- A convenient new synthesis of quaternary ammonium glucuronides of drug molecules
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N-Glucuronides, of various structural types, are frequently encountered as drug metabolites. Efficient chemical synthesis of these compounds, both as analytical standards and for toxicological investigation, is therefore an important goal. Earlier syntheses of N+- glucuronides of aliphatic tertiary amine drugs involved direct reaction of the drug molecule with a bromosugar, but yields were generally low and of poor reproducibility, with many by-products. In addition the final products were often of low stability, hindering effective isolation and purification. We now report that a stable, readily prepared glucuronic acid hemiacetal is a reliable precursor for metabolites of this type and give three pharmaceutically relevant examples. We report further on the stability of the final metabolites and the conditions required for their isolation and purification.
- Iddon, Lisa,Bragg, Ryan A.,Harding, John R.,Stachulski, Andrew V.
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scheme or table
p. 537 - 541
(2010/03/03)
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- Cholinergic enhancers with improved blood-brain barrier permeability for the treatment of diseases accompanied by cognitive impairment
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The present invention refers to compounds that, in addition to enhancing the sensitivity to acetylcholine
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Page/Page column 27-28
(2008/06/13)
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- Convenient syntheses of deoxypyranose sugars from glucuronolactone
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One of the characteristic reactions of glucuronic acid derivatives is the base-catalysed elimination of a 4-(substituted) hydroxy group to generate a Δ4,5 pyranose. Following hydrogenation, proceeding mainly from the α-face provided the anomeri
- Stanford (nee Sinnott), Deborah,Stachulski, Andrew V.
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p. 2361 - 2364
(2007/10/03)
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- A simple synthesis of morphine-3,6-di-β-D-glucuronide
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A convenient two-step synthesis of morphine-3,6-di-β-D-glucuronide in fair yield from morphine and methyl 2,3,4-tri-O-isobutyryl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate is reported. (C) 2000 Elsevier Science Ltd.
- Brown, Richard T,Carter, Neil E,Mayalarp, Stephen P,Scheinmann, Feodor
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p. 7591 - 7594
(2007/10/03)
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- Synthesis of a Morphine-6-Glucuronide Hapten, N-(4-Aminobutyl)normorphine-6-Glucuronide, and Related Haptens
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For use as a hapten in the radioimmunoassay of morphine-6-glucuronide (2) (M6G), N-(4-aminobutyl)normorphine-6-glucuronide 12 has been prepared, together with related haptens, using the imidate coupling method developed for synthesis of M6G; a rebuttal of recent critical comments on our synthesis of M6G is included.
- Brown, Richard T.,Carter, Neil E.,Lumbard, Keith W.,Scheinmann, Feodor
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p. 8661 - 8664
(2007/10/02)
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