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Critical Care Medicine Dec 2006
Topics: Chemical Warfare; Cholinesterase Reactivators; Humans; Meta-Analysis as Topic; Organophosphate Poisoning; Oximes; Sarin
PubMed: 17130717
DOI: 10.1097/01.CCM.0000248912.59563.B9 -
Acta Crystallographica. Section C,... Jan 20011-Methylindole-3-carboxaldehyde oxime, C10H10N2O, (I), and (E)-5-methoxy-1-methylindole-3-carboxaldehyde oxime, C11H12N2O2, (II), were examined structurally to ascertain...
1-Methylindole-3-carboxaldehyde oxime, C10H10N2O, (I), and (E)-5-methoxy-1-methylindole-3-carboxaldehyde oxime, C11H12N2O2, (II), were examined structurally to ascertain the geometry of the hydroxyimino function relative to the indole core. Oxime (I) exhibits cis geometry and there are two molecules in the asymmetric unit. In contrast, oxime (II) exhibits trans geometry and has four molecules in the asymmetric unit, with the geometry of the 5-methoxy group in one molecule differing from that in the other three. Both crystal structures are maintained by hydrogen bonding with no pi-stacking of the indole moiety present.
Topics: Crystallography, X-Ray; Indoles; Models, Molecular; Molecular Conformation; Oximes
PubMed: 11173398
DOI: 10.1107/s0108270100005795 -
Photochemistry and Photobiology Jul 2022In this work, free radical photopolymerization (FRP) kinetics for series of different phenylamine oxime ester structures (DMA-P, DEA-P, DMA-M, TP-2P, TP-2M and TP-3M)...
Effect of the Steric Hindrance and Branched Substituents on Visible Phenylamine Oxime Ester Photoinitiators: Photopolymerization Kinetics Investigation through Photo-DSC Experiments.
In this work, free radical photopolymerization (FRP) kinetics for series of different phenylamine oxime ester structures (DMA-P, DEA-P, DMA-M, TP-2P, TP-2M and TP-3M) was investigated. Steric hindrance and branched substituents were prepared to realize the corresponding electronic and photopolymerization effects. The photophysical, electrochemical, thermal properties and radical concentration were investigated by UV-visible spectroscopy, cyclic voltammetry (CV), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and electron paramagnetic resonance (EPR). Furthermore, the structure-reactivity relationships were also studied in detail through photo-DSC experiment. We demonstrate that the introduction of alkyl chains and/or numbers of oxime esters affects significantly the photoreactivity. Under the same weight ratio of formulation and irradiated condition, TP-3M containing three oxime esters in its structure and methyl group in the periphery exhibits the highest double-bond conversion efficiency. TP-3M-based formulation also shows a wide operation window under different contents and light intensities. Importantly, the photoreactivity of the TP-3M-based system was found to be better than the commercial photoinitiator (OXE-01) under LED@405 nm at a low concentration. This work could provide some significance to the design of oxime esters with enhanced photoreactivity.
Topics: Aniline Compounds; Calorimetry, Differential Scanning; Esters; Light; Oximes
PubMed: 34674274
DOI: 10.1111/php.13545 -
ChemMedChem Dec 2020The radiosynthesis, as well as the in vivo and ex vivo biodistribution of the C radiolabelled 3-(4,5-diphenyl-1,3-oxazol-2-yl)propanal oxime (6, [ C]SZV 1287) are...
The radiosynthesis, as well as the in vivo and ex vivo biodistribution of the C radiolabelled 3-(4,5-diphenyl-1,3-oxazol-2-yl)propanal oxime (6, [ C]SZV 1287) are reported. SZV 1287 is a novel semicarbazide-sensitive amine oxidase (SSAO) inhibitor and a promising candidate to be a novel analgesic for the treatment of neuropathic pain. Its radiolabelling was developed via a four-step radiosynthesis which started from the reaction of a Grignard reagent with [ C]CO to produce [ C]oxaprozin (3). In the next step this carboxylic acid 3 was directly reduced to yield the corresponding aldehyde, which was then converted into the oxime. [ C]SZV 1287 was administered to male NMRI mice. The animals were examined with dynamic PET/MR imaging for 90 minutes. Biodistribution studies were performed at 10, 30, 60 and 120 minutes post injection. The accumulation of the labelled compound was observed in the brain of the animals. The main excretion pathway was found to be through the liver and intestines. These studies provide preliminary information for pharmacokinetic characterization of the SZV 1287.
