Synthesen mit Tetrazolo[1,5‐a]chinoxalinen

Könnecke, Andreas; Dörre, Ronald; Lippmann, Eberhard

doi:10.1002/zfch.19780180708

Cited by 7 publications

(7 citation statements)

References 10 publications

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“…The disappearance of strong absorption peak of C=O together with the presence of absorption peak at 730 cm À1 due to C-Cl confirmed the formation of compound 2 [25]. The formation of compound 3 ascertained by the appearance of absorption peak at 1578 and at 3367 cm À1 due to N-N and N-H groups of hydrazine also by the other peaks which appeared at 3.84 ppm for one proton and at 2.13 ppm for two protons of in 1 H NMR spectra [26]. In addition, compound also showed [M + 2] and [M + 4] peak in the mass spectrum.…”

Section: Resultsmentioning

confidence: 75%

“…2,3‐Dichloroquinoxaline ( 2 ) was prepared by chlorination of 2,3‐dihydroxyquinoxaline ( 1 ) , which, in turn, prepared by the condensation of the commercially available 1,2‐diaminobenzene with oxalic acid in aqueous hydrochloric acid. Treatment of ( 2 ) with hydrazine hydrate yielded 3‐hydrazino compound ( 3 ) ; finally, compound ( 3 ) was refluxed with a solution of substituted aniline in ethanol to afford substituted phenyl‐3‐hydrazinyl‐quinoxaline‐2‐amine 4a–4h) .…”

Section: Resultsmentioning

confidence: 99%

“…Calcd for C 8 H 4 Cl 2 N 2 : C, 48.28; H, 2.03; Cl, 35.62, N, 14.07. Found: C, 48.26; H, 2.04; Cl, 35.64, N, 14.Synthesis of 2-chloro-3-hydrazinyl quinoxaline (3)[26].…”

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confidence: 99%

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Synthesis of Novel Substituted Phenyl‐3‐Hydrazinyl‐Quinoxaline‐2‐Amine Derivatives: Evaluation of Antimicrobial Activity and Its Molecular Docking Studies

Paliwal

Sharma

Dwivedi

et al. 2017

Journal of Heterocyclic Chem

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New series of quinoxaline derivatives (4a–4h) were synthesized by treating 2‐chloro‐3‐hydrazinyl quinoxalin (3) with various anilines. Compound 3 was obtained from the 2,3‐dichloroquinoxaline 2 which was prepared from 4‐dihydroquinoxaline‐2,3‐dione (1). All synthesized compounds (4a–4h) were characterized by various spectral techniques, that is, IR, 1H‐NMR, mass spectroscopy, and elemental analysis and completion of reaction were confirmed by TLC. In vitro antimicrobial activity of synthesized compounds was evaluated using disc diffusion assay against gram‐positive and gram‐negative microbial strains, and then, the minimum inhibitory concentration and IC50 values of compounds were also determined. The results of antimicrobial study revealed that compounds 4e, 4g, and 4a were active and exhibited better inhibitory activities as compared with standard drug amoxicillin. Docking studies were performed by using Argus lab, and all the compounds exhibited good docking scores between −9.53 and −7.94 kcal/mol against dihydrofolate reductase protein fragment from Staphylococcus aureus (PDB ID‐4XE6). Among all compounds, 4e has shown the maximum docking score and found in agreement to in vitro studies.

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Section: Resultsmentioning

confidence: 75%

Section: Resultsmentioning

confidence: 99%

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Synthesis of Novel Substituted Phenyl‐3‐Hydrazinyl‐Quinoxaline‐2‐Amine Derivatives: Evaluation of Antimicrobial Activity and Its Molecular Docking Studies

Paliwal

Sharma

Dwivedi

et al. 2017

Journal of Heterocyclic Chem

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“…After completion of the reaction, the reaction mixture was cooled and poured onto the crushed ice. The solid product so obtained was separated and crystallized to yield 2, 3‐dihydrazinyl quinoxaline .…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, and Characterization of Quinoxaline Derivatives as a Potent Antimicrobial Agent

Dewangan¹,

Nakhate²,

Mishra³

et al. 2018

Journal of Heterocyclic Chem

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A series of quinoxalinone derivatives were synthesized by the reaction of o‐phenylenediamine with oxalic acid to yield 1, 4‐dihydro quinoxaline‐2, 3‐dione (1) and then treated with thionyl chloride to yield 2, 3 dichloro quinoxaline (2). This was further reacted with hydrazine hydrate to produce 2, 3‐dihydrazinyl quinoxaline (3). This was finally reacted with substituted aromatic aldehydes to produce 2,3‐bis[2‐(sustituted benzylidine) hydrazinyl] quinoxalines (4). These quinoxalinone derivatives were characterized by infrared spectroscopy and nuclear magnetic resonance spectroscopy and MASS spectral data. All the synthesized compounds were evaluated for their antimicrobial activity. The results of the antimicrobial study revealed that compounds 4c, 4d, and 4i were active and exhibited better inhibitory activities as compared to standard drug ciprofloxacin. The results were further checked with protein legend interaction by using docking studies, and all the compounds exhibited good docking scores between −8.72 and −11.29 kcal/mol against dihydrofolate reductase protein fragment from Staphylococcus aureus (PDB ID‐4XE6). Among all compound, 4c has shown maximum docking score and found in agreement to in vitro studies.

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“…Starting materials were purchased from Aldrich Chemical Company and used without further purification. Compounds 2 – 6 were prepared following the procedures reported in the literature [22–24]. The used intermediates (chloroacetanilides and alkyl chloroacetates) were prepared as reported [25, 26].…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Biological Evaluation of Some [1,2,4]Triazolo[4,3-a]quinoxaline Derivatives as Novel Anticonvulsant Agents

Alswah

Ghiaty

El-Morsy

et al. 2013

ISRN Organic Chemistry

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2-([1,2,4]Triazolo[4,3-a]quinoxalin-4-ylthio)acetic acid hydrazide (10) was used as a precursor for the syntheses of novel quinoxaline derivatives with potential anticonvulsant properties. The newly synthesized compounds have been characterized by IR, 1H NMR, and mass spectral data followed by elemental analysis. The anticonvulsant evaluation was carried out for eleven of the synthesized compounds using metrazol induced convulsions model and phenobarbitone sodium as a standard. Among this set of tested compounds, two of them (14, and 15b) showed the best anticonvulsant activities.

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Synthesen mit Tetrazolo[1,5‐a]chinoxalinen

Cited by 7 publications

References 10 publications

Synthesis of Novel Substituted Phenyl‐3‐Hydrazinyl‐Quinoxaline‐2‐Amine Derivatives: Evaluation of Antimicrobial Activity and Its Molecular Docking Studies

Synthesis of Novel Substituted Phenyl‐3‐Hydrazinyl‐Quinoxaline‐2‐Amine Derivatives: Evaluation of Antimicrobial Activity and Its Molecular Docking Studies

Design, Synthesis, and Characterization of Quinoxaline Derivatives as a Potent Antimicrobial Agent

Synthesis and Biological Evaluation of Some [1,2,4]Triazolo[4,3-a]quinoxaline Derivatives as Novel Anticonvulsant Agents

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