ChemInform Abstract: Quinoxaline, Its Derivatives and Applications: A State of the Art Review

Pereira, Joana A.; Pessoa, Ana M.; Cordeiro, M. Natália D. S.; Fernandes, Rita; Prudêncio, Cristina; Noronha, João Paulo; Vieira, Mónica

doi:10.1002/chin.201532268

Cited by 4 publications

(4 citation statements)

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“…This means that they adsorb poorly to PUF and biomass. Furthermore, quinoxalines are known as antifunga l agents, which means that it is not expected that T. versicolor can use them as nutrients [27].…”

Section: Resultsmentioning

confidence: 99%

Removal of toluene diamine and its derivatives from polyurethane foam using immobilized Trametes versicolor

2019

Adv. Environ. Biol

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Background: In addition to uses in home furnishings and the construction sector, polyurethane foam (PUF) is also prevalent in medical products such as scaffolds and implants. However, these applications raise concerns for human health as the use of this material can result in exposure to the carcinogenic substance 2,4-toluenediamine (2,4-TDA). The objective of this study was to identify easily extracted PUF-residuals and to study the removal of them in a biodegradation experiment including immobilized Trametes versicolor. Ultra-high-performance liquid chromatography-quadrupole/time of flight mass spectrometry (UHPLC-Q-TOF MS) was used in MS and MS/MS-mode to confirm the identities of PUF-related compounds and follow their concentration changes. Results: Except for 2,4-TDA and 2,6-TDA which were confirmed by standards, previously not reported substances were tentatively identified, among them TDA-dimers. These dimers include homodimers, heterodimers containing 2,4-TDA and 2,6-TDA and compounds that are hydroxylated. The experiments that were performed in an acidic fungal culture revealed a not previously described removal of these compounds below the approximate nM detection limit. The mechanisms behind their removal may include biosorption to fungal mycelia, bioaccumulation, use of them as nutrients or extracellular catabolism. Conclusion: The results of this study not only highlight the ease by which harmful compounds were extracted from the investigated PUF-quality which is used in non-medical applications, but also the possibility to use fungal-based methods to eliminate them. This could be facilitated by an initial extraction of PUF (excluding fungi) followed by a removal of the substances with PUF-immobilized Trametes versicolor. The findings in this study may be of interest to further investigate PUF-residuals in products aimed for medical applications.Citation: Åke Stenholm et al., 2019. Removal of toluene diamine and its derivatives from polyurethane foam using immobilized Trametes versicolor. Advances in Environmental Biology 13(2): 17-29.

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Section: Resultsmentioning

confidence: 99%

Removal of toluene diamine and its derivatives from polyurethane foam using immobilized Trametes versicolor

2019

Adv. Environ. Biol

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“…Quinoxaline derivates are a class of heterocyclic compounds and have been shown to have diverse applications in medicine due to their biological activities. In addition to their known anti-microbial, anti-inflammatory, anti-cancer, anti-depressant, and anti-diabetic activities [7], quinoxaline derivatives also demonstrate anti-plasmodial properties. A Novartis chemical library screen identified BQR695 (2-[[7-(3,4-dimethoxyphenyl)quinoxalin-2-yl]amino]-Nmethylacetamide) as an anti-plasmodial compound that acts through inhibition of PfPI4kinase [8].…”

