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Journal articles on the topic 'Benzamidoxime'

Author: Grafiati

Published: 4 June 2021

Last updated: 7 February 2022

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1

Clement, Bernd, Sigrid Schmitt, and Martin Zimmermann. "Enzymatic Reduction of Benzamidoxime to Benzamidoxine." Archiv der Pharmazie 321, no. 12 (1988): 955–56. http://dx.doi.org/10.1002/ardp.19883211228.

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2

Grambal, František, and Jan Lasovský. "Cyclization of O-benzoylbenzamidoxime derivatives in water-alcohol media." Collection of Czechoslovak Chemical Communications 50, no. 12 (1985): 2722–29. http://dx.doi.org/10.1135/cccc19852722.

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O-Benzoylated benzamidoximes give 1,2,4-oxadiazoles (yields above 90%) in water-alcoholic media of pH = 2.45 to 6.20. The cyclization rate has been studied with 28 derivatives containing different substituents. The reaction is accelerated by electron-donor substituents at 4-position of benzamidoxime and by electron-acceptor substituents at 4'-position of benzoyl. The dependence of the rate constants vs σ values of the substituents fulfils the two-parameter Hammett equation at a 99% probability level. The activation parameters have been determined, and effects of polarity of medium, kinetic iso

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3

Grambal, František, and Jan Lasovský. "Cyclization and acid-catalyzed hydrolysis of O-benzoylbenzamidoximes." Collection of Czechoslovak Chemical Communications 51, no. 12 (1986): 2786–97. http://dx.doi.org/10.1135/cccc19862786.

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Kinetics of formation of 1,2,4-oxadiazoles from 24 substitution derivatives of O-benzoylbenzamidoxime have been studied in sulphuric acid and aqueous ethanol media. It has been found that this medium requires introduction of the Hammett H0 function instead of the pH scale beginning as low as from 0.1% solutions of mineral acids. Effects of the acid concentration, ionic strength, and temperature on the reaction rate and on the kinetic isotope effect have been followed. From these dependences and from polar effects of substituents it was concluded that along with the cyclization to 1,2,4-oxadiaz

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4

Abellán-López, Antonio, María-Teresa Chicote, Delia Bautista, and José Vicente. "Cyclopalladated complexes derived from benzamidoxime." Dalton Trans. 43, no. 2 (2014): 592–98. http://dx.doi.org/10.1039/c3dt51867a.

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5

Carpenter, G. B., and R. M. Srivastava. "Structure of a chloral–benzamidoxime adduct." Acta Crystallographica Section C Crystal Structure Communications 43, no. 4 (1987): 695–97. http://dx.doi.org/10.1107/s0108270187094472.

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6

Yarovenko, V. N., I. V. Zavarzin, and M. M. Krayushkin. "Reaction of organic nitriles with benzamidoxime." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 35, no. 5 (1986): 1106. http://dx.doi.org/10.1007/bf00955403.

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7

Clement, B., and M. Zimmermann. "Characteristics of the microsomalN-hydroxylation of benzamidine to benzamidoxime." Xenobiotica 17, no. 6 (1987): 659–67. http://dx.doi.org/10.3109/00498258709043973.

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8

Möhrle, Hans, and Jürgen Lessel. "Quecksilber(II)-EDTA-DehydrierungN- undO-funktionalisierter 2-tert-Amino-benzamidoxime." Archiv der Pharmazie 324, no. 5 (1991): 313–15. http://dx.doi.org/10.1002/ardp.19913240511.

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9

Kara, Yesim S., Seda G. Sagdinc, and Nevzat Karadayı. "Experimental and theoretical investigations of 4-chloro-N-(2-methoxyphenyl)benzamidoxime." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 110 (June 2013): 351–63. http://dx.doi.org/10.1016/j.saa.2013.03.035.

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10

PARK, Yoon-Yul, Seong-Yun KIM, Jung-Sung KIM, et al. "Complex Formation of U(VI) with Benzamidoxime in Non-aqueous Solvents." Journal of Nuclear Science and Technology 37, no. 4 (2000): 344–48. http://dx.doi.org/10.1080/18811248.2000.9714904.

