1448-87-9Relevant academic research and scientific papers
Synthesis of new quinoxaline derivatives
Makhloufi,Baitiche,Merbah,Benachour
, p. 3532 - 3540 (2011)
New quinoxaline derivatives were prepared by the reaction of 2-hydroxyquinoxaline 1 and alkyl or alkylaminoalkyl halides in dimethylformamide using potassium carbonate as a base. The hydroxyl group was readily converted into a thiol function by treatment with phosphorus pentasulfide and/or Lawesson's reagent in pyridine, and the subsequent alkylation of the thiol group was carried out under phase-transfer catalyst conditions. Chlorination of 1 was carried out with phosphorus oxychloride. Branching of alkylamino side chains to the 2-OH, 2-SH, and 2-Cl quinoxalines resulted in the synthesis of several compounds. Synthesis and alkylation of 2-hydroxy 7-nitroquinoxaline are also reported.
An improved method for chlorination of nitrogen-containing π-deficient heteroaromatics using triphenylphosphine and trichloroisocyanuric acid
Sugimoto, Osamu,Tanji, Ken-ichi
, p. 181 - 185 (2005)
Phosphorus compound prepared by reaction of triphenylphosphine with trichloroisocyanuric acid was found to be applied to chlorination of nitrogen-containing π-deficient heteroaromatics. As self-decomposition of the chlorinating reagent hardly proceeds, the reagent is more useful than phosphorus compound prepared by triphenylphosphine and N-chlorosuccinimide.
Synthesis and antimicrobial activity of some 2(1H)-quinoxalinone-6-sulfonyl derivatives
Obafemi, Craig A.,Akinpelu
, p. 1795 - 1807 (2005)
The synthesis of some quinoxalinesulfonyl derivatives is described. Two of the synthesized derivatives, 2-oxo-1,2-dihydroquinoxaline-6-sulfonyl azide (3a) and 2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-sulfonyl azide (3b), were screened in vitro for their growth inhibitory activity against nine strains of Gram-positive and seven strains of Gram-negative bacteria, along with two fungal isolates. The two compounds showed broad spectrum (in vitro) activity against the bacterial strains. Copyright Taylor & Francis Inc.
Novel gas-phase cyclisation reactions of 2-(1-pyrazolyl)phenylnitrenes
Clark, Bernard A. J.,McNab, Hamish,Sommerville, Craig C.
, p. 1211 - 1212 (1996)
Flash vacuum pyrolysis of the azide 3 gives a mixture of pyrazolobenzotriazole 2, quinoxaline 5 and pyrazolobenzimidazole 4 derived from the corresponding nitrene.
Synthesis, antiviral and antibacterial activities and action mechanism of penta-1,4-dien-3-one oxime ether derivatives containing a quinoxaline moiety
Xia, Rongjiao,Guo, Tao,Chen, Mei,Su, Shijun,He, Jun,Tang, Xu,Jiang, Shichun,Xue, Wei
, p. 16461 - 16467 (2019)
A series of penta-1,4-dien-3-one oxime ether derivatives containing a quinoxaline moiety were synthesized and their antibacterial and antiviral activities were evaluated. Bioassay activity indicated that some of the compounds displayed significant antibacterial and antiviral activities. In particular, some title compounds were found to show remarkable antiviral activities against tobacco mosaic virus (TMV). Compound 6i showed remarkable curative, protective and inactivation activity against TMV, with a 50% effective concentration (EC50) of 287.1, 157.6 and 133.0 μg mL-1, respectively. These results were better than or comparable to those of ningnanmycin (356.3, 233.7 and 121.6 μg mL-1, respectively). Microscale thermophoresis (MST) also showed that the binding of compound 6i to TMV coat protein (TMV-CP) gave a Kd value of 0.115 ± 0.092 μmol L-1, which was better than that of ningnanmycin (0.523 ± 0.254 μmol L-1). Meanwhile, the EC50 values of compound 6k against Xanthomonas axonopodis pv. Citri (Xac) and Xanthomonas oryzae pv. oryzae (Xoo) were 16.8 and 33.4 μg mL-1 respectively, and that of compound 6i against Ralstonia solanacearum (Rs) was 33.9 μg mL-1. These results were better than those of bismerthiazol (44.3, 42.5 and 62.4 μg mL-1, respectively). The mechanism of antibacterial action of compound 6k against Xac was analysed through scanning electron microscopy (SEM). This study indicated that the title compounds are valuable in the search for novel agrochemicals.
