Relevant bibliographies by topics / Hydroxylamine derivatives

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Academic literature on the topic 'Hydroxylamine derivatives'

Author: Grafiati
Published: 18 May 2024

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Journal articles on the topic "Hydroxylamine derivatives"

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Reissig, Hans-Ulrich, and Reinhold Zimmer. "Cyclizations of Alkoxyallenes: Mechanisms, Intermediates, ­Products – A Personal Account on Solved and Unsolved Problems with Unique Allene Building Blocks." Synthesis 49, no. 15 (June 6, 2017): 3291–302. http://dx.doi.org/10.1055/s-0036-1588846.

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The additions of lithiated alkoxyallenes to electrophiles, such as carbonyl compounds, thioketones, imines, and nitrones, provide the expected primary addition products. These alkoxyallene intermediates undergo ring-closure reactions under quite different conditions. Whereas allenyl hydroxylamine derivatives spontaneously cyclize to 1,2-oxazine derivatives, the related allenyl amines, thiols, and alcohols require, with distinct exceptions, promotion by acids, base, silver(I), or gold(I). The different mechanisms of these processes are discussed in this account. The serendipitous discovery of a novel three-component reaction of lithiated alkoxyallenes, nitriles, and carboxylic acids followed by a cyclization to pyridine derivatives is also reported and the mechanism involved is illustrated. This account also compiles exemplary examples of natural products and other compounds prepared by subsequent reactions of alkoxyallene-based cyclization products, but the fascinating ring-closing event of the allenyl intermediates is the main focus of this report.1 Introduction2 Cyclizations of Allenyl Hydroxylamines to 1,2-Oxazine Derivatives3 Cyclizations of Allenyl Amines to Dihydropyrrole Derivatives4 Cyclizations of Allenyl Imines to Pyrroles – Discovery of a New Three-Component Synthesis of Pyridines5 Cyclizations of Allenyl Thiols to Vinylthiiranes and Dihydrothiophene Derivatives6 Cyclizations of Allenyl Alcohols to Dihydrofuran Derivatives7 Conclusions
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2

Rehse, Klaus, and Tawfig Shahrouri. "Hydroxylamine Derivatives." Archiv der Pharmazie 331, no. 11 (November 1998): 365–67. http://dx.doi.org/10.1002/(sici)1521-4184(199811)331:11<365::aid-ardp365>3.0.co;2-n.

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3

Torruellas, Carilyn, Fu-Lian Hsu, and Andrew J. Walz. "Synthesis of N-Pyridyl Hydroxylamines via Copper-Catalyzed Cross-Coupling." Synthesis 51, no. 15 (May 15, 2019): 2891–96. http://dx.doi.org/10.1055/s-0037-1611836.

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N-Pyridyl hydroxylamine derivatives were prepared via copper-catalyzed cross-coupling of orthogonally functionalized hydroxylamines with iodopyridines. Various amino- and hydroxyl-protecting groups were tolerated. A total of 20 examples were synthesized in 28–90% yield.
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Pískala, Alois, Naeem B. Hanna, Milena Masojídková, Pavel Fiedler, and Ivan Votruba. "Synthesis of N4-Amino and N4-Hydroxy Derivatives of 5-Azacytidine. A Facile Rearrangement of the N4-Amino Derivative to 5-(3-β-D-Ribofuranosylureido)-1H-1,2,4-triazole." Collection of Czechoslovak Chemical Communications 69, no. 4 (2004): 905–17. http://dx.doi.org/10.1135/cccc20040905.

