61645-34-9

Usage

Chemical Properties

Pink to orange solid

InChI:InChI=1/C8H8N4/c9-12-8-5-10-6-3-1-2-4-7(6)11-8/h1-5H,9H2,(H,11,12)

Upstream product

• 1448-87-9 2-chloroquinoxaline 
• 6962-54-5 quinoxaline-2(1H)-thione 
• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 95-54-5 1,2-diamino-benzene 

Downstream Products

• 92096-85-0 N-[1-Phenyl-1-pyridin-2-yl-meth-(Z)-ylidene]-N'-quinoxalin-2-yl-hydrazine 
• 1448-87-9 2-chloroquinoxaline 
• 1196-57-2 2-hydroxyquinoxaline 
• 1551491-98-5 (E)-2-(2-(2,6-dichlorobenzylidene)hydrazinyl)quinoxaline 
• 1551492-01-3 (E)-2-(2-(2,4-dichlorobenzylidene)hydrazinyl)quinoxaline 
• 1551492-04-6 (E)-2-(2-(3,4-dichlorobenzylidene)hydrazinyl)quinoxaline 
• 1551492-24-0 (E)-2-(2-(2-nitrobenzylidene)hydrazinyl)quinoxaline 

Relevant academic research and scientific papers

Synthesis of PJOV56, a new quinoxalinyl-hydrazone derivative able to induce autophagy and apoptosis in colorectal cancer cells, and related compounds

Quinoxaline derivatives are reported as antineoplastic agents against a variety of human cancer cell lines, with some compounds being submitted to clinical trials. In this work, we report the synthesis, characterization and cytotoxicity potential of a new series of quinoxalinyl-hydrazones. The most cytotoxic compound was (E)-2-[2-(2-pyridin-2-ylmethylene)hydrazinyl]quinoxaline (PJOV56) that presented a time-dependent effect against HCT-116 cells. After 48 h of incubation, PJOV56 was able to induce autophagy and apoptosis of HCT-116 cells, mediated by upregulation of Beclin 1, upregulation of LC3A/B II and activation of caspase 7. Apoptosis was induced along with G0/G1 cell cycle arrest at the highest concentration of PJOV56 (6.0 μM). Thus, PJOV56 showed a dose-dependent mode of action related to induction of autophagy and apoptosis in HCT-116 cells.

New chromogenic and fluorescent probes for anion detection: Formation of a [2 + 2] supramolecular complex on addition of fluoride with positive homotropic cooperativity

(Figure Presented) Two new chromogenic and fluorescent probes for anions have been designed, synthesized, and characterized. These probes contain multiple hydrogen bonding donors including hydrazine, hydrazone, and hydroxyl functional groups for potential anion interacting sites. Despite the possible flexible structural framework due to the presence of sp3 carbon linkage, X-ray structure analysis of probe 2 displayed an essentially planar conformation in the solid state owing to strong crystal packing interactions comprising a combination of favorable π-π stacking effect and hydrogen bonding to cocrystallized CH3OH molecules. Both probes 1 and 2 display orange color in DMSO solution and show fairly weak fluorescence at room temperature. Binding studies revealed that both probes 1 and 2 show noticeable colorimetric and fluorescent responses only to F-, OAc-, and H2PO4- among the nine anions tested (F -, Cl-, Br-, I-, OAc-, H2PO4-, HSO4-, ClO 4-, and NO3-). The general trend of the sensitivity to anions follows the order of F- > OAc - > H2PO4- > Cl- > Br- ≈ I- ≈ HSO4- ≈ ClO4- ≈ NO3-. A 1:2 (probe to anion) binding stoichiometry was found for probe 1 with OAc- and H2PO4- and probe 2 with F-, OAc -, and H2PO4-. The binding isotherm of probe 1 to F- was found to be complicated with apparent multiple equilibria occurring in solution. The formation of an aggregated supramolecular complex upon addition of fluoride is proposed to rationalize the observed optical responses and is supported by ESI mass spectrometry and pulsed-field gradient NMR spectroscopy. Data analysis suggests that the binding of probe 1 to F- shows positive homotropic cooperativity.

Design and Synthesis of Some New N-Phenyl-[1,2,4]triazolo[4,3-a]quinoxaline-1-sulfonamide Derivatives and Their Anti-Cancer Activity

Abstract: Synthesis of some new derivatives of N-phenyl-[1,2,4]triazolo [4,3-a]quinoxaline-1-sulfonamide and their in vitro anticancer activity on four human cancer lines like MCF-7 (human breast cancer cell line), HeLa (human cervical cancer cell line), A549 (human lung cancer cell line), and IMR32 (human neuroblastoma cell line) have been studied. Among the products, N-(3,5-dichloronitrophenyl)-[1,2,4] triazolo[4,3-a]quinoxaline-1-sulfonamide, is characterized by the activity higher than the standard Etoposide against the tested cancer cell lines.