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11

Fröhlich, A. K., U. Girreser, and B. Clement. "Metabolism of benzamidoxime (N-hydroxyamidine) in human hepatocytes and role of UDP-glucuronosyltransferases." Xenobiotica 35, no. 1 (2005): 17–25. http://dx.doi.org/10.1080/00498250400021895.

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12

Horvat, Melissa, Tanja‐Saskia Larch, Florian Rudroff, and Margit Winkler. "Amino Benzamidoxime (ABAO)‐Based Assay to Identify Efficient Aldehyde‐Producing Pichia pastoris Clones." Advanced Synthesis & Catalysis 362, no. 21 (2020): 4673–79. http://dx.doi.org/10.1002/adsc.202000558.

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13

Il'in, V. V., E. V. Kabakchi, and A. V. Ignatenko. "Reactions of benzamidoxime and its sodium salt with methyl esters of fluorinated acids." Russian Chemical Bulletin 42, no. 3 (1993): 485–87. http://dx.doi.org/10.1007/bf00698437.

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14

Wang, Hui, Huiqin Yao, Lihong Chen, et al. "Highly efficient capture of uranium from seawater by layered double hydroxide composite with benzamidoxime." Science of The Total Environment 759 (March 2021): 143483. http://dx.doi.org/10.1016/j.scitotenv.2020.143483.

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15

Clement, B., P. Schmezer, H. Weber, J. R. Schlehofer, S. Schmitt, and B. L. Pool. "Genotoxic activities of benzamidine and itsN-hydroxylated metabolite benzamidoxime inSalmonella typhimurium and mammalian cells." Journal of Cancer Research and Clinical Oncology 114, no. 4 (1988): 363–68. http://dx.doi.org/10.1007/bf02128179.

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16

Clement, Bernd, Detlef Behrens, Wenke Möller, and John R. Cashman. "Reduction of Amphetamine Hydroxylamine and Other Aliphatic Hydroxylamines by Benzamidoxime Reductase and Human Liver Microsomes." Chemical Research in Toxicology 13, no. 10 (2000): 1037–45. http://dx.doi.org/10.1021/tx000043t.

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17

Thipyapong, Khajadpai, Tomoya Uehara, Keisuke Suzuki, Yasushi Arano, and Vithaya Ruangpornvisuti. "IR spectroscopic and DFT investigations on molecular conformations of thio-free oxo technetium (V) benzamidoxime complexes." Journal of Molecular Structure 990, no. 1-3 (2011): 152–57. http://dx.doi.org/10.1016/j.molstruc.2011.01.034.

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18

Clement, Bernd, Rüdiger Lomb, and Wenke Möller. "Isolation and Characterization of the Protein Components of the Liver Microsomal O2-insensitive NADH-Benzamidoxime Reductase." Journal of Biological Chemistry 272, no. 31 (1997): 19615–20. http://dx.doi.org/10.1074/jbc.272.31.19615.

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19

Havemeyer, Antje, Florian Bittner, Silke Wollers, Ralf Mendel, Thomas Kunze, and Bernd Clement. "Identification of the Missing Component in the Mitochondrial Benzamidoxime Prodrug-converting System as a Novel Molybdenum Enzyme." Journal of Biological Chemistry 281, no. 46 (2006): 34796–802. http://dx.doi.org/10.1074/jbc.m607697200.

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20

Kim, S. Y., M. Harada, H. Tomiyasu, Y. Ikeda, and Y. Y. Park. "Structure and kinetic studies of U(VI)-benzamidoxime complex in non-aqueous solutions by 1H- and 13C-NMR." Progress in Nuclear Energy 37, no. 1-4 (2000): 399–404. http://dx.doi.org/10.1016/s0149-1970(00)00078-0.

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21

Thipyapong, Khajadpai, Tomoya Uehara, Yuji Tooyama, Henrik Braband, Roger Alberto, and Yasushi Arano. "Insight into Technetium Amidoxime Complex: Oxo Technetium(V) Complex ofN-Substituted Benzamidoxime as New Basic Structure for Molecular Imaging." Inorganic Chemistry 50, no. 3 (2011): 992–98. http://dx.doi.org/10.1021/ic101714q.