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Treatment of methoxyribosyltriazinone 4 with hydrazine in methanol afforded crude 4-hydrazino-1-β-D-ribofuranosyl-1,3,5-triazin-2(1H)-one (N4-amino-5-azacytidine) (2), which rearranged rapidly to isomeric 5-ribosylureidotriazole 6. The rearrangement proceeds easily also in water solutions of 2. Alkaline hydrolysis of 6 gave a mixture of 5-ureidotriazole 7 and 5-aminotriazole 8. Acid hydrolysis of 6 afforded only 7. This compound was also prepared by thermal rearrangement of 5-amino-1-carbamoyltriazole 9 or on reaction of cyano(formyl)guanidine 10 with hydrazine hydrochloride. Treatment of benzoylated methoxyribosyltriazinone 4a with hydrazine in methanol gave only the rearranged product 6a. Reaction of tribenzoylribosyl isocyanate 12 with aminotriazole 8 gave 1-triazolecarboxamidotribenzoylribose 13, which afforded by methanolysis oxazoloribofuranose 14 and aminotriazole 8. Compound 14 was also obtained by methanolysis of blocked ribosylcarbamate 16. Reaction of methoxyribosyltriazinone 4 with hydroxylamine in methanol afforded 4-hydroxylamino-1-β-D-ribofuranosyl-1,3,5-triazin-2(1H)-one (N4-hydroxy-5-azacytidine) (3), which on the action of excess hydroxylamine yielded 1-cyano-1-hydroxy-5-β-D-ribofuranosylisobiuret (19). Treatment of methoxy-1,3,5-triazinone 18 with a solution of hydroxylamine in methanol gave 4-hydroxylamino-1-methyl-1,3,5-triazin-2(1H)-one (N4-hydroxy-1-methyl-5-azacytosine) (17). Heating of cyano(formyl)guanidine 10 with hydroxylamine hydrochloride in water lead to the formation of triuret (21). The mechanisms of the reactions of methoxyribosyltriazinone 4 with hydrazine and hydroxylamine are discussed. Compounds 2, 6 and 19 exhibited no significant antibacterial or cytostatic activity.
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Baldauf, Simon, and Jeffrey Bode. "Synthesis and Evaluation of Cyclic Acetals of Serine Hydroxylamine for Amide-Forming KAHA Ligations." Synthesis 51, no. 05 (January 7, 2019): 1273–83. http://dx.doi.org/10.1055/s-0037-1611635.

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The α-ketoacid–hydroxylamine (KAHA) ligation allows the coupling of unprotected peptide segments. The most widely used variant employs a 5-membered cyclic hydroxylamine that forms a homoserine ester as the primary ligation product. While very effective, monomers that give canonical amino acid residues are in high demand. In order to preserve the stability and reactivity of cyclic hydroxylamines, but form a canonical amino acid residue upon ligation, we sought to prepare cyclic derivatives of serine hydroxylamine. An evaluation of several cyclization strategies led to cyclobutanone ketals as the leading structures. The preparation, stability, and amide-forming ligation of these serine-derived ketals are described.
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Veits, Gesine K., Donald R. Wenz, Leoni I. Palmer, André H. St. Amant, Jason E. Hein, and Javier Read de Alaniz. "Cascade rearrangement of furylcarbinols with hydroxylamines: practical access to densely functionalized cyclopentane derivatives." Organic & Biomolecular Chemistry 13, no. 31 (2015): 8465–69. http://dx.doi.org/10.1039/c5ob00944h.

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The aza-Piancatelli rearrangement with hydroxylamines to 4-aminocyclopentenones is described. Subsequent transformations highlight the versatility of the cyclopentene scaffold and the value of the hydroxylamine in this transformation.
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Spooren, Anita AMG, and Chris TA Evelo. "Only the glutathione dependent antioxidant enzymes are inhibited by haematotoxic hydroxylamines." Human & Experimental Toxicology 17, no. 10 (October 1998): 554–59. http://dx.doi.org/10.1177/096032719801701005.

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Hydroxylamine and some of its derivatives are known to cause oxidative effects both in vitro and in vivo.Inthe current study we investigated the effects of hydroxyla-mines on the enzymatic antioxidant defense system in human erythrocytes. The activity of catalase and super-oxide dismutase was not significantly influenced by any of the hydroxylamines tested. However, the activity of glutathione peroxidase (GPX) and glutathione S-transferase (GST) was strongly inhibited by hydroxylamine and its O-derivatives (O-methyl and O-ethyl hydroxylamine). GPX was also inhibited by two N-derivatives of hydro-xylamine (i.e. N-dimethyl and N, O-dimethyl hydroxyla-mine). This indicates that exposure to hydroxylamines not only changes the cellular oxidation-reduction status but also leads to inhibition of the glutathione dependent antioxidant enzymes. GST as well as GPX have cysteine residues at the active site of the enzymes. Such an accessible thiol group is generally susceptible to formation of protein-mixed disulphides or intramolecular disulphides. If these thiol groups are essential for activity this would be accompanied by an increase or decrease in the enzyme activity. In principle this is also true for glutathione reductase (GR), which in this study was only inhibited by N, O-dimethyl and N-methyl hydroxylamines. However, GR is capable to reduce these disulphides by taking up two electrons, either from its substrate NAPDH or from another reductant. Oxidation of these thiol groups in GR would thus not lead to impairment of GR activity. The fact that NODMH and NMH do decrease the GR activity can therefore only be explained by other modifications. The activity loss of GST and GPX on the other hand, is likely to involve oxidation of critical cysteine residues. The practical consequence of these findings is that the cellular prooxidant state that may arise in erythrocytes exposed to hydroxylamines can be further increased by activity loss of protective enzymes, which may decrease the average life span of the red blood cell.
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Guy, Michelle, Sally Freeman, John Alder, and Simon Brandt. "The Henry reaction: spectroscopic studies of nitrile and hydroxylamine by-products formed during synthesis of psychoactive phenylalkylamines." Open Chemistry 6, no. 4 (December 1, 2008): 526–34. http://dx.doi.org/10.2478/s11532-008-0054-z.

