75163-14-3

Usage

Properties

1. Chemical formula: C18H24N4
2. Heterocyclic organic compound
3. Consists of a quinoxaline ring substituted with two piperidine rings
4. Commonly used in the pharmaceutical industry
5. Potential use as a ligand in coordination chemistry
6. Used as a precursor in the production of complex organic compounds
7. Being researched for potential pharmacological properties
8. Investigated for therapeutic applications in the treatment of medical conditions

Specific content

1. Molecular formula: C18H24N4
2. Consists of a quinoxaline ring with two piperidine rings
3. Used as a building block for the synthesis of bioactive molecules and drugs
4. Potential use as a ligand in coordination chemistry
5. Precursor in the production of other complex organic compounds
6. Researching for potential pharmacological properties
7. Investigating therapeutic applications in the treatment of medical conditions.

Upstream product

• 110-89-4 piperidine 
• 2213-63-0 2,3-dichloroquinoxaline 
• 75163-15-4 2-chloro-3-(phenylethynyl)quinoxaline 
• 87885-47-0 2-chloro-3-nitroquinoxaline 

Relevant academic research and scientific papers

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.

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.

Alkynyl- and Dialkynyl-quinoxalines. Synthesis of Condensed Quinoxalines

Condensation of 2-chloro- and 2,3-dichloroquinoxalines with alk-1-ynes in the presence of bis(triphenylphosphine)palladium(II) dichloride and copper(I) iodide gives mono- and di-alkynylquinoxalines.Addition of amines to these products gives stable enamines; hydration gives 2'-oxoalkyl compounds which exist predominantly in the intramolecularly hydrogen-bonded enol form.Condensation of the alkynylquinoxalines with diethyl sodiomalonate, and related compounds, yields pyridoquinoxalin-4-one derivatives. 2-Alkynyl-3-chloroquinoxalines are intermediates for convenient syntheses of pyrroloquinoxalines.