Topics: Animals; Carbon Radioisotopes; Male; Mice; Oxazoles; Oximes; Positron-Emission Tomography; Radiopharmaceuticals
PubMed: 32935925
DOI: 10.1002/cmdc.202000389 -
Journal of Pharmaceutical Sciences Jul 1968
Topics: Escherichia coli; Flavoring Agents; Oximes
PubMed: 4873853
DOI: 10.1002/jps.2600570739 -
ChemMedChem Aug 2007The synthesis, in vitro antifungal activity, and molecular docking experiments of some oxime and oxime ether derivatives of azole 1,4-benzothiazine are reported herein,...
The synthesis, in vitro antifungal activity, and molecular docking experiments of some oxime and oxime ether derivatives of azole 1,4-benzothiazine are reported herein, with the aim of evaluating the influence of a partially constrained scaffold that is structurally related to Oxiconazole and bearing the 1,4-benzothiazine moiety, on the inhibition of Candida albicans CYP51.
Topics: Antifungal Agents; Candida albicans; Ethers; Imidazoles; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Oximes; Structure-Activity Relationship; Thiazines
PubMed: 17541993
DOI: 10.1002/cmdc.200700066 -
Journal of Agricultural and Food... Jul 2016A total of 20 esters of fraxinellone C4/10-oxime were synthesized and determined by melting points, optical rotation, infrared spectra, proton nuclear magnetic resonance...
A total of 20 esters of fraxinellone C4/10-oxime were synthesized and determined by melting points, optical rotation, infrared spectra, proton nuclear magnetic resonance spectra, and high-resolution mass spectrometry spectra. Two steric configurations of compounds 7i and 8i were unambiguously confirmed by X-ray crystallography. Additionally, their pesticidal activities were assessed on two typical lepidopteran pests, Mythimna separata Walker and Plutella xylostella Linnaeus. Generally, all compounds exhibited less potent oral toxicity than toosendanin against third-instar larvae of P. xylostella. However, all compounds showed the growth inhibitory property against early third-instar larvae of M. separata. Notably, compounds 7m, 8b, 8k, 9, and 11 displayed more potent pesticidal activity than toosendanin. This demonstrated that introducing the C-4 carbonyl or oxime group on fraxinellone resulted in more promising derivatives than those bearing a C-10 carbonyl or oxime substituent.
Topics: Animals; Benzofurans; Crystallography, X-Ray; Esters; Insecticides; Larva; Molecular Structure; Moths; Oximes
PubMed: 27338830
DOI: 10.1021/acs.jafc.6b01995 -
The Journal of Biological Chemistry Mar 2020Organophosphate (OP) intoxications from nerve agent and OP pesticide exposures are managed with pyridinium aldoxime-based therapies whose success rates are currently...
Organophosphate (OP) intoxications from nerve agent and OP pesticide exposures are managed with pyridinium aldoxime-based therapies whose success rates are currently limited. The pyridinium cation hampers uptake of OPs into the central nervous system (CNS). Furthermore, it frequently binds to aromatic residues of OP-inhibited acetylcholinesterase (AChE) in orientations that are nonproductive for AChE reactivation, and the structural diversity of OPs impedes efficient reactivation. Improvements of OP antidotes need to include much better access of AChE reactivators to the CNS and optimized orientation of the antidotes' nucleophile within the AChE active-center gorge. On the basis of X-ray structures of a CNS-penetrating reactivator, monoxime RS194B, reversibly bound to native and venomous agent X (VX)-inhibited human AChE, here we created seven uncharged acetamido bis-oximes as candidate antidotes. Both oxime groups in these bis-oximes were attached to the same central, saturated heterocyclic core. Diverse protonation of the heterocyclic amines and oxime groups of the bis-oximes resulted in equilibration among up to 16 distinct ionization forms, including uncharged forms capable of diffusing into the CNS and multiple zwitterionic forms optimal for reactivation reactions. Conformationally diverse zwitterions that could act as structural antidote variants significantly improved reactivation of diverse OP-human AChE conjugates. Oxime group reorientation of one of the bis-oximes, forcing it to point into the active center for reactivation, was confirmed by X-ray structural analysis. Our findings provide detailed structure-activity properties of several CNS-directed, uncharged aliphatic bis-oximes holding promise for use as protonation-dependent, conformationally adaptive, "smart" accelerated antidotes against OP toxicity.