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22

Srivastava, Rajendra M., Manuel Braga, Ricardo Longo, and Nereide S. S. Magalhães. "Ab initio and semiempirical (AM1) structural studies of O-(2,2,2-trichloro-1-hydroxyethyl)-benzamidoxime and its hydrogen bonded dimer." Journal of Molecular Structure 375, no. 3 (1996): 267–72. http://dx.doi.org/10.1016/0022-2860(95)09058-4.

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23

Srivastava, Rajendra M., Manuel Braga, Ricardo Longo, and Nereide S. S. Magalhães. "Ab initio and semiempirical (AM1) structural studies of O-(2,2,2-trichloro-1-hydroxyethyl)-benzamidoxime and its hydrogen bonded dimer." Journal of Molecular Structure: THEOCHEM 375, no. 3 (1996): 267–72. http://dx.doi.org/10.1016/0166-1280(96)91085-4.

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24

Andersson, Susanne, Yvonne Hofmann, Åsa Nordling, et al. "CHARACTERIZATION AND PARTIAL PURIFICATION OF THE RAT AND HUMAN ENZYME SYSTEMS ACTIVE IN THE REDUCTION OF N-HYDROXYMELAGATRAN AND BENZAMIDOXIME." Drug Metabolism and Disposition 33, no. 4 (2005): 570–78. http://dx.doi.org/10.1124/dmd.104.002972.

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25

IL'IN, V. V., E. V. KABAKCHI, and A. V. IGNATENKO. "ChemInform Abstract: Reactions of Benzamidoxime (I) and Its Sodium Salt (V) with Methyl Esters (II), (VII), (IX) of Fluorinated Acids." ChemInform 25, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.199420167.

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26

Fritzer-Szekeres, Monika, Ladislav Novotny, Anna Vachalkova, Rainer Göbl, Howard L. Elford, and Thomas Szekeres. "Iron binding capacity of didox (3,4-dihydroxy benzohydroxamic acid) and amidox (3,4-dihydroxy benzamidoxime) two inhibitors of the enzyme ribonucleotide reductase." Clinical Biochemistry 30, no. 3 (1997): 255. http://dx.doi.org/10.1016/s0009-9120(97)87684-9.

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27

Clement, Bernd, Sabine Mau, Stephanie Deters, and Antje Havemeyer. "HEPATIC, EXTRAHEPATIC, MICROSOMAL, AND MITOCHONDRIAL ACTIVATION OF THE N-HYDROXYLATED PRODRUGS BENZAMIDOXIME, GUANOXABENZ, AND RO 48-3656 ([[1-[(2S)-2-[[4-[(HYDROXYAMINO)IMINOMETHYL]BENZOYL]AMINO]-1-OXOPROPYL]-4-PIPERIDINYL]OXY]-ACETIC ACID)." Drug Metabolism and Disposition 33, no. 11 (2005): 1740–47. http://dx.doi.org/10.1124/dmd.105.005249.

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28

Exner, Otto, and Nedelko Motekov. "Dipole moments and conformation of some aromatic benzamidoximes." Collection of Czechoslovak Chemical Communications 51, no. 7 (1986): 1444–49. http://dx.doi.org/10.1135/cccc19861444.

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Dipole moments of aromatic benzamidoximes I - VI were measured in benzene solution. Assuming the Z configuration as established previously on another set of similar derivatives, some details of conformation could be determined, e.g. the position of an unsymmetrically substituted aromatic ring or mutual position of several methoxy groups.

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29

de Morais, Lécia P. F., Fernando Hallwass, I. Malvestiti, and Rajendra M. Srivastava. "Benzamidoximes. II. A 15N NMR study." Journal of Molecular Structure 782, no. 2-3 (2006): 200–203. http://dx.doi.org/10.1016/j.molstruc.2005.07.020.

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30

Srivastava, Rajendra M., Ira M. Brinn, Juan O. Machuca-Herrera, et al. "Benzamidoximes: structural, conformational and spectroscopic studies. I." Journal of Molecular Structure 406, no. 1-2 (1997): 159–67. http://dx.doi.org/10.1016/s0022-2860(96)09452-5.

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31

Clement, Bernd, Martina Immel, Sigrid Schmitt, and Udo Steinmann. "Biotransformations of Benzamidine and Benzamidoximein vivo." Archiv der Pharmazie 326, no. 10 (1993): 807–12. http://dx.doi.org/10.1002/ardp.19933261008.

