The title compound, C(11)H(13)NO(4), contains a nitrone group, C=N-O-R, the geometry of which shows a Z configuration with near planarity (r.m.s. deviation = 0.0787 Å) around the C=N double bond. An intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal packing, mol-ecules are linked into R(2) (2)(12) dimers and R(2) (2)(14) rings via C-H⋯O inter-molecular hydrogen bonds.

A new cyclic nitrone spin trap, [4-(3',3'-dibutyl-2'-oxy-3'H-isoindol-5'-yloxy)butyl]triphenylphosphonium bromide (MitoSpin), bearing a lipophilic cation has been prepared by a route that involves a novel Parham-type lithiation-cyclization of an isocyanate to give the isoindolinone core. MitoSpin accumulates in a membrane potential dependent way in energized mitochondria and its oxidation could...

The title compound, C(22)H(32)N(2)O(2)S, was obtained by dehydroxy-lation and deacetyl-ation of 4-{(1S,2S)-2-(benzylhydroxy-amino)-3-methyl-1-[(S)-2-methyl-propane-2-sulfinylamino]but-yl}phenyl acetate, which was derived from reductive crosslinking of nitrone with N-tert-butane-sulfinyl-imine. The crystal structure shows that the mol-ecules are linked by O-H⋯O hydrogen bonds.

The stereoselective synthesis of penmacric acid, an optically active C-4 substituted pyroglutamic acid, has been efficiently achieved through an unusual 11-step sequence starting from simple N-triisopropylsilylpyrrole. The key-steps are the initial addition of the pyrrole nucleus onto a chiral nitrone and the obtention of the pyroglutamic acid moiety by reductive hydrogenation of the pyrrole fo...

The inactivation of cytochrome P450 enzymes by cyclopropylamines has been attributed to a mechanism involving initial one-electron oxidation at nitrogen followed by scission of the cyclopropane ring leading to covalent modification of the enzyme. Herein, we report that in liver microsomes N-cyclopropylbenzylamine (1) and related compounds inactivate P450 to a large extent via formation of metab...

Preparation of a series of terminally and internally substituted delta-alkenyl and delta-alkynyl esters 6, 7 and 9, potential precursors to oxazin-2-one nitrones, has been attempted. Condensation between pyruvic or benzoylformic acid and the appropriate alcohol proceeded smoothly in some cases whilst allylic transposition was a major feature in other cases--most especially during reactions with...

Apocynin, a potent inhibitor of NADPH-oxidase, was widely studied for activities in diseases such as inflammation-mediated disorders, asthma and cardiovascular diseases. In our recent study, a novel nitrone derivative of apocynin, AN-1, demonstrated potent inhibition to oxidative injury and to high expression of gp91(phox) subunit of NADPH-oxidase induced by tert-butyl hydroperoxide (t-BHP) in ...

Hydroxyl free radical production seems to play an important role in the pathogenesis of Parkinson's disease. In the present study, we investigated the dopamine agonists pramipexole and pergolide as well as the nitrone compound S-PBN (N-tert-butyl-alpha-(2-sulfophenyl)nitrone) to reduce hydroxyl radical formation. Microdialysis experiments were carried out in non-anaesthetized Wistar rats. Salic...