33707-91-4

Usage

Chemical Properties

White solid

InChI:InChI=1/C14H10N2O/c17-11-7-5-10(6-8-11)14-9-15-12-3-1-2-4-13(12)16-14/h1-9,17H

Upstream product

• 24645-80-5 (4-hydroxylphenyl)glyoxal 
• 95-54-5 1,2-diamino-benzene 
• 99-93-4 4-Hydroxyacetophenone 
• 51-67-2 tyrosamine 
• 99233-31-5 1-(4-hydroxyphenyl)-2-iodoethanone 
• 2491-38-5 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone 

Downstream Products

• 312272-69-8 acetic acid-(4-quinoxalin-2-yl-phenyl ester) 
• 305858-17-7 benzoic acid-(4-quinoxalin-2-yl-phenyl ester) 
• 5021-46-5 2-(4-methoxyphenyl)quinoxaline 
• 1265637-53-3 3-(4-Methoxy-benzyl)-5-(4-quinoxalin-2-yl-phenoxy)-3,4-dihydro-1H-pyrido[2,3-d]pyrimidin-2-one 
• 1262801-89-7 3-nitro-4-(quinoxalin-2-yl)phenol 

Relevant academic research and scientific papers

Copper-catalyzed aerobic oxidative coupling of o-phenylenediamines with 2-aryl/heteroarylethylamines: direct access to construct quinoxalines

A copper-catalyzed oxidative coupling reaction of o-phenylenediamines with 2-aryl/heteroarylethylamines using molecular oxygen as an oxidant has been developed. This approach provides a practical and direct access to construct quinoxalines in excellent yields at room temperature. The reaction has a broad substrate scope and exhibits excellent functional-group tolerance. This method could be easily scaled up and applied to the synthesis of biologically active molecules bearing a quinoxaline structural scaffold.

Quinoxaline derivatives: Novel and selective butyrylcholinesterase inhibitors

Alzheimer's disease (AD) is a progressive brain disorder which occurs due to lower levels of acetylcholine (ACh) neurotransmitters, and results in a gradual decline in memory and other cognitive processes. Acetycholinesterase (AChE) and butyrylcholinesterase (BChE) are considered to be primary regulators of the ACh levels in the brain. Evidence shows that AChE activity decreases in AD, while activity of BChE does not change or even elevate in advanced AD, which suggests a key involvement of BChE in ACh hydrolysis during AD symptoms. Therefore, inhibiting the activity of BChE may be an effective way to control AD associated disorders. In this regard, a series of quinoxaline derivatives 1-17 was synthesized and biologically evaluated against cholinesterases (AChE and BChE) and as well as against achymotrypsin and urease. The compounds 1-17 were found to be selective inhibitors for BChE, as no activity was found against other enzymes. Among the series, compounds 6 (IC50 = 7.7 ± 1.0μM) and 7 (IC50 = 9.7 ± 0.9 μM) were found to be the most active inhibitors against BChE. Their IC50 values are comparable to the standard, galantamine (IC50 = 6.6 ± 0.38 μM). Their considerable BChE inhibitory activity makes them selective candidates for the development of BChE inhibitors. Structure-activity relationship (SAR) of this new class of selective BChE inhibitors has been discussed.

Logic design and synthesis of quinoxalines via the integration of iodination/oxidation/cyclization sequences from ketones and 1,2-diamines

A novel protocol for the synthesis of quinoxalines has been developed from simple ketones and 1,2-diamines. This process underwent a logic approach to bis-substituted quinoxalines via a consecutive iodination/Kornblum oxidation/cyclization in the presence of I2/CuO/DMSO and to mono-substituted quinoxalines via an iodination/cyclization/aromatization in the presence of I2/CuO/K3PO4·3H 2O.

A mild and convenient synthesis of quinoxalines via cyclization-oxidation process using DABCO as catalyst

An efficient and general method has been described for the synthesis of quinoxalines by the reaction of 1,2-diamines with phenacyl bromides in the presence of DABCO. The method is suitable for the preparation of functionalized quinoxalines.