Multifunctional quinoxaline-hydrazone derivatives with acetylcholinesterase and monoamine oxidases inhibitory activities as potential agents against Alzheimer’s disease

Multitarget molecules are considered as an effective way for the treatment of AD, instead of the classic one-drug-one-target strategy because of the multifactorial nature of AD. A variety of studies indicate that several enzymes inhibitors can be useful in the treatment of AD, including acetylcholinesterase (AchE), butyrylcholinesterase (BuChE) and monoamine oxidase (MAO). Various substituted quinoxaline-hydrazone derivatives were synthesized, and their activity in vitro were investigated, including AChE/BuChE inhibitory activity and MAOA/B inhibitory activity. Based on the experimental results, compound 5l exhibited good inhibitory potency on both AchE (IC50 = 0.028 ± 0.001 μM) and monoamine oxidase B (IC50 = 0.046 ± 0.002 μM). Molecular modeling studies showed that 5l could bind to the active site of AChE and MAO-B. Taken together, these results suggested that compound 5l might be a potential multifunctional agent for the treatment of AD.

Metal free [4+1] and [5+1] annulation reactions to prepare heterocycles using DMF and its derivatives as one-carbon source

1,2,4-Triazolo[3,4-a]pyridines and related heterocycles and substituted triazines were commonly discovered scaffolds in a variety of pharmaceutical and agrochemical agents. Herein, we report a highly efficient and practical method using DMF and its derivative for the [4+1] and [5+1] annulation reactions to prepare these heterocycles. This metal free reaction takes advantages of shelf stable DMF as solvent and carbon donor, imidazole chloride as a catalyst, the mild reaction condition tolerates a broad substrate range and substitutes. The prepared 3-unsubstituted 1,2,4-triazolo[3,4-a]pyridine and derivatives allow further introduction of a variety of functional group1 at 3-position.

Design, synthesis and biological evaluation of (E)-2-(2-arylhydrazinyl) quinoxalines, a promising and potent new class of anticancer agents

A series of forty-seven quinoxaline derivatives, 2-(XYZC6H 2CHN-NH)-quinoxalines, 1, have been synthesized and evaluated for their activity against four cancer cell lines: potent cytotoxicities were found (IC50 ranging fro

HYDRAZIDE CONTAINING NUCLEAR TRANSPORT MODULATORS AND USES THEREOF

The invention generally relates to nuclear transport modulators, e.g., CRM1 inhibitors, and more particularly to a compound represented by structural formula (I): or a pharmaceutically acceptable salt thereof, wherein the values and alternative values for the variables are as defined and described herein. The invention also includes the synthesis and use of a compound of structural formula I, or a pharmaceutically acceptable salt or composition thereof, e.g., in the treatment, modulation and/or prevention of physiological conditions associated with CRM1 activity.

SUBSTITUTED DIHYDROPYRAZOLONES AND USE THEREOF AS HIF-PROLYL-4 -HYDROXYLASE INHIBITORS

The present application relates to novel substituted dihydropyrazolone derivatives, processes for their preparation, their use for treatment and/or prophylaxis of diseases and their use for the preparation of medicaments for treatment and/or prophylaxis of diseases, in particular cardiovascular and hematological diseases and kidney diseases, and for promoting wound healing.

THE SYNTHESES OF NOVEL 2-(2-QUINOXALINYL)PYRIDAZIN-3(2H)-ONES

The first syntheses of 4-chloro-2-(2-quinoxalinyl)-pyridazin-3(2H)-one derivatives are reported.They could be synthesized from 2-hydrazinoquinoxaline derivatives as starting materials.

O-Alkyl-S-[3-oxo-1,2,4-triazolobenzopyrazin(2)yl-methyl]-(thiono)thiolphosphoric(phosphonic) acid esters

O-Alkyl-S-[3-oxo-1,2,4-triazolobenzopyrazin(2)yl-methyl]-(thiono)thiolphosphoric(phosphonic) acid esters of the formula STR1 in which R is alkyl with 1 to 4 carbon atoms, R1 is alkyl or alkoxy with 1 to 4 carbon atoms, and X is oxygen or sulfur, Which possess insecticidal properties.