6287-20-3

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2,3-Dihydroxyquinoxaline serves as a valuable building block in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure allows it to be a key component in the development of new drugs and agricultural chemicals, enhancing their efficacy and potential applications.
Used in Antioxidant and Anticancer Research:
Due to its potential antioxidant and anticancer properties, 2,3-dihydroxyquinoxaline is being studied for its therapeutic applications. Researchers are exploring its capacity to combat oxidative stress and its possible role in inhibiting cancer cell growth, which could lead to the development of novel treatments for various types of cancer.
Safety Precautions:
It is crucial to handle 2,3-dihydroxyquinoxaline with care, as it may pose health risks if ingested, inhaled, or if it comes into contact with the skin or eyes. Appropriate safety measures should be taken to minimize the risk of irritation or harm during its use in research and industrial applications.

Upstream product

• 91-19-0 2,3-diethynylquinoxaline 
• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 21948-73-2 2-(methylthio)quinoxaline 
• 77901-51-0 (2-nitro-phenyl)-oxalamic acid 
• 144-62-7 oxalic acid 
• 95-54-5 1,2-diamino-benzene 
• 59564-59-9 1,2,3,4-tetrahydroquinoxalin-2-one 
• 471-47-6 oxamic acid 
• 59743-08-7 diethyl 2,3-dioxosuccinate 
• 95-92-1 oxalic acid diethyl ester 
• 14003-34-0 3-methyl-2-oxo-1,2-dihydroquinoxaline 
• 35676-70-1 3-chloro-quinoxaline-2(1H)-one 
• 17311-31-8 dioxidine 
• 81225-99-2 1,5-Dihydro-2H-1,5-benzodiazepin-2,3,4-trione hydrate 

Downstream Products

• 73185-66-7 3-(methylamino)quinoxalin-2(1H)-one 
• 58175-07-8 1,4-dimethylquinoxaline-2,3(1H,4H)-dione 
• 952-10-3 1,2,3,4-tetrahydro-2,3-dioxo-6-quinoxalinesulfonyl chloride 
• 88976-69-6 N-amino-1,4-dihydroquinoxaline-2,3-dione 
• 91895-51-1 4-Dimethylamino-1-ethyl[1,2,4]triazolo[4,3-a]quinoxaline 
• 76261-60-4 2,3-bis(methylthio)quinoxaline 
• 73029-86-4 2,3-bis(hydrazino)quinoxaline 
• 693794-96-6 6-phenyl-6H-indolo[2,3-b]quinoxaline 
• 1620194-38-8 6-(p-tolyl)-6H-indolo[2,3-b]quinoxaline 
• 1620194-39-9 6-(4-fluorophenyl)-6H-indolo[2,3-b]quinoxaline 
• 1620194-40-2 6-(3-(trifluoromethyl)phenyl)-6H-indolo[2,3-b]quinoxaline 
• 1620194-41-3 6-(4-methoxyphenyl)-6H-indolo[2,3-b]quinoxaline 
• 1620194-42-4 6-(3,5-dimethoxyphenyl)-6H-indolo[2,3-b]quinoxaline 
• 1620194-43-5 6-(4-(methylthio)phenyl)-6H-indolo[2,3-b]quinoxaline 

Relevant academic research and scientific papers

Synthesis, biological evaluation, and molecular docking of new series of antitumor and apoptosis inducers designed as VEGFR-2 inhibitors

Based on quinazoline, quinoxaline, and nitrobenzene scaffolds and on pharmacophoric features of VEGFR-2 inhibitors, 17 novel compounds were designed and synthesised. VEGFR-2 IC50 values ranged from 60.00 to 123.85 nM for the new derivatives compared to 54.00 nM for sorafenib. Compounds 15a, 15b, and 15d showed IC50 from 17.39 to 47.10 μM against human cancer cell lines; hepatocellular carcinoma (HepG2), prostate cancer (PC3), and breast cancer (MCF-7). Meanwhile, the first in terms of VEGFR-2 inhibition was compound 15d which came second with regard to antitumor assay with IC50 = 24.10, 40.90, and 33.40 μM against aforementioned cell lines, respectively. Furthermore, Compound 15d increased apoptosis rate of HepG2 from 1.20 to 12.46% as it significantly increased levels of Caspase-3, BAX, and P53 from 49.6274, 40.62, and 42.84 to 561.427, 395.04, and 415.027 pg/mL, respectively. Moreover, 15d showed IC50 of 253 and 381 nM against HER2 and FGFR, respectively.

