Synthesis of the β-D-Glucuronides of 2,3-, 3,4-, and 2,6-Dichlorophenol

Goenechea, S.; Rüċker, G.; Hubert, Marcus A.

doi:10.1002/1521-4184(200103)334:3<101::aid-ardp101>3.0.co;2-2

Cited by 3 publications

(3 citation statements)

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“…32 In one example, C 6 H 6 -nitromethane, using 14a and with Hg(CN) 2 as catalyst, afforded an excellent yield (92%). 34 For the synthesis of a set of dichlorophenol glucuronides, Hubert et al 27 preferred 9 to 14a, despite good yields and suppression of orthoester formation with the latter, owing to deprotection issues (see section 4.1.5). Of the morphinans 25a, b only the non-basic 25b would react with 9.…”

Section: Biogenesis: Udp-glucuronosyl Transferases (Ugts)mentioning

confidence: 99%

“…Pivaloates are invariably much more slowly hydrolysed, even with NaOH, though in this author's experience this does not necessarily lead to more elimination. 71 In the synthesis of the Oglucuronides of a set of dichlorophenols (see Section 4.1.1 27 ), Hubert et al preferred acetate protection, stating that a dehydration product was formed on attempted hydrolysis of pivaloates. However, extremely vigorous conditions were used (boiling NaOMe solution, 30 h) and these would surely have exacerbated elimination.…”

Section: Oxidation Of Glucosidesmentioning

confidence: 99%

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Glucuronides from metabolites to medicines: a survey of the in vivo generation, chemical synthesis and properties of glucuronides

Stachulski

Meng

2013

Nat. Prod. Rep.

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Covering: 1998 to 2011. Previous review: Nat. Prod. Rep., 1998, 15, 173-186. The fourteen years that have passed since the previous review on this topic have seen a significant increase of interest in many aspects of glucuronide chemistry and biology. Glucuronides are the most important class of phase 2 xenobiotic metabolites and typically act in a detoxifying role. While this is generally true for O-alkyl and O-aryl glucuronides, a number of glucuronides are known to be pharmacologically active per se. Additionally the use of glucuronide prodrugs, notably to ameliorate the cytotoxicity of anticancer agents, has markedly increased. Whereas the previous review covered only the synthesis of O-glucuronides, we now include N-, S- and C-glucuronides also and discuss both synthetic and biological aspects. Synthetic methods for all classes of glucuronides are reviewed and updated, together with advances in the enzymatic synthesis of glucuronides and methods for their detection. Finally we discuss the biological reactivity of glucuronides where known, including the important morphine-6-glucuronide. A lively debate has continued for several years on whether O-acyl glucuronide metabolites of carboxylic acids are toxic, affecting both the safety assessment of well-used drugs and new drug development programmes. We summarise the current understanding, together with other known examples of interaction between glucuronides and macromolecules.

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Section: Biogenesis: Udp-glucuronosyl Transferases (Ugts)mentioning

confidence: 99%

Section: Oxidation Of Glucosidesmentioning

confidence: 99%

Glucuronides from metabolites to medicines: a survey of the in vivo generation, chemical synthesis and properties of glucuronides

Stachulski

Meng

2013

Nat. Prod. Rep.

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“…2,4-dichlorophenol is an important organic intermediates, and is widely used in the production of pesticide, medicine and other industries. [1] 2,4-dichlorophenol is mostly produced by phenol after chlorination [2] . The purity of coarse product of 2,4-dichlorophenol is close to 90%, the impurities mainly contain 2,3-dichlorophenol, 2,6-dichlorophenol and 2,4,6-trichlorophenol.…”

Section: Introductionmentioning

confidence: 99%

Solid-Liquid Equilibria for Binary Mixture of Dichlorophenols

Wang

Huang

et al. 2014

AMR

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Differential Scanning Calorimeter (DSC) was used to investigate the thermal properties of 2,4-dichlorophenol+2,6-dichlorophenol and 2,4-dichlorophenol+2,3-dichlorophenol binary systems. The experimental results showed that The phase diagram of 2,4-dichlorophenol+2,6-dichlorophenol system was a simple eutectic type with the eutectic point at 294.99 K and 0.6200 mole fraction of 2,4dichlorophenol; The phase diagram of 2,4dichlorophenol+2,3dichlorophenol system was a simple eutectic type with the eutectic point at 291.86 K and 0.5834 mole fraction of 2,4dichlorophenol. Furthermore, the activity coefficients of components in mixtures of 2,4dichlorophenol+2,6dichlorophenol and2,4dichlorophenol+ 2,3dichlorophenol binary systems have been correlated by the Wilson model, respectively.

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Functional expression of uridine diphospho glucuronosyltransferases in fission yeast

Buchheit¹

2011

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Synthesis of the β-D-Glucuronides of 2,3-, 3,4-, and 2,6-Dichlorophenol

Cited by 3 publications

References 9 publications

Glucuronides from metabolites to medicines: a survey of the in vivo generation, chemical synthesis and properties of glucuronides

Glucuronides from metabolites to medicines: a survey of the in vivo generation, chemical synthesis and properties of glucuronides

Solid-Liquid Equilibria for Binary Mixture of Dichlorophenols

Functional expression of uridine diphospho glucuronosyltransferases in fission yeast

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