SYNTHESIS OF 1<i>H</i>-BENZOXAZINE-2,4-DIONES FROM HETEROCYCLIC ANHYDRIDES: EVALUATION OF ANTIOXIDANT AND ANTIMICROBIAL ACTIVITIES

Sarmiento-Sánchez, Juan I.; Montes‐Ávila, Julio; Ochoa-Terán, Adrían; Delgado‐Vargas, Francisco; Wilson-Corral, Víctor; Díaz‐Camacho, Sylvia Páz; García-Páez, Fernando; Bastidas-Bastidas, Pedro

doi:10.5935/0100-4042.20140201

Cited by 6 publications

(3 citation statements)

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“…The synthesis of compound 3 started with a double nitrogen insertion in pyromellitic dianhydride by its reaction with trimethylsilyl azide (TMSA) as described for phthalic anhydrides. 8 The resulting complex mixture of reaction products required extensive purification efforts and only one regioisomer, 1,9-dihydro-2 H ,4 H -benzo[1,2- d :5,4- d ′]bis([1,3]oxazine)-2,4,6,8-tetraone ( 7a ), could be obtained reliably and in practical amounts. Following ring-opening by hydrolysis resulted in 4,6-diaminoisophthalic acid ( 8 ) which was esterified and cyclized to 3,7-dihydroxy-2,8-dimethylpyrido[3,2- g ]quinoline-4,6(1 H ,9 H )-dione ( 3 ) as described for compound 2 (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Beyond iron: metal-binding activity of the Pseudomonas quinolone signal-motif

Szamosvári,

Savchenko,

Badouin

et al. 2023

Org. Biomol. Chem.

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Section: Resultsmentioning

confidence: 99%

Beyond iron: metal-binding activity of the Pseudomonas quinolone signal-motif

Szamosvári,

Savchenko,

Badouin

et al. 2023

Org. Biomol. Chem.

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“…It has been hypothesized20 that one of the possible pathways for the formation of IA may be through the intramolecular nucleophilic addition of o -carboxyl benzyl isocyanate, which can be considered as an open-loop isomer of NHPI:…”

Section: Resultsmentioning

confidence: 99%

An Exceptionally Facile Two-Step Structural Isomerization and Detoxication via a Water-Assisted Double Lossen Rearrangement

Huang

Xie

et al. 2016

Sci Rep

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N-hydroxyphthalimide (NHPI), which is best known as an organocatalyst for efficient C-H activation, has been found to be oxidized by quinoid compounds to its corresponding catalytically active nitroxide-radical. Here, we found that NHPI can be isomerized into isatoic anhydride by an unusually facile two-step method using tetrachloro-1,4-benzoquinone (TCBQ, p-chloranil), accompanied by a two-step hydrolytic dechlorination of highly toxic TCBQ into the much less toxic dihydroxylation product, 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone (chloranilic acid). Interestingly, through the complementary application of oxygen-18 isotope-labeling, HPLC combined with electrospray ionization quadrupole time-of-flight and high resolution Fourier transform ion cyclotron resonance mass spectrometric studies, we determined that water was the source and origin of oxygen for isatoic anhydride. Based on these data, we proposed that nucleophilic attack with a subsequent water-assisted Lossen rearrangement coupled with rapid intramolecular addition and cyclization in two consecutive steps was responsible for this unusual structural isomerization of NHPI and concurrent hydroxylation/detoxication of TCBQ. This is the first report of an exceptionally facile double-isomerization of NHPI via an unprecedented water-assisted double-Lossen rearrangement under normal physiological conditions. Our findings may have broad implications for future research on hydroxamic acids and polyhalogenated quinoid carcinogens, two important classes of compounds of major chemical and biological interest.

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“…In modern research huge application of antioxidant plants is well recognized for several health benefits, but research works on mitochondrial antioxidant pharmacophore were not in the running until now. The pyrrole fused heterocyclic scaffolds are a central privileged guest of nature in a huge number of bioactive natural products such as lamellarins and related pyrrole-derived alkaloids like lukianols A and B, ningalins A–D, acortatarins A and B, cyclooroidin, etc., which possess antioxidant, cytotoxicity, antibiotic, and antitumor activity. − In addition to that, benzoxazine framework also serves as a spectrum of bioactivities such as antioxidant, antihyperlipidemic agents, a potent inhibitor of hepatitis C virus, and antimicrobial activity. − After critically reviewing both pyrrole and benzoxazine derivatives having antioxidant property, our motto was to unite both moieties to make a series of fused pyrrolobenzoxazine compounds that may act as an antioxidant (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Assessment of Pyrrolobenzoxazine Scaffold as a Potent Antioxidant

et al. 2019

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Reduction of mitochondrial oxidative stress-mediated diseases is an important pharmaceutical objective in recent biomedical research. In this context, a series of novel pyrrolobenzoxazines (PyBs) framework with enormous diversity (compounds 5a–w) was synthesized by employing a low-temperature greener pathway, and antioxidant property of the synthesized compounds was successfully demonstrated on preclinical model goat heart mitochondria, in vitro. Copper–ascorbate (Cu–As) was utilized as an oxidative stress generator. Out of screened PyBs, the compound possessing −OH and −OMe groups on benzene nucleus along with pyrrolobenzoxazine core moiety (compound 5w) displayed magnificent antioxidant property with a minimum effective dose of 66 μM during the biochemical assessment. The ameliorative effect of synthesized pyrrolobenzoxazine moiety on levels of biomarkers of oxidative stress, antioxidant enzyme, activities of Krebs cycle and respiratory chain enzymes, mitochondrial morphology, and Ca2+ permeability of mitochondrial membrane was investigated in the presence of Cu–As. Furthermore, the binding mode of Cu–As by compound 5w was explored successfully using isothermal titration calorimetry (ITC) analysis.

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SYNTHESIS OF 1H-BENZOXAZINE-2,4-DIONES FROM HETEROCYCLIC ANHYDRIDES: EVALUATION OF ANTIOXIDANT AND ANTIMICROBIAL ACTIVITIES

Cited by 6 publications

References 0 publications

Beyond iron: metal-binding activity of the Pseudomonas quinolone signal-motif

Beyond iron: metal-binding activity of the Pseudomonas quinolone signal-motif

An Exceptionally Facile Two-Step Structural Isomerization and Detoxication via a Water-Assisted Double Lossen Rearrangement

Synthesis and Biological Assessment of Pyrrolobenzoxazine Scaffold as a Potent Antioxidant

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