Oxidative synthesis of ortho-quinones from hydroxy-PAHs by stabilized formulation of 2-iodoxybenzoic acid (SIBX)

Tiruye, Hiwot M.; Jørgensen, Kåre B.

doi:10.1016/j.tet.2022.133144

Cited by 5 publications

(7 citation statements)

References 51 publications

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“…β-Glucuronidase from Escherichia coli (140 U/mg, Millipore-Sigma, St. Louis, MO) and sulfatase from Helix pomatia (200 units/mL, Millipore-Sigma, St. Louis, MO) were stored at 4 °C in a dark environment. 1,2- and 5,6-Quinones of chrysene (CHQ) were synthesized photochemically as described in Tiruye and Jørgensen, while 1,2-catechol (CAT) of chrysene was synthesized by the reduction of 1,2-quinone using NaBH 4 based on the methods of Platt and Oesch and by photochemical cyclization of the corresponding 1,2-dimethoxy stilbene (detailed description in the Supporting Information). Both methods gave 1,2-CAT, fully characterized by nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS) analyses.…”

Section: Methodsmentioning

confidence: 99%

Relationships between Isomeric Metabolism and Regioselective Toxicity of Hydroxychrysenes in Embryos of Japanese Medaka (Oryzias latipes)

Tanabe

Pampanin

Tiruye

et al. 2022

Environ. Sci. Technol.

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Oxygenated polycyclic aromatic hydrocarbons (oxy-PAHs) are ubiquitous contaminants that can be formed through oxidation of parent PAHs. Our previous studies found 2hydroxychrysene (2-OHCHR) to be significantly more toxic to Japanese medaka embryos than 6-hydroxychrysene (6-OHCHR), an example of regioselective toxicity. We have also previously identified a sensitive developmental window to 2-OHCHR toxicity that closely coincided with liver development, leading us to hypothesize that differences in metabolism may play a role in the regioselective toxicity. To test this hypothesis, Japanese medaka embryos were treated with each isomer for 24 h during liver development (52−76 hpf). Although 6-OHCHR was absorbed 97.2 ± 0.18% faster than 2-OHCHR, it was eliminated 57.7 ± 0.36% faster as a glucuronide conjugate. Pretreatment with cytochrome P450 inhibitor, ketoconazole, reduced anemia by 96.8 ± 3.19% and mortality by 95.2 ± 4.76% in 2-OHCHR treatments. Formation of chrysene-1,2-diol (1,2-CAT) was also reduced by 64.4 ± 2.14% by ketoconazole pretreatment. While pretreatment with UDP-glucuronosyltransferase inhibitor, nilotinib, reduced glucuronidation of 2-OHCHR by 52.4 ± 2.55% and of 6-OHCHR by 63.7 ± 3.19%, it did not alter toxicity for either compound. These results indicate that CYP-mediated activation, potentially to 1,2-CAT, may explain the isomeric differences in developmental toxicity of 2-OHCHR.

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Section: Methodsmentioning

confidence: 99%

Relationships between Isomeric Metabolism and Regioselective Toxicity of Hydroxychrysenes in Embryos of Japanese Medaka (Oryzias latipes)

Tanabe

Pampanin

Tiruye

et al. 2022

Environ. Sci. Technol.

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“…C1-compounds 2-MP and 4-MP were synthesized for another project through PtCl 2 -catalyzed cyclization of the corresponding ortho -ethynylbiphenyls. 21 1 H-NMR spectra are provided in the ESI †. C2-compounds 1,7-DMP, 2,3-DMP and 2,7-DMP were resynthesized according to the procedures given by Böhme, et al 2017.…”

Section: Methodsmentioning

confidence: 99%

Alkyl-phenanthrenes in early life stage fish: differential toxicity in Atlantic haddock (Melanogrammus aeglefinus) embryos

Donald

Nakken

Sørhus

et al. 2023

Environ. Sci.: Processes Impacts

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“…The byproduct was [1,1′-binaphthalene]-2,2′-diol (Scheme 13 ) same as the byproduct catalyzed by Lewis acid. To our delight, a number of oxidants such as PIDA, 20 DMP, 21 IBX, BTI, 22 and SIBX 23 had been used for the dearomatization of β-naphthols. These oxidants can avoid the production of byproducts.…”

Section: Construction Of Carbon–nitrogen/oxygen Double Bond At the α-...mentioning

confidence: 99%

Dearomatization of α-Unsubstituted β-Naphthols

Xu,

Li,

Feng

et al. 2023

Synlett

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This Account summarizes the highly appealing dearomatization reactions of β-naphthols for the synthesis of highly functionalized, three-dimensional structures starting with simple planar aromatic compounds. The reactions are categorized mainly from the viewpoint of the construction of carbon–hydrogen, carbon–carbon, and carbon–hetero bonds (C–N/O, C–Cl, C–F) at the α-position of β-naphthols. The dearomatized products play an important role in organic synthesis and materials science.1 Introduction2 Construction of Carbon–Hydrogen Bonds at the α-Position of β-Naphthols3 Construction of Carbon–Carbon Bonds at the α-Position of β-Naphthols4 Construction of Carbon–Nitrogen/Oxygen Double Bond at the α-Position of β-Naphthols5 Construction of Carbon–Carbon and Carbon–Oxygen Bonds at the α-Position of β-Naphthols6 Construction of Carbon–Halogen Bonds at the α-Position of β-Naphthols7 Conclusion

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Oxidative synthesis of ortho-quinones from hydroxy-PAHs by stabilized formulation of 2-iodoxybenzoic acid (SIBX)

Cited by 5 publications

References 51 publications

Relationships between Isomeric Metabolism and Regioselective Toxicity of Hydroxychrysenes in Embryos of Japanese Medaka (Oryzias latipes)

Relationships between Isomeric Metabolism and Regioselective Toxicity of Hydroxychrysenes in Embryos of Japanese Medaka (Oryzias latipes)

Alkyl-phenanthrenes in early life stage fish: differential toxicity in Atlantic haddock (Melanogrammus aeglefinus) embryos

Dearomatization of α-Unsubstituted β-Naphthols

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