Synthesis of polybrominated diphenyl ethers via symmetrical tetra- and hexabrominated diphenyliodonium salts

Teclechiel, Daniel; Sundström, Maria; Marsh, Göran

doi:10.1016/j.chemosphere.2008.09.046

Cited by 23 publications

(16 citation statements)

References 23 publications

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“…We obtained decabromodiphenyl ether (BDE-209) from Wako. We synthesized BDE-47 according to the method of Teclechiel et al (2009), and 2,2′,3,4,4′-pentabromodiphenyl ether (BDE-85) and BDE-99 following the method of Orn et al (1996). The PBDE metabolites 4′-hydroxy-2,2′,4-tribromo diphenyl ether (4′-HO-BDE-17), 4′-methoxy-2,2′,4-tribromodiphenyl ether (4′-MeO-BDE-17), 4-hydroxy-2,2′,3,4′-tetrabromodiphenyl ether (4-HO-BDE-42), 4-methoxy-2,2′,3,4′-tetrabromo diphenyl ether (4-MeO-BDE-42), 4′-hydroxy-2,2′,4,5′-tetrabromodiphenyl ether (4′-HO-BDE-49), 4′-methoxy-2,2′,4,5′-tetrabromodiphenyl ether (4′-MeO-BDE-49), 4-hydroxy-2,2′,3,4′,5-pentabromodiphenyl ether (4-HO-BDE-90), and 4-methoxy-2,2′,3,4′,5-pentabromodiphenyl ether (4-MeO-BDE-90) were synthesized according to the method of Marsh et al (2003).…”

Section: Methodsmentioning

confidence: 99%

Nuclear Hormone Receptor Activity of Polybrominated Diphenyl Ethers and Their Hydroxylated and Methoxylated Metabolites in Transactivation Assays Using Chinese Hamster Ovary Cells

Kojima

Takeuchi

Uramaru

et al. 2009

Environ Health Perspect

215

141

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Background: An increasing number of studies are reporting the existence of polybrominated diphenyl ethers (PBDEs) and their hydroxylated (HO) and methoxylated (MeO) metabolites in the environment and in tissues from wildlife and humans. oBjective: Our aim was to characterize and compare the agonistic and antagonistic activities of principle PBDE congeners and their HO and MeO metabolites against human nuclear hormone receptors. Methods: We tested the hormone receptor activities of estrogen receptor α (ERα), ERβ, androgen receptor (AR), glucocorticoid receptor (GR), thyroid hormone receptor α 1 (TRα 1 ), and TRβ 1 against PBDE congeners BDEs 15, 28, 47, 85, 99, 100, 153, and 209, four para-HO-PBDEs, and four para-MeO-PBDEs by highly sensitive reporter gene assays using Chinese hamster ovary cells. results: Of the 16 compounds tested, 6 and 2 showed agonistic activities in the ERα and ERβ assays, respectively, and 6 and 6 showed antagonistic activities in these assays. 4´-HO-BDE-17 showed the most potent estrogenic activity via ERα/β, and 4´-HO-BDE-49 showed the most potent anti estrogenic activity via ERα/β. In the AR assay, 13 compounds showed antagonistic activity, with 4´-HO-BDE-17 in particular inhibiting AR-mediated transcriptional activity at low concentrations in the order of 10 -8 M. In the GR assay, seven compounds, including two HO-PBDEs and two MeO-PBDEs, showed weak antagonistic activity. In the TRα 1 and TRβ 1 assays, only 4-HO-BDE-90 showed weak antagonistic activity. conclusions: Taken together, these results suggest that PBDEs and their metabolites might have multiple endocrine-disrupting effects via nuclear hormone receptors, and para-HO-PBDEs, in particular, possess more potent receptor activities compared with those of the parent PBDEs and corresponding para-MeO-PBDEs. key words: androgen receptor, brominated diphenyl ether, Chinese hamster ovary cells, estrogen receptor, glucocorticoid receptor, reporter gene assay, thyroid hormone receptor.

