58773-29-8

Usage

Structure

Thione derivative of quinoxaline with a methyl group attached to the 3rd position

Heterocyclic compound

Contains two nitrogen atoms and a sulfur atom in its ring structure

Usage

Pharmaceutical and agricultural applications

Medicinal properties

Antimicrobial and antifungal activities

Potential

Promising candidate for drug development

Pesticidal properties

Useful for controlling pests and diseases in agricultural settings.

Upstream product

• 32601-86-8 2-chloro-3-methylquinoxaline 
• 17356-08-0 thiourea 
• 14003-34-0 3-methyl-2-oxo-1,2-dihydroquinoxaline 
• 95-54-5 1,2-diamino-benzene 
• 14003-34-0 3-methylquinoxalin-2-ol 

Downstream Products

• 141804-49-1 2-phenyl-2-(3-methylquinoxalin-2-yl)ethanethiol 
• 84546-81-6 2-(benzylthio)-3-methylquinoxaline 
• 84546-82-7 2-(p-nitrobenzylthio)-3-methylquinoxaline 
• 95155-68-3 2-(3-methylquinoxalin-2-yl)cyclohexane-1-thiol 

Relevant academic research and scientific papers

Discovery of new quinoxaline-based derivatives as anticancer agents and potent VEGFR-2 inhibitors: Design, synthesis, and in silico study

VEGFR-2 is one of the most vital targets for the treatment of solid tumors. This work represents synthetic approaches of new set of quinoxaline-based derivatives having comparable essential pharmacophoric properties of VEGFR-2 inhibitors. The antiproliferative findings revealed that compound 21a displayed the most potent effect against MCF-7 and HepG2 cell lines with IC50 values of 12.9 and 7.5 μM, respectively. Further assessment was carried out for all the synthesized members against VEGFR-2 enzyme. Excitingly, the data of VEGFR-2 assay were comparable to that of antiproliferative assay. Compound 21a was the most powerful member against VEGFR-2 with an IC50 value of 3.8 nM, comparing to sorafenib (IC50 = 3.12 nM). Finally, molecular docking experiments were conducted to foresee how the synthesized compounds can bind to their prospective biological target; VEGFR-2. The docking results showed the ability of the synthesized compounds to bind VEGFR-2 in a correct manner. Lastly, computational physicochemical estimation of the most active candidates displayed that they have favorable assets with reasonable drug-likeness reports.

New quinoxaline-based VEGFR-2 inhibitors: Design, synthesis, and antiproliferative evaluation with: In silico docking, ADMET, toxicity, and DFT studies

A new series of 3-methylquinoxaline-based derivatives having the same essential pharmacophoric features as VEGFR-2 inhibitors have been synthesized and evaluated for their antiproliferative activities against two human cancer cell lines, MCF-7 and HepG-2. Compounds 15b and 17b demonstrated a significant antiproliferative effect with IC50 ranging from 2.3 to 5.8 μM. An enzymatic assay was carried out for all the tested candidates against VEGFR-2. Compound 17b was the most potent VEGFR-2 inhibitor (IC50 = 2.7 nM). Mechanistic investigation including cell cycle arrest and apoptosis was performed for compound 17b against HepG-2 cells, and the results revealed that 17b induced cell apoptosis and arrested cell cycle in the G2/M phase. Moreover, apoptosis analyses were conducted for compound 17b to evaluate its apoptotic potential. The results showed upregulation in caspase-3 and caspase-9 levels, and improving the Bax/Bcl-2 ratio by more than 10-fold. Docking studies were performed to determine the possible interaction with the VEGFR-2 active site. Further docking studies were carried out for compound 17b against cytochrome P450 to present such compounds as non-inhibitors. In silico ADMET, toxicity, and physico-chemical properties revealed that most of the synthesized members have acceptable values of drug-likeness. Finally, DFT studies were carried out to calculate the thermodynamic, molecular orbital and electrostatic potential properties.

A novel method for heterocyclic amide-thioamide transformations

In this paper, we introduce a novel and convenient method for the transformation of heterocyclic amides into heteocyclic thioamides. A two-step approach was applied for this transformation: Firstly, we applied a chlorination of the heterocyclic amides to afford the corresponding chloroheterocycles. Secondly, the chloroherocycles and N-cyclohexyl dithiocarbamate cyclohexylammonium salt were heated in chloroform for 12 h at 61°C to afford heteocyclic thioamides in excellent yields.

Synthesis and Biological Evaluation of 2-Oxo/Thioxoquinoxaline and 2-Oxo/Thioxoquinoxaline-Based Nucleoside Analogues

Several O-and S-quinoxaline glycosides have been prepared by glycosidation of 3-methyl-2-oxo(thioxo)-1,2-dihydroquinoxalines 1a,b with α-D-glucopyranosyl, α-D-galactopyranosyl, and α-D-lactosyl bromide in the presence of K2CO3 followed by deacetylation with Et3N/H2O. Furthermore, alkylation of 1a,b with 4-bromobutyl acetate, 2-acetoxyethoxymethyl bromide, and 3-chloropropanol afforded the corresponding O-and S-acycloquinoxaline nucleosides. Reaction of 1b with chloroacetic acid followed by condensation with sulfacetamide and sulfadiazine in the presence of Et3N/THF and ethyl chloroformate gave the corresponding sulfonamide derivatives 14 and 15, respectively. The structures of new compounds were confirmed by using IR, 1H, 13C NMR spectra and microanalysis. Some of these compounds were screened in vitro for antitumor and antifungal activities.

Cyclisation reaction between 3-methylquinoxaline-2-thione and benzaldehydes into 3-benzyl-2-aryl-thieno[2,3-b] quinoxaline promoted by Br?nsted acids

2,3-Disubstituted thieno[2,3-b]quinoxaline derivatives have been synthetized through the condensation of commercially available benzaldehydes with 3-methylquinoxaline-2-thione in EtOH using Br?nsted acids, namely sulfuric or hydrochloric acids. A wide range of substituted benzaldehydes has been used, allowing the formation of 3-(substituted)benzyl-2-arylthieno[2,3-b]quinoxalines in high yields in only one step.

Synthesis and antibacterial activity of new spiro[thiadiazoline- quinoxaline] derivatives

The 1,3-dipolar cycloaddition of 3-methylquinoxaline-2-thione and their N-alkylated derivatives to diphenylnitrile imine is presented. Using this method, spiro[thiadiazoline-quinoxaline] derivatives as biologically interesting compounds were produced in h

Nematicidal quinoxaline derivatives

Compounds of formula (I) STR1 wherein R1, R2, R3, R4 and R5 are independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl, halogen, haloalkyl, alkoxy, alkenoxy, alkoxyalkyl, haloalk

Photocycloaddition of Quinoxaline-2(1H)-thiones to Alkenes

A synthetically useful C-C bond formation involving the photochemical addition of quinoxaline-2(1H)-thiones to alkenes is described.Irradiation of the quinoxaline-2(1H)-thiones 1-4 in the presence of the alkenes 7 gave the 2-(2'-mercaptoalkyl)quinoxalines 8-11 in moderate-to-good yields via ring cleavage of an intermediate aminothietane with aromatization of the quinoxaline ring.The latter was formed by photocycloaddition of the C=S bond of the quinoxaline-2(1H)-thione and the C=C bond of the alkene.