480-96-6Relevant academic research and scientific papers
Photochemistry of o-Nitrophenylazide in Matrices. The First Direct Spectroscopic Observation of o-Dinitrosobenzene
Murata, Shigeru,Tomioka, Hideo
, p. 57 - 60 (1992)
Photolysis of o-nitrophenylazide in an Ar matrix at 12 K produced the mixture of benzofuroxan and a new species, which could be identified as o-dinitrosobenzene on the basis of its IR and UV spectra.
Intramolecular interaction between ortho-azido and azoxy groups as a new way of forming a N-N bond. Synthesis of 2-alkylbenzotriazole 1-oxides
Lipilin,Karslyan,Churakov,Strelenko,Tartakovsky
, p. 1013 - 1020 (2005)
Heating of 2-(alkyl-NNO-azoxy)-1-azidobenzenes in boiling benzene gave 2-alkyl-benzotriazole 1-oxides (Alk = Me, Et, Pri, and Bu t). This first-order reaction involves an earlier unknown intramolecular interaction between the azido and azoxy groups with simultaneous release of molecular nitrogen. The cyclization rate increases in the following sequence of the alkyl groups: Me i t. Complete assignment of the signals in the 1H, 13C, and 14N NMR spectra of 2-alkylbenzotriazole 1-oxides was performed.
Mass Spectral Fragmentation of Benzofurazan-1-oxide
Dyall, Leonard K.
, p. 519 - 522 (1987)
Fragmentations in the mass spectrum of benzofurazan-1-oxide have been studied using linked scan, accelerating voltage scan and mass-analysed ion kinetic energy spectrometric techniques.Major pathways involve NO.+NO. and NO.+CO loss, these double losses occuring in such rapid succession as to appear 'concerted' in some experiments.Minor pathways are loss of CO2, C2N2O2, or C2HN2O2 from the molecular ion.The major fragment ion, m/z 76, in the conventional mass spectrum is not detected in a mass-analysed ion kinetic energy spectrometric experiment with the molecular ion until collision activation is provided.The conventional electron impact spectrum invariably includes ions from benzofurazan which is produced by thermal deoxygenation in the source.
Rates and Products of Reactions of N-Benzoyloxy-2-nitrobenzenamine with Metal Alkoxides
Dyall, Leonard K.
, p. 763 - 768 (2001)
A major pathway when N-benzoyloxy-2-nitrobenzenamine (1b) reacts with sodium methoxide is attack on carbonyl and production of methyl benzoate. In a competing pathway, proton abstraction is followed by loss of benzoate and formation of 2,1,3-benzoxadiazole N-oxide (4). With the more bulky t-butoxide base, only the latter pathway is followed, though the heterocyclic product undergoes subsequent destruction. Both the detection in the visible spectrum of a red transient intermediate, and a lack of an electron spin resonance spectrum, indicate it to be the anion (2b). The rates of the reactions of potassium t-butoxide with (1b) and N-benzoyloxy-4-nitrobenzenamine (7) are very similar, which rules out the possibility that the ortho-nitro group in (1b) provides neighbouring group assistance for loss of benzoate ion from the anion (2b). Rate measurements show that the loss of benzoate from (2b) is 39 times slower than chloride loss from the analogous anion (2a).
Discovery of novel nitrogenous heterocyclic-containing quinoxaline-1,4-di-N-oxides as potent activator of autophagy in M.tb-infected macrophages
Huang, Lingli,Lu, Qirong,Pan, Yuanhu,Qu, Wei,Xie, Shuyu,Yuan, Zonghui,Zhang, Heying,Zhang, Jie
, (2021/07/06)
As a continuation of our research on antimycobacterial agents, a series of novel quinoxaline-1,4-di-N-oxides (QdNOs) containing various nitrogenous heterocyclic moieties at the R6 position were designed and synthesized. Antimycobacterial activities, as well as the cytotoxic effects, of the compounds were assayed. Four compounds (6b, 6f, 6n, and 6o), characterized by 2-carboxylate ethyl or benzyl ester, 6-imidazolyl or 1,2,4-triazolyl, and a 7-fluorine group, exhibited the most potent antimycobacterial activity against M.tb strain H37Rv (MIC ≤ 0.25 μg/mL) with low toxicity in VERO cells (SI = 169.3–412.1). Compound 6o also exhibited excellent antimycobacterial activity in an M.tb-infected macrophage model and was selected for further exploration of the mode of antimycobacterial action of QdNOs. The results showed that compound 6o was capable of disrupting membrane integrity and disturbing energy homeostasis in M.tb. Furthermore, compound 6o noticeably increased cellular ROS levels and, subsequently, induced autophagy in M.tb-infected macrophages, possibly indicating the pathways of QdNOs-mediated inhibition of intracellular M.tb replication. The in vivo pharmacokinetic (PK) profiles indicated that compounds 6o was acceptably safe and possesses favorable PK properties. Altogether, these findings suggest that compound 6o is a promising antimycobacterial candidate for further research.