A Computer-Driven Scaffold-Hopping Approach Generating New PTP1B Inhibitors from the Pyrrolo[1,2-a]quinoxaline Core
García-Marín, Javier,Griera, Mercedes,Alajarín, Ramón,Rodríguez-Puyol, Manuel,Rodríguez-Puyol, Diego,Vaquero, Juan J.
, p. 2895 - 2906 (2021/07/21)
Protein tyrosine phosphatase 1B (PTP1B) is a very promising target for the treatment of metabolic disorders such as type II diabetes mellitus. Although it was validated as a promising target for this disease more than 30 years ago, as yet there is no drug in advanced clinical trials, and its biochemical mechanism and functions are still being studied. In the present study, based on our experience generating PTP1B inhibitors, we have developed and implemented a scaffold-hopping approach to vary the pyrrole ring of the pyrrolo[1,2-a]quinoxaline core, supported by extensive computational techniques aimed to explain the molecular interaction with PTP1B. Using a combination of docking, molecular dynamics and end-point free-energy calculations, we have rationally designed a hypothesis for new PTP1B inhibitors, supporting their recognition mechanism at a molecular level. After the design phase, we were able to easily synthesize proposed candidates and their evaluation against PTP1B was found to be in good concordance with our predictions. Moreover, the best candidates exhibited glucose uptake increments in cellulo model, thus confirming their utility for PTP1B inhibition and validating this approach for inhibitors design and molecules thus obtained.
Design and Synthesis of Some New N-Phenyl-[1,2,4]triazolo[4,3-a]quinoxaline-1-sulfonamide Derivatives and Their Anti-Cancer Activity
Badithapuram, Vinitha,Bandari, Srinivas,Dasari, Gouthami,Nukala, Satheesh Kumar,Pandiri, Madhuri
, p. 2280 - 2285 (2021/12/23)
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.
One-pot multicomponent synthesis of novel 2-(piperazin-1-yl) quinoxaline and benzimidazole derivatives, using a novel sulfamic acid functionalized Fe3O4 MNPs as highly effective nanocatalyst
Esam, Zohreh,Akhavan, Malihe,Bekhradnia, Ahmadreza
, (2020/10/27)
The immobilization of sulfonic acid on the surface of Fe3O4 magnetic nanoparticles (MNPs) as a novel acid nanocatalyst has been successfully reported. The morphological features, thermal stability, magnetic properties, and other physicochemical properties of the prepared superparamagnetic core–shell (Fe3O4@PFBA–Metformin@SO3H) were thoroughly characterized using Fourier transform infrared (FTIR), X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDS), field-emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), thermogravimetric analysis–differential thermal analysis (TGA-DTA), atomic force microscopy (AFM), dynamic light scattering (DLS), Brunauer–Emmett–Teller (BET), and vibrating sample magnetometer (VSM) techniques. It was applied as an efficient and reusable catalyst for the synthesis of 2-(piperazin-1-yl) quinoxaline and benzimidazole derivatives via a one-pot multiple-component cascade reaction under green conditions. The results displayed the excellent catalytic activity of Fe3O4@PFBA–metformin@SO3H as an organic–inorganic hybrid nanocatalyst in condensation and multicomponent Mannich-type reactions. The easy separation, simple workup, excellent stability, and reusability of the nanocatalyst and quantitative yields of products and short reaction time are some outstanding advantages of this protocol.
Multifunctional quinoxaline-hydrazone derivatives with acetylcholinesterase and monoamine oxidases inhibitory activities as potential agents against Alzheimer’s disease
Ilgin, Sinem,Karaduman, Abdullah Burak,Levent, Serkan,Osmaniye, Derya,?avu?o?lu, Betül Kaya,?evik, Ulviye Acar,?zkay, Yusuf,Kaplancikli, Zafer As?m,Karaburun, Ahmet ?a?r?,Sa?lik, Begüm Nurpelin,Turan, Gülhan
, p. 1000 - 1011 (2020/04/29)
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.
Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis
Wang, Jian,Li, Yan-Hui,Pan, Song-Cheng,Li, Ming-Fang,Du, Wenting,Yin, Hong,Li, Jing-Hua
supporting information, p. 146 - 153 (2020/03/10)
The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.
