Papers by Andrew Mulvaney
Tetrahedron Asymmetry, 2007
Journal of the Chemical Society, Perkin Transactions 1, 2000
Treatment of a range of N-benzyl tertiary amines with aqueous ceric ammonium nitrate results in N... more Treatment of a range of N-benzyl tertiary amines with aqueous ceric ammonium nitrate results in N-debenzylation to afford the corresponding secondary amine. Chemoselective mono-N-debenzylation of N-benzyl tertiary amines is shown to occur in the presence of N-benzyl ...
ChemInform, 2000
Chemoselective Oxidative Debenzylation of Tertiary N-Benzyl Amines.
Tetrahedron: Asymmetry, 2007
The parallel asymmetric synthesis of an array of 30 β-amino acids of high enantiomeric purity usi... more The parallel asymmetric synthesis of an array of 30 β-amino acids of high enantiomeric purity using the conjugate addition of homochiral lithium N-benzyl-N-(α-methylbenzyl)amide as the key step is accomplished. The experimental simplicity and highly practical nature of the protocol is demonstrated by the efficient parallel conversion of 15 α,β-unsaturated esters to both enantiomeric series of the corresponding β-amino acids in
Organic & Biomolecular Chemistry, 2008
A N-benzyl-4-amino-2,2-dimethylbutanoic acid-based system has been developed as a new oxidatively... more A N-benzyl-4-amino-2,2-dimethylbutanoic acid-based system has been developed as a new oxidatively activated safety catch linker for reaction monitoring and optimisation on solid support. The CAN promoted oxidative debenzylation of the tertiary N-benzylamine moiety, followed by concomitant cyclisation and release of alcohols and amines has been demonstrated both in solution phase model studies and on the solid phase. The linker system has been applied to the solid phase synthesis of a collection of phenol derivatives, and to the demonstration of the attachment and release of a chiral auxiliary from a solid support.
Nachrichten aus der Chemie, 2000
Journal of Organometallic Chemistry, 1996
It has been found that dibutyltin dilaurate and dibutyltin dibutanethiolate are almost equally ef... more It has been found that dibutyltin dilaurate and dibutyltin dibutanethiolate are almost equally effective as catalysts in the formation of a urethane from phenyl isocyanate and butanol, and that the catalytic activity of both compounds is inhibited by thiols. These results are consistent with a mechanism which involves the N-coordination of the isocyanate with a tin alkoxide that is formed
Journal of Organometallic Chemistry, 1996
Drug Discovery Today, 2000
C ardiac cation channels have been widely touted as the target of choice for the treatment of car... more C ardiac cation channels have been widely touted as the target of choice for the treatment of cardiac arrhythmia. However, drugs that target these channels have improved the survival of cardiac patients only moderately, highlighting a need for fresh approaches to antiarrhythmic therapy 1,2 . New targets, including Cl Ϫ channels, have thus been identified as potentially important sites of action for future antiarrhythmic agents 3-8 . This article therefore outlines the molecular and biophysical properties of cardiac Cl Ϫ channels and their putative physiological and pathological roles. It then describes ways of identifying novel Cl Ϫ channel modulators.
Chemical Communications, 2000
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Bioorganic & Medicinal Chemistry Letters, 2003
The synthesis and inhibitory activity of a series of 5-substituted-(1,1-dioxo-2,3-dihydro-1H-1l 6... more The synthesis and inhibitory activity of a series of 5-substituted-(1,1-dioxo-2,3-dihydro-1H-1l 6 -benzo[e][1,2]thiazin-4ylidene)-thiazolidine-2,4-dione derivatives as competitive inhibitors of recombinant bacterial arylamine-N-acetyltransferases (NATs) are described. The most potent NAT inhibitors are those that contain planar hydrophobic substituents on the sultam nitrogen. #
Bioorganic & Medicinal Chemistry, 2003
Arylamine N-acetyltransferases (NATs) catalyse the acetylation of arylamine, arylhydrazine and ar... more Arylamine N-acetyltransferases (NATs) catalyse the acetylation of arylamine, arylhydrazine and arylhydroxylamine substrates by acetyl Coenzyme A. NAT has been discovered in a wide range of eukaryotic and prokaryotic species. Although prokaryotic NATs have been implicated in xenobiotic metabolism, to date no endogenous role has been identified for the arylamine N-acetyl transfer reaction in prokaryotes. Investigating the substrate specificity of these enzymes is one approach to determining a possible endogenous role for prokaryotic NATs. We describe an accurate and efficient assay for NAT activity that is suitable for high-throughput screening of potential NAT ligands. This assay has been utilised to identify novel substrates for pure NAT from Salmonella typhimurium and Mycobacterium smegmatis which show a relationship between the lipophilicity of the arylamine and its activity as a substrate. The lipophilic structure/activity relationship observed is proposed to depend on the topology of the active site using docking studies of the crystal structures of these NAT isoenzymes. The evidence suggests an endogenous role of NAT in the protection of bacteria from aromatic and lipophilic toxins. #
New anti-tubercular drugs and drug targets are urgently needed to reduce the time for treatment a... more New anti-tubercular drugs and drug targets are urgently needed to reduce the time for treatment and also to identify agents that will be effective against Mycobacterium tuberculosis persisting intracellularly. Mycobacteria have a unique cell wall. Deletion of the gene for arylamine N-acetyltransferase (NAT) decreases mycobacterial cell wall lipids, particularly the distinctive mycolates, and also increases antibiotic susceptibility and killing within macrophage of Mycobacterium bovis BCG. The nat gene and its associated gene cluster are almost identical in sequence in M. bovis BCG and M. tuberculosis. The gene cluster is essential for intracellular survival of mycobacteria. We have therefore used pure NAT protein for high-throughput screening to identify several classes of small molecules that inhibit NAT activity. Here, we
Tetrahedron: Asymmetry, Jan 1, 1996
Condensation of [3-hydroxy alcohols with ferrocenyl chloride gave the corresponding amides which ... more Condensation of [3-hydroxy alcohols with ferrocenyl chloride gave the corresponding amides which were dehydrated to give ferrocenyl oxazolines in good overall yield. Subsequent lithiation with n-BuLl in the presence of TMEDA and addition of PPh2C1 led to the isolation of (S)-(s)-ipr-phosferrox and (S)-(S)-Me-phosferrox ligands 1 and 2. Their corresponding diastereoisomers, (S)-(R)JPr-phosferrox and (S)-(R)-Me-phosferrox 3 and 4
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Papers by Andrew Mulvaney