Discovery of 1,2,3-triazole based quinoxaline-1,4-di-N-oxide derivatives as potential anti-tubercular agents
Aggarwal, Himanshu,Ewa, Augustynowicz-Kopec,G?ogowska, Agnieszka,Ghosh, Balaram,Kumar, Banoth Karan,Murugesan, Sankaranarayanan,Nandikolla, Adinarayana,Pulya, Sravani,Sekhar, Kondapalli Venkata Gowri Chandra,Srinivasarao, Singireddi,Suresh, Amaroju
, (2020/05/29)
A series of thirty one novel 2-(((1-(substituted phenyl)-1H-1,2,3-triazol-4-yl)methoxy)carbonyl)-3-methylquinoxaline-1,4-dioxide (7a-l), 3-(((1-(substituted phenyl)-1H-1,2,3-triazol-4-yl)methoxy)carbonyl)-6-chloro-2-methylquinoxaline-1,4-dioxide (8a-l) and 2-(((1-(substituted phenyl)-1H-1,2,3-triazol-4-yl)methoxy)carbonyl)-6,7-dichloro-3-methylquinoxaline-1,4-dioxide (9a-g) analogues were synthesized, characterized using various analytical techniques and single crystal was developed for the compounds 8 g and 9f. Synthesized compounds were evaluated for in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv strain and two clinical isolates Spec. 210 and Spec. 192. The titled compounds exhibited minimum inhibitory concentration (MIC) ranging from 30.35 to 252.00 μM. Among the tested compounds, 8e, 8 l, 9c and 9d exhibited moderate activity (MIC = 47.6 – 52.0 μM) and 8a exhibited significant anti-tubercular activity (MIC = 30.35 μM). Furthermore, 8e, 8 l, and 9d were found to be less toxic against human embryonic kidney, HEK 293 cell lines. Finally, a docking study was also performed using MTB DNA Gyrase (PDB ID: 5BS8) for the significantly active compound 8a to know the exact binding pattern within the active site of the target enzyme.
Preparation method of mequindox
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Paragraph 0046-0063, (2019/02/08)
The invention provides a preparation method of mequindox. The preparation method comprises the step of performing reaction by taking ortho-nitroaniline, sodium hypochlorite and acetylacetone as raw materials, taking an NaOH/attapulgite compound as a catalyst and taking sodium carboxymethyl cellulose as a solubilizing agent and a homogenizing agent so as to obtain the mequindox. The preparation method of the mequindox, provided by the invention, realizes the purpose of one-step preparation of the mequindox, omits the intermediate treatment step of benzofurazan, and is simple in technology and high in production efficiency. The purity of the prepared mequindox product can reach 99% or more, and the total yield of the prepared mequindox product can reach 84.5% or more, which is equivalent tosingle-step yield of 90% or more, so that the prepared mequindox product has broad application prospects.
Improved synthesis of quinocetone and its two deoxy metabolites
Li, Yuwen,Qiu, Mei,Bai, Yubin,Qu, Shaoqi,Hao, Zhihui
, p. 265 - 270 (2018/04/12)
Oxidation of o-nitroaniline with sodium hypochlorite afforded benzofurazan oxide in 96 % yield, and treatment of benzofurazan oxide with acetylacetone in the presence of triethylamine gave 2-acetyl-3-methyl-quinoxaline--1,4-dioxide in 94 % yield. Finally, condensation of 2-acetyl-3-methyl-quinox-aline-1,4-dioxide with benzaldehyde using 4-(dimethylamino)pyridinium acetate as a catalyst led to quinocetone in 95 % yield. Subsequently, reduction of the synthesized quinocetone with sodium dithionite resulted in two deoxy derivatives, 1-(3-methyl-4-oxido-2-quinoxalinyl)-3-phenyl-2-propen-1-one and 1-(3-methyl-2-quinoxalinyl)-3-phenyl-2-propen-1-one in 88.5 and 92 % yield, respectively. Furthermore, the synthesized quinocetone, and its deoxy derivatives were characterized by1H-NMR,13C-NMR and elemental analysis.
Cu-Catalyzed π-Core Evolution of Benzoxadiazoles with Diaryliodonium Salts for Regioselective Synthesis of Phenazine Scaffolds
Sheng, Jinyu,He, Ru,Xue, Jie,Wu, Chao,Qiao, Juan,Chen, Chao
supporting information, p. 4458 - 4461 (2018/08/09)
The Cu-catalyzed regioselective synthesis of phenazine N-oxides was realized from benzoxadiazoles and diaryliodonium salts. The process was initiated by the electrophilic arylation of benzoxadiazoles with diaryliodonium salts and followed by benzocyclization reactions. The further reduction of N-oxides in situ to phenazine scaffolds and deviation to organic fluorescent materials were readily accomplished.
One-pot methodology for conversion of o-halogen nitrobenzenes to benzofuroxans
Leyva, Elisa,Leyva-Ramos, Socorro,Jiménez-Cata?o, Rogelio,de Luna-Méndez, Telma A.,Cárdenas-Chaparro, Agobardo
supporting information, p. 604 - 608 (2017/03/15)
Reaction of o-halonitrobenzenes with sodium azide under reflux of DMF/H2O gives benzofuroxans in one step in moderate to good yields. This is a faster methodology compared to the conventional procedure involving the preparation and subsequent pyrolysis of o-nitrophenyl azides. For comparison, the reaction was also performed under phase-transfer catalysis.
