Although erythromycin A contains five hydroxyl groups, regioselective methylation at the C-6 hydroxyl group was achieved to the extent of 90%when a 9-0-substituted erythromycin A 9-oxime was employedas substrate. The methylation and its selectivity are dependent on an O-protecting group at the 9-oxime, solvent, base, and methylating reagent. In particular, the use ofa polar aprotic solvent is i...

A direct strategy to obtain N-acyl amino acid oxime esters has been developed through the dynamic kinetic resolution of azlactones with oximes. In the presence of a chiral bisguanidinium salt catalyst, a variety of chiral N-acyl amino acid oxime esters were generated in excellent enantiomeric excesses (up to 97%) and high yields (up to 99%). The active oxime esters could be used in dipeptide sy...

Key words photocatalysis - thioxanthones amino acids oxime esters

The synthesis of a set of 1-aryl-2-aryl(3-pyridyl)ethanones 1-5 and the corresponding ketoximes 6-9 is reported. Structural studies of oximes 6, 7 and 9 were performed in solution using (1)H-NMR and in the solid state by X-ray crystallography, providing evidence of H-bonding networks. The crystal packing was controlled by homomeric intermolecular oxime...oxime H-bond interactions for 6 and coop...

Although the blood flow tracer hexamethylpropyleneamine oxime is now widely used for cerebral blood flow mapping using single-photon emission computed tomography, its uptake into acutely ischemic brain has not been well studied. We performed a double-label autoradiographic study in which 99mTc-hexamethylpropyleneamine oxime uptake was compared with [14C]iodoantipyrine-derived cerebral blood flo...

In the present study, Y-tube olfactometric assays demonstrated that headspace volatile extracts collected from leaf miner-damaged, or artificially damaged, bean plants were more attractive to naive females of the parasitoid insect Opius dissitus than those collected from healthy plants. Headspace extracts from both Liriomyza huidobrensis and Liriomyza sativae second-instar larvae-damaged beans ...

Although the blood flow tracer hexamethylpropyleneamine oxime is now widely used for cerebral blood flow mapping using single-photon emission computed tomography, its uptake into acutely ischemic brain has not been well studied. We performed a double-label autoradiographic study in which "Tc-hexamethylpropyleneamine oxime uptake was compared with [C]iodoantipyrine-derived cerebral blood flow 0....

The ability of two newly developed oximes (K305, K307) to protect tabun-poisoned rats from tabun-induced inhibition of brain acetylcholinesterase, acute neurotoxic signs and symptoms and brain damage was compared with that of the oxime K203 and trimedoxime. The reactivating and neuroprotective effects of the oximes studied combined with atropine on rats poisoned with tabun at a sublethal dose w...

This study compared the ability of nine oximes (HI-6, HLö7, MMB-4, TMB-4, carboxime, ICD585, ICD692, ICD3805, and 2-PAM) to reactivate in vivo cholinesterase (ChE) in blood, brain, and peripheral tissues in guinea pigs intoxicated by one of four organophosphorus nerve agents. Two bis-pyridinium compounds without an oxime group, SAD128 and ICD4157, served as non-oxime controls. Animals were inje...

The highly toxic nature of tabun has been known for many years, but there are still serious limitations to antidotal therapy. In this study, we used rats as an experimental model to evaluate the efficiency of bispyridinium para-oxime K203 as therapy against tabun poisoning as well as to examine if induction of oxidative stress is linked to organophosphate toxicity. K203 showed high potency in c...