14(15)17-12-8-4-3-7-11(12)16-13/h1-8H

Upstream product

• 485-47-2 indan-1,2,3-trione hydrate 
• 95-54-5 1,2-diamino-benzene 
• 3885-46-9 ethyl 3-(phenyl)quinoxaline-2-carboxylate 
• 53256-22-7 ethyl β-anilinocinnamate 
• 92427-66-2 3-phenylquinoxaline-2-carboxylic acid 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 62-53-3 aniline 
• 91-56-5 indole-2,3-dione 
• 452-58-4 2,3-Diaminopyridine 
• 1427070-18-5 benzo[a]phenazine-5,6-dione 7-oxide 
• 938-24-9 indantrione 
• 106-49-0 p-toluidine 
• 615-13-4 2-indanone 
• 225-61-6 1,2-benzophenazine 

Downstream Products

• 32849-88-0 indeno[1,2-b]quinoxalin-11-ylidene-p-tolyl-amine 

Relevant articles and documents

Domino multicomponent approach for the synthesis of functionalized spiro-indeno[1,2-b]quinoxaline heterocyclic hybrids and their antimicrobial activity, synergistic effect and molecular docking simulation

An expedient synthesis of hitherto unexplored novel hybrid heterocycles comprising dispiropyrrolidine, N-styrylpiperidone and indeno[1,2-b]quinoxaline units has been developed via domino multicomponent 1,3-dipolar cycloaddition strategy employing a new cl

Synthesis of new spiro compounds proceeding from 11H-Indeno[1,2-b]quinoxalin-2-one

Reaction of 11H-indeno[1,2-b]quinoxalin-2-one with semi(thiosemi)carbazides in ethanol resulted in semi(thiosemi)carbazones which at boiling in acetic anhydride underwent cylization yielding N-{3′-acetyl-3′H-spiro[indeno[1,2-b]quinoxalin-11,2′-[1,3,4]oxa(

One-pot three-component synthesis of novel spiroindenoquinoxalines

Numerous new spiroindenoquinoxalines containing pyrano groups were synthesized via a one-pot, three-component reaction of indenoquinoxaline, malononitrile with various α-methylenecarbonyl compounds (β-diketones, pyrazolones) catalyzed by triethylamine.

Synthesis of new functionally substituted hetarylcarbamates from methyl {4-[(2E)-3-(4-methoxyphenyl)-prop-2-enoyl]phenyl}carbamate

Three-component condensation of methyl {4-[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]phenyl}- carbamate with ninhydrin and L-proline in methanol–water (10: 1) afforded methyl {4-[1,3-dioxo-1′- (4-methoxyphenyl)-1,1′,2′,3,5′,6′,7′,7a′-octahydrospiro[indene-2,3′

A synthesis of spirofuran-indenoquinoxalines via isocyanid-based one-pot four-component reaction

A simple and versatile procedure for the combinatorial synthesis of (Z)-dialkyl-5-(alkylimino)-5H-spiro[furan-2,11′-indeno[1,2-b]quinoxaline]-3,4-dicarboxylates via the catalyst-free one-pot four-component reaction of ninhydrin, benzene-1,2-diamines, dial

Dispiropyrrolidinyl-piperidone embedded indeno[1,2-b]quinoxaline heterocyclic hybrids: Synthesis, cholinesterase inhibitory activity and their molecular docking simulation

A small library of new class of dispiropyrrolidinyl-piperidone tethered indono[1,2-b]quinoxaline heterocyclic hybrids 7a–j were synthesized employing multicomponent 1,3-dipolar cycloaddition strategy in [bmim]Br. The azomethine ylide employed is first of

Domino synthesis of quinoxaline derivatives using SBA-Pr-NH2 as a nanoreactor and their spectrophotometric complexation studies with some metals ions