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32

Möhrle, Hans, та Jürgen Lessel. "Ν,Ν-Disubstituierte Amidoxim-Nachbargruppen in Cyclodehydrierungen / Assistance of Ν,Ν-Disubstituted Amidoximes in Cyclodehydrogenation Reactions". Zeitschrift für Naturforschung B 47, № 9 (1992): 1333–40. http://dx.doi.org/10.1515/znb-1992-0920.

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o-(tert-Amino)benzamidoximes 6, Ν,Ν-disubstituted at the amid-N-atom of the nucleophilic moiety, are suitable neighbouring groups in cyclodehydrogenation reactions of tertiary amines using mercury(II)-edta. The kind of the N-substituents and the amount of oxidizing agent control the nature of the products, lactams 9 and anellated nitrones 8. The configuration of the tricyclic systems is determined by NMR spectroscopic methods. During the reaction an inversion of the configuration of the oxime moiety occurs, which is explained by an electrocyclic mechanism.

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33

Girreser, U., M. König, and B. Clement. "Characterization ofpara-substituted benzamidoximes and benzamidinium salts by15N NMR spectroscopy." Magnetic Resonance in Chemistry 40, no. 3 (2002): 202–6. http://dx.doi.org/10.1002/mrc.999.

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34

Vassileva, Penka, and Galin Petrov. "Kupfer(II)-Komplexe von p-Nitrophenylacetamidoxim und p-Acetylamino-benzamidoxim." Zeitschrift für Chemie 22, no. 3 (2010): 111–12. http://dx.doi.org/10.1002/zfch.19820220313.

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35

Clement, Bernd, Martin Zimmermann, and Sigrid Schmitt. "Biotransformation des Benzamidins und des Benzamidoxims durch mikrosomale Enzyme vom Kaninchen." Archiv der Pharmazie 322, no. 7 (1989): 431–35. http://dx.doi.org/10.1002/ardp.19893220710.

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36

Medeiros, Herbert Igor Rodrigues de, Bruna Barbosa Maia da Silva, Carlos Eduardo Rodrigues Aguiar, et al. "SÍNTESE E AVALIAÇÃO TOXICOLÓGICA DA BENZAMIDOXIMA FRENTE A LARVAS DE ARTEMIA SALINA LEACH." Brazilian Journal of Development 6, no. 8 (2020): 57940–45. http://dx.doi.org/10.34117/bjdv6n8-269.

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37

Risitano, Francesco, Giovanni Grassi, Franceso Foti, and Fabrizio Filocamo. "5-exo-trigonal cyclization and [3,5] rearrangement of N-aryl benzamidoximes by reaction with nitrile oxides." Tetrahedron 53, no. 3 (1997): 1089–98. http://dx.doi.org/10.1016/s0040-4020(96)01032-0.

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38

RISITANO, F., G. GRASSI, F. FOTI, and F. FILOCAMO. "ChemInform Abstract: 5-exo-Trigonal Cyclization and (3,5) Rearrangement of N-Aryl Benzamidoximes by Reaction with Nitrile Oxides." ChemInform 28, no. 16 (2010): no. http://dx.doi.org/10.1002/chin.199716067.

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39

Bauch, Eva, Debora Reichmann, Ralf-Rainer Mendel, et al. "Electrochemical and mARC-Catalyzed Enzymatic Reduction ofpara-Substituted Benzamidoximes: Consequences for the Prodrug Concept “Amidoximes instead of Amidines”." ChemMedChem 10, no. 2 (2014): 360–67. http://dx.doi.org/10.1002/cmdc.201402437.

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40

Burianova, V. K., and D. S. Bolotin. "Electronic effect of substituents in coupling reactions between para-substituted benzamidoximes and nitrile ligands in cis-[PtCl2(EtCN)2] complex." Russian Journal of General Chemistry 85, no. 12 (2015): 2721–24. http://dx.doi.org/10.1134/s1070363215120099.