Topics: Acetamides; Acetylcholinesterase; Antidotes; Central Nervous System; Cholinesterase Inhibitors; Cholinesterase Reactivators; Crystallography, X-Ray; Humans; Kinetics; Organophosphates; Organophosphorus Compounds; Oximes; Protein Conformation; Structure-Activity Relationship
PubMed: 32019865
DOI: 10.1074/jbc.RA119.012400 -
Pest Management Science Nov 2020In order to discover natural-product-based pesticidal candidates, a series of coumarin-like derivatives containing oxime ester fragments at the C-8 position were...
BACKGROUND
In order to discover natural-product-based pesticidal candidates, a series of coumarin-like derivatives containing oxime ester fragments at the C-8 position were prepared by structural modification of osthole, a natural plant product isolated from Cnidium monnieri. Their pesticidal activities were evaluated against two typically fruit trees/crop-threatening agricultural pests, Mythimna separata Walker and Tetranychus cinnabarinus Boisduval.
RESULTS
Osthole was regioselectively oxidized by selenium dioxide to give the E-isomer, (2'E)-3'-formaldehydylosthole (2). Four key steric structures of 2, (2'E, 4'E)-(o-chloropyrid-3-ylcarbonyl)oximinylosthole (4o), (2'E, 4'E)-(styrylcarbonyl)oximinylosthole (4t), and (2'E, 4'E)-(acetyl)oximinylosthole (4w) were undoubtedly confirmed by X-ray crystallography. Against T. cinnabarinus, it is noteworthy that (2'E, 4'E)-(p-chlorophenylcarbonyl)oximinylosthole (4c) exhibited over three-fold more potent acaricidal activity of the precursor osthole, with especially good control efficiency observed in the glasshouse. Against M. separata, compounds 4c and (2'E, 4'E)-(p-nitrophenylcarbonyl)oximinylosthole (4f) showed the most pronounced growth inhibitory activity. The relationships between their structures and agricultural activities also were studied.
CONCLUSION
These results demonstrate that compound 4c could be further structurally modified as pesticidal agents. It will lay the foundation for future application of osthole derivatives as pesticides. © 2020 Society of Chemical Industry.
Topics: Animals; Cnidium; Coumarins; Molecular Structure; Oximes
PubMed: 32815273
DOI: 10.1002/ps.6056 -
Bioconjugate Chemistry Apr 2018The reaction of unprotected carbohydrates with aminooxy reagents to provide oximes is a key method for the construction of glycoconjugates. Aniline and derivatives serve...
The reaction of unprotected carbohydrates with aminooxy reagents to provide oximes is a key method for the construction of glycoconjugates. Aniline and derivatives serve as organocatalysts for the formation of oximes from simple aldehydes, and we have previously reported that aniline also catalyzes the formation of oximes from the more complex aldehydes, carbohydrates. Here, we present a comprehensive study of the effect of aniline analogues on the formation of carbohydrate oximes and related glycoconjugates depending on organocatalyst structure, pH, nucleophile, and carbohydrate, covering more than 150 different reaction conditions. The observed superiority of the 1,4-diaminobenzene (PDA) catalyst at neutral pH is rationalized by NMR analyses and DFT studies of reaction intermediates. Carbohydrate oxime formation at pH 7 is demonstrated by the formation of a bioactive glycoconjugate from a labile, decorated octasaccharide originating from exopolysaccharides of the soil bacterium Mesorhizobium loti. This study of glycoconjugate formation includes the first direct comparison of aniline-catalyzed reaction rates and equilibrium constants for different classes of nucleophiles, including primary oxyamines, secondary N-alkyl oxyamines, as well as aryl and arylsulfonyl hydrazides. We identified 1,4-diaminobenzene as a superior catalyst for the construction of oxime-linked glycoconjugates under mild conditions.
Topics: Catalysis; Glycoconjugates; Hydrogen-Ion Concentration; Magnetic Resonance Spectroscopy; Mesorhizobium; Oximes; Phenylenediamines; Polysaccharides, Bacterial
PubMed: 29437382
DOI: 10.1021/acs.bioconjchem.8b00019