697
Views
102
CrossRef citations to date
0
Altmetric
Research Article

REDUCTION OF N-HYDROXYLATED COMPOUNDS: AMIDOXIMES (N-HYDROXYAMIDINES) AS PRO-DRUGS OF AMIDINES

Pages 565-579 | Published online: 25 Jul 2002

Keep up to date with the latest research on this topic with citation updates for this article.

Read on this site (7)

M. Prabhuswamy, Dinesha, K. J. Pampa, S. Madan Kumar, G. K. Nagaraja & N. K. Lokanath. (2014) Synthesis, Crystal Structure and Characterization of (Z)-2-N′-hydroxyisonicotinamidine. Molecular Crystals and Liquid Crystals 593:1, pages 243-252.
Read now
Danilo Froriep, Bernd Clement, Florian Bittner, Ralf R. Mendel, Debora Reichmann, Wolfgang Schmalix & Antje Havemeyer. (2013) Activation of the anti-cancer agent upamostat by the mARC enzyme system. Xenobiotica 43:9, pages 780-784.
Read now
Antje Havemeyer, Juliane Lang & Bernd Clement. (2011) The fourth mammalian molybdenum enzyme mARC: current state of research. Drug Metabolism Reviews 43:4, pages 524-539.
Read now
Joscha Kotthaus, Torsten Steinmetzer, Andreas van de Locht & Bernd Clement. (2011) Analysis of highly potent amidine containing inhibitors of serine proteases and their N-hydroxylated prodrugs (amidoximes). Journal of Enzyme Inhibition and Medicinal Chemistry 26:1, pages 115-122.
Read now
R. Reh, J. Ozols & B. Clement. (2008) Involvement of stearoyl-CoA desaturase in the reduction of amidoxime prodrugs. Xenobiotica 38:9, pages 1177-1190.
Read now
J. H Ansede, R. D Voyksner, M. A Ismail, D. W Boykin, R. R Tidwell & J. E Hall. (2005) In vitro metabolism of an orally active O-methyl amidoxime prodrug for the treatment of CNS trypanosomiasis. Xenobiotica 35:3, pages 211-226.
Read now
A. K. Fröhlich, U. Girreser & B Clement. (2005) Metabolism of benzamidoxime (N-hydroxyamidine) in human hepatocytes and role of UDP-glucuronosyltransferases. Xenobiotica 35:1, pages 17-25.
Read now

Articles from other publishers (95)