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AbstractA clandestine two-step route to psychoactive racemic phenylalkylamines utilises the Henry reaction. In the first step an aromatic aldehyde reacts with a nitroalkane to give the nitrostyrene intermediate. In the second step the nitrostyrene is reduced to the phenylalkylamine. An impurity profile of both steps was evaluated through the synthesis and analysis of common street derivatives. The formation of nitrile impurities in the nitroaldol reaction and hydroxylamine impurities in the reduction step were shown by NMR spectroscopy and GC-MS. A selection of reducing agents has been used to give the phenylalkylamines, together with variable quantities of the partially reduced hydroxylamine product. GC-MS analysis of the hydroxylamines showed heat-induced disproportionation which led to the detection of the corresponding oximes.
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Hashem, Heba E., and Ahmed M. Abo-Bakr. "Synthesis of Some New 1,2,4-Triazine and 1,2,5-Oxadiazine Derivatives with Antimicrobial Activity." Heteroatom Chemistry 2019 (September 25, 2019): 1–7. http://dx.doi.org/10.1155/2019/2326514.

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1,2,4-Triazine and 1,2,5-oxadiazine derivatives 2–12 were obtained from treated 1,3-oxazolone (1) with phenyl hydrazine or hydroxylamine hydrochloride. Chlorotriazine derivative 3 undergoing condensation reactions with different reagents produced new fused tetrazolo-triazine and triazino-quinazolinone derivatives. 1,2,5-Oxadiazine has been used as a synthon for the fused pyrazolo-oxadiazine derivative. The constitution of the prepared compounds was built up based on microanalytical and spectral data. Some of the new compounds were assessed for their antimicrobial activity.
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Anyun, Zhang, Hu Jingxin, Zhang Xianye, and Wang Fangding. "Hydroxylamine derivatives in Purex Process." Journal of Radioanalytical and Nuclear Chemistry 230, no. 1-2 (April 1998): 235–39. http://dx.doi.org/10.1007/bf02387470.

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Dissertations / Theses on the topic "Hydroxylamine derivatives"

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Eve, Tom S. C. "Biotransformations of hydroxylamine derivatives." Thesis, University of Edinburgh, 2007. http://hdl.handle.net/1842/14813.

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The results presented herein represent a programme focussed towards producing a deracemisation system for hydroxylamines. A number of different avenues have been explored. The use of a number of biocatalytic systems was investigated in an attempt to construct a one-pot system. These included a novel application of monoamine N and laccase enzymes. The enantioselective oxidation of hydroxylamine ethers by MAO-N was a novel discovery. A further development is the engineering of a MAO-N variant which displayed improved catalytic activity for a model hydroxylamine ether substrate compared with the parental enzyme. A second research programme lead to the discovery of the applicability of a laccase:mediator system to the oxidation of hydroxylamines. Investigations into oxime reduction systems with reaction conditions that were complementary to the biocatalytic systems were performed.
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2

Mauger-Chalaye, Hélène. "Réactions des nitrones avec les noyaux indoliques : nouvelles approches synthétiques d'alcaloïdes indoliques bio-actifs." Université Joseph Fourier (Grenoble), 1999. http://www.theses.fr/1999GRE10047.

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Parmi les composes naturels possedant des proprietes antivirales et/ou antitumorales, les alcaloides indoliques font l'objet d'un interet particulier. Afin de former le motif (3-indolyl)methylamine, base structurale de certains de ces derives bio-actifs, nous avons etudie la reactivite des nitrones vis-a-vis des noyaux indoliques. Utilisant 2 modes differents d'activation des nitrones, nous avons pu acceder a deux classes de produits : les n-hydroxylamines indoliques, et les 3,3-diindolylalcanes. Chacune des deux methodologies mises au point a par la suite ete exploitee pour synthetiser d'une part des derives bis-indoliques naturels ou non symetriques, d'autre part des 1,2-diamines indoliques. Ces dernieres sont des precurseurs potentiels des topsentines, des nortopsentines et du discodermindole, composes bio-actifs isoles d'eponges marines et possedant un noyau imidazole ou imidazoline. Nous avons envisage de former ces cycles azotes en condensant les 1,2-diamines obtenues avec un acide indolique convenablement active. Dans le cadre de ce projet, nous avons verifie la faisabilite chimique des strategies envisagees en utilisant le 1,2-diaminoethane comme modele. Un analogue debrome et protege du discodermindole a egalement ete obtenu.
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Books on the topic "Hydroxylamine derivatives"

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Parker, Philip M. The World Market for Organic Derivatives of Hydrazine or Hydroxylamine: A 2007 Global Trade Perspective. ICON Group International, Inc., 2006.