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Section: Methodsmentioning

confidence: 99%

Nuclear Hormone Receptor Activity of Polybrominated Diphenyl Ethers and Their Hydroxylated and Methoxylated Metabolites in Transactivation Assays Using Chinese Hamster Ovary Cells

Kojima

Takeuchi

Uramaru

et al. 2009

Environ Health Perspect

215

141

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“…Due to the known biological activities of iodinated benzyl alcohols in the literature and to our interest in the chemistry and application of 1,2,3‐triiodoarenes in synthesis and medicine, we felt intrigued in examining the reactivity of 1,2,3‐triiodoarenes using MIE reactions aiming toward to the synthesis of diiodinated benzyl alcohol derivatives. In spite of the number of reports on functionalization of dibromo‐ and tribromoarene derivatives using metal–bromine exchange reactions, 21‐24, 27, 35–38 polyiodoarene derivatives remain a challenging task. A few examples of 1,2‐dihaloarene functionalization have been reported.…”

Section: Resultsmentioning

confidence: 99%

“…The regioselective metal–halogen exchange reaction of dibromo‐ and tribromoarene derivatives is well documented 21–24. 27, 35–38 Interestingly, there are only a few examples of metal–halogen exchange reactions with diiodoarenes and triiodoarenes 8. 20, 39, 40 This lack of investigations could be attributed to the accessibility and availability of diiodo‐ and triiodoarenes.…”

Section: Introductionmentioning

confidence: 99%

Efficient and Selective Synthesis of α,β‐Epoxy‐γ‐Butyrolactones from 2‐Peroxy‐1,4‐Dicarbonyl Compounds

Liu

et al. 2012

Chemistry An Asian Journal

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“…The regioselective metal-halogen exchange reaction of dibromo-and tribromoarene derivatives is well documented. [21][22][23][24]27,[35][36][37][38] Interestingly, there are only a few examples of the metal-halogen exchange reaction on diiodoarenes and triiodoarenes. 8,20,39,40 This lack of investigations could be attributed to the accessibility and availability of diiodo-and triiodoarenes.…”

Section: Introductionmentioning

confidence: 98%

Terminal versus Internal Diiodobenzyl Alcohol Derivatives via Regioselective Metal–Iodine Exchange of 1,2,3‐Triiodoarenes: Synthesis and Antibacterial Activity

et al. 2015

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A wide range of unique diiodobenzyl alcohol building blocks have been synthesized by regioselective Metal-Iodine Exchange reaction (MIE) using isopropylmagnesium chloride is reported. Remarkably, the regioselectivity of the MIE reaction is easily controlled by both the aldehydes and the 1,2,3-triiodoarenes to provide either the internal or the terminal products in good yields and in high regioselective fashion. The synthesized diiodobenzyl alcohols were tested for in vitro antibacterial activity against two Gram positive Micrococcus luteus (ATCC 934) and Staphylococcus aureus (ATCC 29213) and two Gram negative Escherichia coli (ATCC 25922) and Serratia marcescens (ATCC 27117). The biological data clearly shows that all tested diiodobenzyl alcohols have selective antibacterial activity against Gram positive strains and no activity against Gram negative ones. This report discloses a facile protocol for the synthesis of hitherto unknowns ortho-diiodobenzyl alcohol and 2,3-diiodobenzyl alcohol derivatives in only one step that is quite general in scope, scalable and hard to make by any other means. AbstractA wide range of unique diiodobenzyl alcohol building blocks have been synthesized by regioselective Metal-Iodine Exchange reactions (MIE) using isopropylmagnesium chloride is reported. Remarkably, the regioselectivity of the MIE reaction is easily controlled by both the aldehydes and the 1,2,3-triiodoarenes to provide either the internal or the terminal products in good yields and in high regioselective fashion. The synthesized diiodobenzyl alcohols were tested for in vitro antibacterial activity against two Gram positive Micrococcus luteus (ATCC 934) and Staphylococcus aureus (ATCC 29213) and two Gram negative Escherichia coli (ATCC 25922) and Serratia marcescens (ATCC 27117). The biological data clearly shows that all tested diiodobenzyl alcohols have selective antibacterial activity against Gram positive strains and no activity against Gram negative ones. This report discloses a facile protocol for the synthesis of hitherto unknowns ortho-diiodobenzyl alcohol and 2,3-diiodobenzyl alcohol derivatives in only one step that is quite general in scope, scalable and hard to make by any other means.

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Synthesis of polybrominated diphenyl ethers via symmetrical tetra- and hexabrominated diphenyliodonium salts

Cited by 23 publications

References 23 publications

Nuclear Hormone Receptor Activity of Polybrominated Diphenyl Ethers and Their Hydroxylated and Methoxylated Metabolites in Transactivation Assays Using Chinese Hamster Ovary Cells

Nuclear Hormone Receptor Activity of Polybrominated Diphenyl Ethers and Their Hydroxylated and Methoxylated Metabolites in Transactivation Assays Using Chinese Hamster Ovary Cells

Efficient and Selective Synthesis of α,β‐Epoxy‐γ‐Butyrolactones from 2‐Peroxy‐1,4‐Dicarbonyl Compounds

Terminal versus Internal Diiodobenzyl Alcohol Derivatives via Regioselective Metal–Iodine Exchange of 1,2,3‐Triiodoarenes: Synthesis and Antibacterial Activity

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