49568-78-7

Usage

Uses

Used in Pharmaceutical Industry:
2-Benzyl-3-chloroquinoxaline is used as a pharmaceutical compound for its potential antifungal, antibacterial, and antimalarial properties. Its promising biological activities have made it an interesting target for the development of new drugs to combat various infections and diseases.
Used in Chemical Research:
In the field of chemical research, 2-benzyl-3-chloroquinoxaline serves as a valuable quinoxaline derivative for studying its chemical properties and potential applications in the synthesis of other related compounds with therapeutic or industrial uses.

InChI:InChI=1/C15H11ClN2/c16-15-14(10-11-6-2-1-3-7-11)17-12-8-4-5-9-13(12)18-15/h1-9H,10H2

Upstream product

• 24949-43-7 3-benzylquinoxalin-2-one 
• 95-54-5 1,2-diamino-benzene 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 881-90-3 4-benzylidene-2-methyl-2-oxazolin-5-one 
• 2213-63-0 2,3-dichloroquinoxaline 
• 6921-34-2 benzylmagnesium chloride 
• 24949-43-7 3-benzylquinoxalin-2-ol 

Downstream Products

• 223929-23-5 (3-benzyl-quinoxalin-2-yl)-hydrazine 
• 261729-55-9 4-benzyl-1-methyl-1,2,4-triazolo[4,3-a]quinoxaline 
• 1252995-51-9 4-benzyl-1-(2-chlorophenyl)-[1,2,4]triazolo[4,3-a]quinoxaline 
• 1252995-53-1 4-benzyl-[1,2,4]triazolo[4,3-a]quinoxaline 
• 261729-53-7 1-ethoxycarbonyl-4-benzyl-1,2,4-triazolo[4,3-a]quinoxaline 

Relevant academic research and scientific papers

Halting colorectal cancer metastasis via novel dual nanomolar MMP-9/MAO-A quinoxaline-based inhibitors; design, synthesis, and evaluation

Matrix metalloproteinase-9 (MMP-9) and monoamine oxidase-A (MAO-A) are central signaling nodes in CRC and promotors of distant metastasis associated with high mortality rates. Novel series of quinoxaline-based dual MMP-9/MAO-A inhibitors were synthesized

Core-Modified Coelenterazine Luciferin Analogues: Synthesis and Chemiluminescence Properties

In this work on the design and studies of luciferins related to the blue-hued coelenterazine, the synthesis of heterocyclic analogues susceptible to produce a photon, possibly at a different wavelength, is undertaken. Here, the synthesis of O-acetylated derivatives of imidazo[1,2-b]pyridazin-3(5 H)-one, imidazo[2,1-f][1,2,4]triazin-7(1 H)-one, imidazo[1,2-a]pyridin-3-ol, imidazo[1,2-a]quinoxalin-1(5 H)-one, benzo[f]imidazo[1,2-a]quinoxalin-3(11 H)-one, imidazo[1′,2′:1,6]pyrazino[2,3-c]quinolin-3(11 H)-one, and 5,11-dihydro-3 H-chromeno[4,3-e]imidazo[1,2-a]pyrazin-3-one is described thanks to extensive use of the Buchwald–Hartwig N-arylation reaction. The acidic hydrolysis of these derivatives then gave solutions of the corresponding luciferin analogues, which were studied. Not too unexpectedly, even if these were “dressed” with substituents found in actual substrates of the nanoKAZ/NanoLuc luciferase, no bioluminescence was observed with these compounds. However, in a phosphate buffer, all produced a light signal, by chemiluminescence, with extensive variations in their respective intensity and this could be increased by adding a quaternary ammonium salt in the buffer. This aspect was actually instrumental to determine the emission spectra of many of these luciferin analogues.

Design, synthesis and biological evaluation of novel 1,2,4-triazolo and 1,2,4-triazino[4,3-a]quinoxalines as potential anticancer and antimicrobial agents

In an effort to find new leads as anticancer or antimicrobial agents, the present work deals with the synthesis of some novel 1-substituted 1,2,4-triazolo[4,3-a]quinoxalines 7, 9a,b, and 14-19 and 1,2,4-triazino[4,3-a]quinoxalines 10a-c as well as 2-[5-amino-3-(4-chlorophenyl)pyrazol-1-yl]-3-benzylquinoxaline 13. These were synthesized using the key intermediate 3-benzyl-2-hydrazinoquinoxaline 6 with various reagents. Ten compounds, namely 7, 9a, 10b, 11, and 13-18 were chosen by the National Cancer Institute of Bethesda (NCI) for evaluation of their anticancer activity. The results indicated that 9a was the most active and was further evaluated for in vitro five dose assay against 60 human cell lines. It was proven to possess the highest broad spectrum anticancer activity. It showed particular effectiveness towards leukemia SR, non-small cell lung cancer HOP-92, NCI-H460, colon cancer HCT-116, HCT-15, CNS cancer U251, melanoma LOX IMVI, renal cancer A498, prostate cancer PC-3, and breast cancer MDA-MB-468 cell lines (GI50 = 3.91, 3.45, 3.49, 3.21, 1.96, 5.18, 3.69, 1.80, 5.19, and 5.55 μM, respectively). All new compounds were screened for their antimicrobial activity and were very active against P. aeruginosa. Compounds 10a and 16 were twice as active as ampicillin against P. aeruginosa. Five compounds, 9a, b, 10b, 13, and 14 were equipotent to ampicillin against P. aeruginosa. In addition, compound 16 showed a broad spectrum antimicrobial activity. Furthermore, compound 9a showed dual activity as an anticancer and antimicrobial agent. This journal is

Exploring new selective 3-benzylquinoxaline-based MAO-A inhibitors: Design, synthesis, biological evaluation and docking studies

In this investigation, we searched for novel MAO-A inhibitors using a 3-benzylquinoxaline scaffold based on our earlier findings. Series of N′-(3-benzylquinoxalin-2-yl)acetohydrazide, 4a, N′-(3-benzylquinoxalin-2-yl)benzohydrazide derivatives 4b-f, N′-[2-

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.

Synthesis of 3-benzyl-2-substituted quinoxalines as novel monoamine oxidase A inhibitors

A new series of 3-benzyl-2-substituted quinoxalines have been synthesized by means of microwave enhancement of nucleophilic substitution reaction involving the corresponding 2-chloroquinoxaline analogs and substituted amines or hydrazine. The synthesized

Quinoxaline compounds and methods of using them

The present invention generally relates to quinoxaline compounds having Formula 1 or Formula 2 wherein the variables are as defined herein, and methods of using them.

Fused pyrazine compounds

The compound of the formula (I): wherein all the symbols are meaning the same as descriptions of the specification; and salts thereof. The compounds of the formula (I) have inhibitory activity of adhesion molecules expression, and are useful for prevention and/or treatment of inflammation, rheumatoid arthritis, allergies, asthma, atopic dermatitis, psoriasis, suppression of ischemia reperfusion injury, nephritis, hepatitis, multiple sclerosis, ulcerative colitis, adult respiratory distress syndrome (ARDS), suppression of transplant rejection, sepsis, diabetes, autoimmune diseases, tumor metastasis, arteriosclerosis and AIDS.