A new method for the three-step synthesis of the drug molecule 3-(2-thiophene-2-methylene)hydrazinoquinoxaline-2-one

The present invention discloses a new method for the three-step synthesis of the pharmaceutical molecule 3- (2- thiophene-2-methylene) hydrazinoquinoxaline-2-one. This method takes quinoxaline-2-ketone as the reaction raw material, and constructs the drug molecule 3-(2-thiophene-2-methylene)hydrazinoxaline-2-one by oxidation reaction, hydrazine lysis reaction and condensation reaction. The method of the present invention is simple in means of synthesis, the reaction conditions are mild, and meet the requirements of the development of green chemistry.

Imidazopyrazine organic compound and application thereof

The invention relates to an imidazopyrazine organic compound and application thereof. The organic compound has a structure as shown in a general formula (1). The organic compound according to the present invention has excellent hole transport properties and stability, can be used as a hole injection layer material in an organic electroluminescent element, and can also be doped in a hole injectionlayer or a hole transport layer as a doping agent, so that a device can be driven at a low voltage, the electroluminescent efficiency can be improved, and the service life of the device can be prolonged.

Design, synthesis, and molecular docking studies of new [1,2,4]triazolo[4,3-a]quinoxaline derivatives as potential A2B receptor antagonists

Abstract: Many shreds of evidence have recently correlated A2B receptor antagonism with anticancer activity. Hence, the search for an efficient A2B antagonist may help in the development of a new chemotherapeutic agent. In this article, 23 new derivatives of [1,2,4]triazolo[4,3-a]quinoxaline were designed and synthesized and its structures were confirmed by different spectral data and elemental analyses. The results of cytotoxic evaluation of these compounds showed six promising active derivatives with IC50 values ranging from 1.9 to 6.4?μM on MDA-MB 231 cell line. Additionally, molecular docking for all synthesized compounds was performed to predict their binding affinity toward the homology model of A2B receptor as a proposed mode of their cytotoxic activity. Results of molecular docking were strongly correlated with those of the cytotoxic study. Finally, structure activity relationship analyses of the new compounds were explored. Graphic abstract: [Figure not available: see fulltext.]

Triazolo[4,3-a] quinoxaline and [1,2,4]triazolo[4,3- a] quinoxaline-1-thiol-derived DNA intercalators: Design, synthesis, molecular docking, in silico ADMET profiles and anti-proliferative evaluations

In view of their DNA intercalation activities as anticancer agents, 17 novel [1,2,4]triazolo[4,3-a]quinoxaline derivatives have been designed, synthesized and evaluated against HepG2, HCT-116 and MCF-7 cells. Molecular docking studies were performed to investigate the binding modes of the proposed compounds with the DNA active site. The data obtained from biological testing highly correlated with those obtained from the molecular modeling studies. MCF-7 was found to be the most sensitive cell line to the influence of the new derivatives. In particular, compound 12d was found to be the most potent derivative of all the tested compounds against the three HepG2, HCT116 and MCF-7 cancer cell lines, with IC50 = 22.08 ± 2.1, 27.13 ± 2.2 and 17.12 ± 1.5 μM, respectively. Although this compound displayed nearly one third of the activity of doxorubicin (IC50 = 7.94 ± 0.6, 8.07 ± 0.8 and 6.75 ± 0.4 μM, respectively), it may be useful as a template for future design, optimization, and investigation to produce more potent anticancer analogs. Compounds 12a, 10c and 10d displayed very good anticancer activities against the three HepG2, HCT116 and MCF-7 cancer cell lines, with IC50 = 31.40 ± 2.8, 28.81 ± 2.4 and 19.72 ± 1.5 μM for 12a, 33.41 ± 2.9, 29.96 ± 2.5 and 24.78 ± 1.9 μM for 10c, and 37.55 ± 3.3, 30.22 ± 2.6 and 25.53 ± 2.0 μM for 10d. The most active derivatives, 10c, 10d, 10h, 12a, 12b and 12d, were evaluated for their DNA binding activities. Compound 12d displayed the highest binding affinity. This compound potently intercalates DNA at a decreased IC50 value (35.33 ± 1.8 μM), which is nearly equipotent to that of doxorubicin (31.27 ± 1.8 μM). Compounds 12a and 10c exhibited good DNA-binding affinities, with IC50 values of 39.35 ± 3.9 and 42.35 ± 3.9 μM, respectively. Finally, compounds 10d, 10h and 12b showed moderate DNA-binding affinities, with IC50 values of 50.35 ± 3.9, 57.08 ± 3.3 and 59.35 ± 3.2 μM, respectively.

