Methyl (Cortison-21-yl 2,3,4-tri-O-acetyl-β-D-glucosid)uronate<sup>1</sup>

Zorbach, W. Werner; Valiaveedan, George D.

doi:10.1021/jo01031a517

Cited by 13 publications

(4 citation statements)

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“…above. Phenol (AE)-83 gave a very good yield (67%) of conjugate on reaction with 8 and BF 3 $OEt 2 ; 42,43 deprotection gave an in vivo metabolite of naproxen.…”

Section: O-alkylmentioning

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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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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“…above. Phenol (AE)-83 gave a very good yield (67%) of conjugate on reaction with 8 and BF 3 $OEt 2 ; 42,43 deprotection gave an in vivo metabolite of naproxen.…”

Section: O-alkylmentioning

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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“…Glycosylation of 10a was examined by use of glycosyl donors, such as methyl 2,3,4-tri-O-acetyl-(11a) (34) and 2,3,4-tri-O-benzoyl-α-D-glucopyranosyluronate bromide (11b) (35), in the presence of an activator (Figure 3). Treatment of 10a with 3.0 mol equiv.…”

Section: Resultsmentioning

confidence: 99%

First Synthesis of a Natural Neopterin Glycoside: 3'-O-(β-D-Glucopyranosyluronic acid)neopterin

et al. 2010

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“…143–144 °C, lit. [ 43 ] 146–148 °C, [ 43 ] [α]

: = +119.3 (c 1.00, CHCl 3 ), lit [ 43 ]. +114.0 (c 1.31, CHCl 3 ).…”

Section: Methodsmentioning

confidence: 99%

Benzoylated Uronic Acid Building Blocks and Synthesis of N-Uronate Conjugates of Lamotrigine

et al. 2012

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A chemoenzymatic approach towards benzoylated uronic acid building blocks has been investigated starting with benzoylated hexapyranosides using regioselective C-6 enzymatic hydrolysis as the key step. Two of the building blocks were reacted with the antiepileptic drug lamotrigine. Glucuronidation of lamotrigine using methyl (2,3,4-tri-O-benzoyl-α-d-glycopyranosyl bromide)uronate proceeded to give the N2-conjugate. However, lamotrigine-N2-glucuronide was most efficiently synthesised from methyl (2,3,4-tri-O-acetyl-α-d-glucopyranosyl bromide)uronate. Employing nitromethane as solvent with CdCO3 as a base lamotrigine-N2 glucuronide was prepared in a high yield (41%). Also methyl (2,3-di-O-benzoyl-4-deoxy-4-fluoro-α-d-glucosyl bromide)uronate underwent N-glucuronidation, but the product was unstable, eliminating hydrogen fluoride to give the corresponding enoate conjugate.

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Methyl (Cortison-21-yl 2,3,4-tri-O-acetyl-β-D-glucosid)uronate¹

Cited by 13 publications

References 1 publication

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

First Synthesis of a Natural Neopterin Glycoside: 3'-O-(β-D-Glucopyranosyluronic acid)neopterin

Benzoylated Uronic Acid Building Blocks and Synthesis of N-Uronate Conjugates of Lamotrigine

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Methyl (Cortison-21-yl 2,3,4-tri-O-acetyl-β-D-glucosid)uronate1

Cited by 13 publications

References 1 publication

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

First Synthesis of a Natural Neopterin Glycoside: 3'-O-(β-D-Glucopyranosyluronic acid)neopterin

Benzoylated Uronic Acid Building Blocks and Synthesis of N-Uronate Conjugates of Lamotrigine

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Methyl (Cortison-21-yl 2,3,4-tri-O-acetyl-β-D-glucosid)uronate¹