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2

Parker, Philip M. The 2007 Import and Export Market for Organic Derivatives of Hydrazine or Hydroxylamine in India. ICON Group International, Inc., 2006.

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Parker, Philip M. The 2007 Import and Export Market for Organic Derivatives of Hydrazine or Hydroxylamine in China. ICON Group International, Inc., 2006.

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The World Market for Organic Derivatives of Hydrazine or Hydroxylamine: A 2004 Global Trade Perspective. Icon Group International, Inc., 2005.

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Parker, Philip M. The 2007 Import and Export Market for Organic Derivatives of Hydrazine or Hydroxylamine in United States. ICON Group International, Inc., 2006.

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Book chapters on the topic "Hydroxylamine derivatives"

1

Koeber, Karl, Helga Köttelwesch, Dietrich Schneider, Helga Demmer, and Edith Schleitzer-Rust. "Complexes with Derivatives of Hydroxylamine." In Mn Manganese D 5, 211–30. Berlin, Heidelberg: Springer Berlin Heidelberg, 1987. http://dx.doi.org/10.1007/978-3-662-08175-4_6.

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2

Khomutov, A. R., A. G. Gabibov, E. N. Khurs, E. A. Tolosa, A. M. Shuster, E. V. Goryachenkova, and R. M. Khomutov. "Selective Inhibition of PLP-Dependent Enzymes by Hydroxylamine Derivatives." In Biochemistry of Vitamin B6, 317–20. Basel: Birkhäuser Basel, 1987. http://dx.doi.org/10.1007/978-3-0348-9308-4_54.

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Förster, Verena, and Wolfgang Junge. "On the action of hydroxylamine, hydrazine and their derivatives on the water-oxidizing complex." In Current topics in photosynthesis, 195–208. Dordrecht: Springer Netherlands, 1986. http://dx.doi.org/10.1007/978-94-009-4412-1_19.

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4

Sartori, G., and R. Maggi. "From Isocyanates and Hydroxylamine Derivatives." In Four Carbon-Heteroatom Bonds, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-018-00861.

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5

Cordero, F. M., and S. Cicchi. "Condensation of Hydroxylamine." In Three Carbon-Heteroatom Bonds: Amides and Derivatives; Peptides; Lactams, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-022-00369.

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Iesce, M. R., and M. DellaGreca. "Trapping with Hydrazine Derivatives or Hydroxylamine." In Peroxides, Inorganic Esters (RO-X, X=Hal, S, Se, Te, N), 1. Georg Thieme Verlag KG, 2009. http://dx.doi.org/10.1055/sos-sd-038-00318.

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Drabowicz, J., J. Lewkowski, C. V. Stevens, D. Krasowska, and R. Karpowicz. "Reaction of Dialkylhalophosphines with Hydroxylamine ­Derivatives." In Organophosphorus Compounds (incl. RO-P and RN-P), 1. Georg Thieme Verlag KG, 2009. http://dx.doi.org/10.1055/sos-sd-042-00713.

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Ostrowska, K., and A. Kolasa. "Transaminations with Hydroxylamine or Hydrazine Derivatives." In Three Carbon-Heteroatom Bonds: Amides and Derivatives; Peptides; Lactams, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-022-00587.

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Ostrowska, K., and A. Kolasa. "Addition of Hydroxylamine to Nitriles." In Three Carbon-Heteroatom Bonds: Amides and Derivatives; Peptides; Lactams, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-022-00576.

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Ostrowska, K., and A. Kolasa. "Reactions of Imidoyl Chlorides with Hydroxylamine, O-Substituted, or N-Substituted Hydroxylamines." In Three Carbon-Heteroatom Bonds: Amides and Derivatives; Peptides; Lactams, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-022-00580.