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41

Morais, Maria Franncielly Simões de, Herbert Igor Rodrigues de Medeiros, Maria Thaynara Jorge, Érick Caique Santos Costa, Juliano Carlo Rufino Freitas, and Egberto dos Santos Carmo. "Síntese do 2-(3-fenil-1,2,4-oxadiazol-5-il)fenol e avaliação do seu potencial toxicológico e antifúngico." Research, Society and Development 9, no. 7 (2020): e601974523. http://dx.doi.org/10.33448/rsd-v9i7.4523.

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Nos últimos anos, as micoses têm se tornado um grave problema de saúde pública, principalmente, devido ao aumento do número de pessoas com imunodeficiência, inata ou adquirida, e pelo surgimento de microrganismos multiresistentes decorrente do uso indiscriminado de antibióticos. A fim de minimizar esses problemas, compostos contendo o anel 1,2,4-oxadiazólico são alvo de inúmeros estudos farmacológicos e toxicológicos visando desenvolver novos antimicrobianos mais potentes e seletivos. Deste modo, o presente estudo objetivou avaliar o potencial toxicológico e antifúngico do composto 2-(3-fenil-

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42

HARADA, Kazuho, Jun-ichi YOKOYAMA, Hiroaki TAKAYANAGI, Haruo OGURA, and Shonosuke ZEN. "The Synthetic Reactions of Aliphatic Nitro Compounds. XXVI. Synthesis of (Z)-N-(5-(3-Aryl)-(1,2,4)oxadiazolyl)-N-((methylcarbamoyl)methyl)benzamidoximes." CHEMICAL & PHARMACEUTICAL BULLETIN 40, no. 6 (1992): 1610–11. http://dx.doi.org/10.1248/cpb.40.1610.

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43

CLEMENT, B., S. SCHMITT, and M. ZIMMERMANN. "ChemInform Abstract: Enzymatic Reduction of Benzamidoxime to Benzamidine." ChemInform 20, no. 24 (1989). http://dx.doi.org/10.1002/chin.198924315.

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44

YAROVENKO, V. N., I. V. ZAVARZIN, and M. M. KRAYUSHKIN. "ChemInform Abstract: Reaction of Organic Nitriles with Benzamidoxime." ChemInform 18, no. 1 (1987). http://dx.doi.org/10.1002/chin.198701190.

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45

Araujo Almeida, Claudia Lais, Jonh Anderson Macedo Santos, Cosme Silva Santos, et al. "Benzamidoxime-Mediated Crotylation of Aldehydes using Potassium (Z) and (E)-Crotyltrifluoroborates." Journal of the Mexican Chemical Society 62, no. 1 (2018). http://dx.doi.org/10.29356/jmcs.v62i1.577.

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A highly diastereoselective protocol for the crotylation reaction of aldehydes using potassium (<em>Z</em>) and (<em>E</em>)-crotytrifluoroborates was developed. Benzamidoxime was employed as a renewable catalyst, which was easily recovered through a simple extraction process. This method proved to be simple, fast, regio- and chemoselective for different aldehydes. The corresponding homoallylic alcohols were obtained in good to excellent yields without the need of further purification.

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46

Schwendenwein, Daniel, Anna K. Ressmann, Mark Doerr, et al. "Random Mutagenesis‐Driven Improvement of Carboxylate Reductase Activity using an Amino Benzamidoxime‐Mediated High‐Throughput Assay." Advanced Synthesis & Catalysis, April 11, 2019. http://dx.doi.org/10.1002/adsc.201900155.

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47

Amitai, Gabriel, Alexander Plotnikov, Shira Chapman, et al. "Non-quaternary oximes detoxify nerve agents and reactivate nerve agent-inhibited human butyrylcholinesterase." Communications Biology 4, no. 1 (2021). http://dx.doi.org/10.1038/s42003-021-02061-w.

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AbstractGovernment-sanctioned use of nerve agents (NA) has escalated dramatically in recent years. Oxime reactivators of organophosphate (OP)-inhibited acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) serve as antidotes toward poisoning by OPNAs. The oximes used as therapeutics are quaternary compounds that cannot penetrate the blood–brain barrier (BBB). There remains an urgent need for the development of next generation OPNA therapeutics. We have developed two high-throughput screening (HTS) assays using a fluorogenic NA surrogate, O-ethyl methylphosphonyl O-4-methyl-3-cyano-couma

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