One-pot, two-step synthesis of substituted triazoloquinoxalinone starting from 3-hydrazineylquinoxalin-2(1H)-one

An efficient one-pot two-step synthesis of substituted-triazolo[4,3-a]quinoxalin-4(5H)-one has been developed. The 3-hydrazineylquinoxalin-2(1H)-one reacts with respective aldehyde to afford the individual hydrazineylidene intermediate which undergoes oxidative cyclization in the presence of ferric chloride hexahydrate (FeCl3.6H2O) to affords various substituted- triazolo[4,3-a]quinoxalin-4(5H)-one in good to excellent yields.

Anti-MRSA drug discovery by ligand-based virtual screening and biological evaluation

S. aureus resistant to methicillin (MRSA) is one of the most-concerned multidrug resistant bacteria, due to its role in life-threatening infections. There is an urgent need to develop new antibiotics against MRSA. In this study, we firstly compiled a data set of 2,3-diaminoquinoxalines by chemical synthesis and antibacterial screening against S. aureus, and then performed cheminformatics modeling and virtual screening. The compound with the Specs ID of AG-205/33156020 was discovered as a new antibacterial agent, and was further identified as a Gyrase B (GyrB) inhibitor. In light of the common features, we hypothesized that the 6c as the representative of 2,3-diaminoquinoxalines also inhibited GyrB and eventually proved it. Via molecular docking and molecular dynamics simulations, we identified binding modes of AG-205/33156020 and 6c to the ATPase domain of GyrB. Importantly, these GyrB inhibitors inhibited the MRSA strains and showed selectivity to HepG2 and HUVEC. Taken together, this research work provides an effective ligand-based computational workflow for scaffold hopping in anti-MRSA drug discovery, and discovers two new GyrB inhibitors that are worthy of further development.

Structural investigation, DNA interactions and in?vitro anticancer studies of transition metal complexes of 3-(2-(2, 4-dihydroxy benzylidene) hydrazinyl) quinoxalin-2(1H) -one

The Schiff base ligand, 3-(2-(2, 4-dihydroxybenzylidene) hydrazinyl) quinoxalin-2(1H)-one (RHQO) has been synthesized and characterized by spectral and single crystal X-ray analysis. The Mn(II), Ni(II) and Cu(II) complexes of RHQO have been synthesized and characterized by FT-IR, UV-VIS, mass, EPR spectra, CHN, thermo gravimetric analysis, magnetic susceptibility and conductivity measurements. The morphology of the ligand and complexes is studied by Scanning Electron Microscopy. The metal complexes formed were found to be polymeric in nature. The abilities of the ligand and its metal complexes to interact and bind with calf thymus DNA (CT-DNA) has been studied by electronic absorption spectroscopy and their quantitative binding strength was evaluated in terms of their intrinsic binding constant (Kb). The cleavage interaction of the ligand and its metal complexes with super coiled pBR 322 DNA has been investigated by agarose gel electrophoresis. Cytotoxicity of the Cu(II) and Ni(II) complexes was evaluated using various cancer cell lines, Human cervical cancer cell line (Hela), B16 melanoma F10(B16-F10), Human ovarian cancer cell (SKOV3) and Breast cancer cell line (MCF7) by MTT assay. The results indicated that the ligand and its metal complexes bind with CT-DNA by groove binding mode and cleaved the supercoiled pBR 322 DNA in to nicked form. The Ni(II) and Cu(II) complexes exhibited anticancer activity without affecting the normal CHO-K1 cell lines. Communicated by Vsevolod Makeev.