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Conference papers on the topic "Hydroxylamine derivatives"

1

Bock, Paul E. "ACTIVE SITE-SELECTIVE LABELING OF THROMBIN WITH FLUORESCENCE PROBES USING THI0ESTER DERIVATIVES OF PEPTIDE-CHL0R0METHYL KETONES." In XIth International Congress on Thrombosis and Haemostasis. Schattauer GmbH, 1987. http://dx.doi.org/10.1055/s-0038-1644664.

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Active site-directed inactivation of a serine protease with a thioester derivative of a peptide-chloromethyl ketone followed by reaction of the unique thiol group generatedin the presence of hydroxylamine with a fluorophore-iodoacetamide hasbeen investigated as a new method for covalent incorporation of extrinsic fluorescence probes into the active sites of blood coagulation proteases. The specificity of labeling by this method was evaluated by quantitation of the reactions between human thrombin, acetylthioacetyl-D-Phe-Pro-ArgCH2Cl (ATA-FPRCK) and 5-iodoacetamidofluorescein(IAF).ATA-FPRCK was synthesized by reaction of FPRCK with succinimidylacetylthioacetate and purified by chromatography on SP-Sephadex and Sephadex G10. Titrations of the loss of thrombin chromogenic substrate activity with ATA-FPRCK were linear, with end points of 1.1-1.2 mol ATA-FPRCK added/mol active sites, consistent with a reaction stoichiometry of 1 and the ∽90% purity of the compound estimated by reverse-phase HPLC.Inactivation of thrombin wasquantitatively correlated with incorporation of the thioester, with a maximum of 1.04 mol/mol active sites.IAF labeling of ATA-FPR-thrombin inthe presence of 0.1M NH20H yielded a maximu of 0.96 mol IAF incorporated/mol active sites in a reaction accompanied by loss of the thiol group. Incorporation of ATA-FPRCK wasdependent on thefunctional thrombin active site, asdemonstrated by less than 4%thioester or IAF incorporation for the enzyme previously inactivated with FPRCK. I conclude that active site-selective fluorescence labelingcan be achieved by the method described here with the advantage of a wide choice in the properties of theprobe incorporated. In addition, a 2.3-fold difference in fluorescenceintensity was observed for 2,6-ANS derivatives of ATA-FPR-thrombin andATA-D-Phe-Phe-Arg-thrombin, indicating that the spectral properties ofenvironmentally sensitive fluorescence probes are influenced by the structure of the peptide inhibitor.Supported in part by a grant from the American National Red Cross.
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Dwivedi, C., R. Pannell, and V. Gurewich. "FIBRIN ACTIVATABLE UROKINASE (FA-UK): A LATENT FORM OF UK IN URINE RELATED TO A COMPLEX WITH AN INHIBITOR/FIBRIN-BINDING CO-FACTOR OF UK AND POSSIBLY OF PRO-UK." In XIth International Congress on Thrombosis and Haemostasis. Schattauer GmbH, 1987. http://dx.doi.org/10.1055/s-0038-1642905.

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The plasminogen activator activity in urine, expressed in IU, was found to be consistently 2-3 fold higher by fibrin plate assay than against amidolytic substrate (S-2444). Moreover, when the S-2444 assay was preceded by incubation of urine with soluble fibrin, a similar 2-3 fold increase in activity was found. The fibrin effect was dose-dependent and specific for various forms of soluble fibrin but not fibrinogen. The fibrin activatable activity was inhibited by antibodies to UK and was termed FA-UK. About 1/3 of the total UK activity in freshly voided urine was composed of FA-UK. The relative FA-UK content of urine was found to be enhanced by concentration. The FA-UK bound to fibrin/Celite. By gel filtration (S-200) of urine or by zymography, the MW of FA-UK was - 100K. Pretreatment of the samples with soluble fibrin prior to SDS-PAGE enhanced the amount but not the position of the FA-UK activity on the zymogram, indicating that the complex was not dissociated by fibrin. Pretreatment with hydroxylamine (1M) eradicated the FA-UK activity in urine. Addition of UK or pro-UK to urine followed by concentration (X10), increased the 100K band on the zymogram. Under conditions of this experiment, it was shown that little conversion of pro-UK to UK occurred suggesting that complexation occurs with pro-UK as well as with UK. Moreover, a - 100K FA-UK band on zymography was demonstrated afer addition of pro-UK to urine treated with DFP (5mM) or GGAck (20juM) to inactivate UK.It was concluded that a - 50K inhibitor in urine, with properties similar to an inhibitor described by Stump et al (JBC 261:12759, 86), acts as a co-factor for fibrin binding of UK and possibly also of pro-UK. It is speculated that this co-factor may contribute to the fibrin-specificity of pro-UK by localizing both it and its activated derivative, UK, to the fibrin surface.
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