Section: Introductionmentioning

confidence: 99%

Quinoxaline-Based Anti-Schistosomal Compounds Have Potent Anti-Malarial Activity

Rawat,

Padalino,

Yeo

et al. 2024

Preprint

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The human pathogens Plasmodium and Schistosoma are each responsible for over 200 million infections annually, being particularly problematic in low- and middle-income countries. There is a pressing need for new drug targets for these diseases, driven by emergence of drug-resistance in Plasmodium and the overall dearth of new drug targets for Schistosoma. Here, we explored the opportunity for pathogen-hopping by evaluating a series of quinoxaline-based anti-schistosomal compounds for activity against P. falciparum. We identified compounds with low nanomolar potency against 3D7 and multidrug-resistant strains. Evolution of resistance using a mutator P. falciparum line revealed a low propensity for resistance. Only one of the series, compound 22, yielded resistance mutations, including point mutations in a non-essential putative hydrolase pfqrp1,as well as copy-number amplification of a phospholipid-translocating ATPase pfatp2, a potential target. Notably, independently generated CRISPR-edited mutants in pfqrp1 also showed resistance to compound 22 and a related analogue. Moreover, previous lines with pfatp2 copy-number variations were similarly less susceptible to challenge with the new compounds. Finally, we examined whether the predicted hydrolase activity of PfQRP1 underlies its mechanism of resistance, showing that both mutation of the putative catalytic triad and a more severe loss of function mutation elicited resistance. Collectively, we describe a compound series with potent activity against two important pathogens and their potential target in P. falciparum.

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“…The quinoxaline and benzoxazine derivatives are mainly known for their wide range of pharmacological and biological activities. [1][2][3] Their ring moieties are part of the chemical structures of various antibiotics such as echinomycin, levomycin and actinomycin. 2 Such compounds are also known to be active against transplant tumors.…”

Section: Introductionmentioning

confidence: 99%

“…[1][2][3] Their ring moieties are part of the chemical structures of various antibiotics such as echinomycin, levomycin and actinomycin. 2 Such compounds are also known to be active against transplant tumors. 4 Also, quinoxaline-based compounds have the ability to inhibit the metal corrosion and they are used in electroluminescent materials.…”

Section: Introductionmentioning

confidence: 99%

Experimental and computational analysis (DFT method) of some quinoxalinones and benzoxazinones: spectroscopic investigation (FT-IR, FT-Raman, UV-Vis, NMR)

et al. 2019

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The selected quinoxalinones and benzoxazinones derivatives, synthesized in our laboratory earlier, were explored by spectroscopic techniques (UV-Vis, IR, Raman and NMR) and theoretical study (DFT calculations). In order to understand the electronic properties of these compounds, the theoretical UV spectra have been investigated by TDDFT/B3LYP method with 6-311?G(d,p) basis set in ethanol as a solvent. For all compounds, the absorption of UV radiation with a wavelength around 415 nm with an oscillator strength f = 0.90 induces the intramolecular electronic transition (n?p*). The frontiers molecular orbitals are calculated, and contributions of the electronic transitions are determined. Also, we did quantum chemical calculations to investigate the corrosion inhibition properties of these molecules. The vibrational analysis was performed at the B3LYP/6-311?G(d,p) level of theory in vacuo. Obtained results are in very good agreement with experimental data. The calculated 13 C NMR shifts in all cases are in good-to-excellent agreement. Also, 1 H NMR predicted shifts are comparable with experimental results, but there are some deviations (for N-H shifts) probably as a consequence of intramolecular interactions.

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ChemInform Abstract: Quinoxaline, Its Derivatives and Applications: A State of the Art Review

Abstract: Quinoxaline, Its Derivatives and Applications: A State of the Art Review -[63 refs. + subrefs.]. -(PEREIRA, J. A.; PESSOA, A. M.; CORDEIRO, M. N. D. S.; FERNANDES, R.; PRUDENCIO, C.; NORONHA, J. P.; VIEIRA*, M.; Eur. J. Med. Chem. 97 (2015) 664-672, http://dx.

Cited by 4 publications

References 1 publication

Removal of toluene diamine and its derivatives from polyurethane foam using immobilized Trametes versicolor

Removal of toluene diamine and its derivatives from polyurethane foam using immobilized Trametes versicolor

Quinoxaline-Based Anti-Schistosomal Compounds Have Potent Anti-Malarial Activity

Experimental and computational analysis (DFT method) of some quinoxalinones and benzoxazinones: spectroscopic investigation (FT-IR, FT-Raman, UV-Vis, NMR)

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