Abstract: Amino-functionalized SBA-15 (SBA-Pr-NH2) with a pore size of 6?nm has been used as a basic nanocatalyst in the domino one-pot synthesis of quinoxaline derivatives via the four-component reaction of ninhydrin, 1,2-aryl-diamines, malono derivatives, and α-methylenecarbonyl compound using microwave irradiation. The solid basic catalyst plays a significant role in catalysis, and enhancing the rate and yield of the reaction, it can be easily handled and removed from the reaction mixture by simple filtration and also reused several times without substantial loss of reactivity. Moreover, the complexation reaction between quinoxaline as a model ligand and some metal ions including Cd2+, Co2+, Cu2+, Fe3+, Hg2+, Ni2+, Pb2+, and Zn2+ ions was examined spectrophotometrically in DMF solution at 25?°C. The formation constants of the resulting complexes were calculated from the computer fitting of the molar absorbance measurements in different mole ratios. The obtained data indicated that the stability constant of the resulting complexes varied in the following order Pb2+>?Hg2+>?Cd2+>?Ni2+>?Cu2+>?Fe3+>?Zn2+>?Co2+.

TiO2-mediated, one-pot, four-component 1,3-dipolar cycloaddition reaction: A facile synthesis of dispiro-pyrrolidine ring systems

An expedient regioselective synthesis of dispiroindenoquinoxaline pyrrolidine derivatives mediated by TiO2 in a one-pot, four-component 1,3-dipolar cycloaddition reaction is described. Copyright Taylor & Francis Group, LLC.

DNA interaction, anticancer, antibacterial, ROS and lipid peroxidation studies of quinoxaline based organometallic Re(I) carbonyls

Hetero mononuclear rhenium(I) complexes (I-V) using ligands (L1-L5) [L1-L5 = 11-((2-chlorobenzylidene)hydrazono)-11H-indeno[1,2-b]quinoxaline (L1), 8-methyl-11-((4-methyl-benzylidene)hydrazono)-11H-indeno[1,2-b]quinoxaline (L2), 11-((4-bromobenzylidene) hydrazono)-8-nitro-11H-indeno[1,2-b]quinoxaline (L3), 11-((4-bromobenzylidene) hydrazono)-8-chloro-11H-indeno[1,2-b]quinoxaline (L4), 8-bromo-11-((4-fluorobenzylidene) hydrazono)-11H-indeno[1,2-b]quinoxaline (L5)] were synthesized and characterized by spectroscopic method. All the synthesized compounds have biological importance. DNA interaction studies gave information about the modes of binding and the nucleolytic efficiency of compounds. The binding of the rhenium complexes to Herring sperm DNA (HS DNA) was monitored by UV–visible spectroscopy, viscosity measurements, and molecular docking studies; groove binding was suggested as the most possible mode. The DNA-complexes binding strength was measured in terms of intrinsic binding constants. In vivo and In vitro cytotoxicity against the eukaryotic and prokaryotic cells gave the toxic nature of the synthesized compounds. An antimicrobial study was carried out by estimating MIC (Minimum Inhibitory Concentration) against two Gram-positive (S. aureus, B. subtilis) and three Gram-negative (S. marcescens, P. aeruginosa, E. coli) bacteria. All synthesized complexes are biologically more active than the corresponding ligands. Complexes were having higher MDA and H2O2 production than ligands.

Activities of quinoxaline, nitroquinoxaline, and [1,2,4]triazolo [4,3-a]quinoxaline analogs of mmv007204 against schistosoma mansoni

The reliance on one drug, praziquantel, to treat the parasitic disease schistosomiasis in millions of people a year shows the need to further develop a pipeline of new drugs to treat this disease. Recently, an antimalarial quinoxaline derivative (MMV007204) from the Medicines for Malaria Venture (MMV) Malaria Box demonstrated promise against Schistosoma mansoni. In this study, 47 synthesized compounds containing quinoxaline moieties were first assayed against the larval stage of this parasite, newly transformed schistosomula (NTS); of these, 16 killed over 70% NTS at 10mM. Further testing against NTS and adult S. mansoni yielded three compounds with 50% inhibitory concentrations (IC50s) of#0.31mM against adult S. mansoni and selectivity indices of$8.9. Administration of these compounds as a single oral dose of 400mg/kg of body weight to S. mansoni-infected mice yielded only moderate worm burden reduction (WBR) (9.3% to 46.3%). The discrepancy between these compounds' good in vitro activities and their poor in vivo activities indicates that optimization of their pharmacokinetic properties may yield compounds with greater bioavailabilities and better antischistosomiasis activities in vivo.