New quinoxaline derivatives as VEGFR-2 inhibitors with anticancer and apoptotic activity: Design, molecular modeling, and synthesis

New series of [1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one and [1,2,4]triazolo[4,3-a]quinoxaline derivatives have been designed, synthesized, and biologically assessed for their anti-proliferative activities against two selected tumor cell lines MCF-7 and HepG2. Comparing to sorafenib (IC50 = 2.17 ± 0.13 and 3.51 ± 0.21 μM against MCF-7 and HepG2, respectively), compound 25d, 25e, 25i, and 27e exhibited the highest activities against the examined cell lines with IC50 values extending from 4.1 ± 0.4 to 11.7 ± 1.1 μM. Furthermore, VEGFR-2 inhibitory activities were assessed for all the synthesized compounds as potential mechanisms for their anti-proliferative activities. Compounds 25d, 25e, 25i, and 27e displayed prominent inhibitory efficiency versus VEGFR-2 kinase with IC50 value ranging from 3.4 ± 0.3 to 6.8 ± 0.5 nM. Fascinatingly, the results of VEGFR-2 inhibitory assays were matched with that of the cytotoxicity data, where the most potent anti-proliferative derivatives exhibited promising VEGFR-2 inhibitory activities. Further studies displayed the ability of compound 25d to induce apoptosis in HepG2 cells and can arrest the growth of such cells at the G2/M phase. Also, compound 25d produced a significant increase in the level of BAX/Bcl-2 ratio (3.8-fold), caspase- 3 (1.8-fold), and caspase-9 (1.9-fold) compared to the control cells. Molecular docking studies were carried out to investigate the possible binding interaction inside the active site of the VEGFR-2.

New bis([1,2,4]triazolo)[4,3-a:3′,4′-c]quinoxaline derivatives as VEGFR-2 inhibitors and apoptosis inducers: Design, synthesis, in silico studies, and anticancer evaluation

A new series of bis([1,2,4]triazolo)[4,3-a:3′,4′-c]quinoxaline derivatives were designed and synthesized to have the main essential pharmacophoric features of VEGFR-2 inhibitors. VEGFR-2 inhibitory activities were assessed for the designed compounds. In addition, cytotoxic activity was evaluated for all derivatives against two human cancer cell lines namely, HepG-2 and MCF-7. The most cytotoxic compound 20 h was subjected to further biological investigations including cell cycle, apoptosis, caspase-3, caspase-9, BAX, and Bcl-2 analyses. Different in silico studies as docking, ADMET and toxicity were carried out. The results exhibited that compounds 20b, 20e, 20h and 20m showed promising VEGFR-2 inhibitory activities with IC50 values of 5.7, 6.7, 3.2, and 3.1 μM, respectively. Moreover, these promising members exhibited the highest antiproliferative activities against the two cell lines with IC50 values ranging from 3.3 to 14.2 μM, comparing to sorafenib (IC50 = 2.17 and 3.43 μM against HepG2 and MCF-7, respectively). Additionally, compound 20h induced cell cycle arrest of HepG2 cells at G2/M phase. Also, such compound increased the progress of apoptosis by 3.5-fold compared to the control. As well, compound 20h showed a significant increase in the level of caspase-3 (2.07-fold), caspase-9 (1.72-fold), and BAX (1.83-fold), and a significant decrease in Bcl-2 level (1.92-fold). The in silico studies revealed that the synthesized compounds have binding pattern like that of sorafenib.