Michel A. Struwe, Axel J. Scheidig & Bernd Clement. (2023) The mitochondrial amidoxime reducing component—from prodrug-activation mechanism to drug-metabolizing enzyme and onward to drug target. Journal of Biological Chemistry 299:11, pages 105306.
Crossref
Bernd Clement & Michel A. Struwe. (2023) The History of mARC. Molecules 28:12, pages 4713.
Crossref
Somayeh Behrouz, Nikos Kühl & Christian D. Klein. (2023) N-sulfonyl peptide-hybrids as a new class of dengue virus protease inhibitors. European Journal of Medicinal Chemistry 251, pages 115227.
Crossref
Crystall Swarbrick, Vasiliki Zogali, Kitti Wing Ki Chan, Dimitrios Kiousis, Chin Piaw Gwee, Sai Wang, Julien Lescar, Dahai Luo, Mark von Itzstein, Minos-Timotheos Matsoukas, George Panagiotakopoulos, Subhash G. Vasudevan & Gerasimos Rassias. (2021) Amidoxime prodrugs convert to potent cell-active multimodal inhibitors of the dengue virus protease. European Journal of Medicinal Chemistry 224, pages 113695.
Crossref
Li-Juan Yu, Duncan A. Cullen, Mahbod Morshedi, Michelle L. Coote & Nicholas G. White. (2021) Room Temperature Hydrolysis of Benzamidines and Benzamidiniums in Weakly Basic Water. The Journal of Organic Chemistry 86:19, pages 13762-13767.
Crossref
Somayeh Behrouz, Nikos Kühl & Christian D. Klein. (2021) A facile approach towards amidinophenylalanine derivatives as building blocks for the synthesis of non-natural peptides and peptidomimetics. Tetrahedron Letters 81, pages 153342.
Crossref
Nejib Jebli, Youssef Arfaoui, Kristof Van Hecke, Jean-François Cavalier & Soufiane Touil. (2021) Experimental and computational investigation of Z/E isomerism, X-ray crystal structure and molecular docking study of (2-(hydroxyimino)cyclohexyl)diphenylphosphine sulfide, a potential antibacterial agent. Journal of Molecular Structure 1229, pages 129634.
Crossref
Islam M. A. Mekhemer, Abdel-Aal M. Gaber & Morsy M. M. Aly. (2020) Production of Amidinyl Radicals via UV–Vis-Light Promoted Reduction of N -Arylthiophene-2-carboxamidoximes and Application to the Preparation of Some New N -Arylthiophene-2-carboxamidines . ACS Omega 5:44, pages 28712-28721.
Crossref
Nejib Jebli, Selma Hamimed, Kristof Van Hecke, Jean‐François Cavalier & Soufiane Touil. (2020) Synthesis, Antimicrobial Activity and Molecular Docking Study of Novel α ‐(Diphenylphosphoryl)‐ and α ‐(Diphenylphosphorothioyl)cycloalkanone Oximes . Chemistry & Biodiversity 17:8.
Crossref
Volodymyr A. Tkachuk, Olga V. Hordiyenko, Irina V. Omelchenko, Volodomir V. Medviediev & Axelle Arrault. (2018) Methyl esters of 2-(N-hydroxycarbamimidoyl)benzoyl-substituted α-amino acids as promising building blocks in peptidomimetic synthesis: a comparative study. Monatshefte für Chemie - Chemical Monthly 149:12, pages 2293-2309.
Crossref
Takeshi Fuchigami, Noriko Fujimoto, Terushi Haradahira, Yumiko Nojiri, Takashi Okauchi, Jun Maeda, Tetsuya Suhara, Fumihiko Yamamoto, Morio Nakayama, Minoru Maeda & Takahiro Mukai. (2018) Synthesis and characterization of 11 C-labeled benzyl amidine derivatives as PET radioligands for GluN2B subunit of the NMDA receptors . Journal of Labelled Compounds and Radiopharmaceuticals 61:14, pages 1095-1105.
Crossref
Dipak S. Dalal, Dipak R. Patil & Yogesh A. Tayade. (2018) β‐Cyclodextrin: A Green and Efficient Supramolecular Catalyst for Organic Transformations. The Chemical Record 18:11, pages 1560-1582.
Crossref
James W. Janetka & Robert A. GalemmoJrJr. 2018. Extracellular Targeting of Cell Signaling in Cancer. Extracellular Targeting of Cell Signaling in Cancer 247 275 .
D. S. Bolotin. (2018) Reactions of Amidoximes with Metal-Activated Nitriles. Russian Journal of Coordination Chemistry 44:4, pages 243-251.
Crossref
Alexander S. Novikov & Dmitrii S. Bolotin. (2018) Tautomerism of amidoximes and other oxime species. Journal of Physical Organic Chemistry 31:3, pages e3772.
Crossref
B. F. Parker, S. Hohloch, J. R. Pankhurst, Z. Zhang, J. B. Love, J. Arnold & L. Rao. (2018) Interactions of vanadium( iv ) with amidoxime ligands: redox reactivity . Dalton Transactions 47:16, pages 5695-5702.
Crossref
Tianwei Weng, Xiaqiu Qiu, Jubo Wang, Zhiyu Li & Jinlei Bian. (2018) Recent discovery of indoleamine-2,3-dioxygenase 1 inhibitors targeting cancer immunotherapy. European Journal of Medicinal Chemistry 143, pages 656-669.
Crossref
Torsten Steinmetzer & Kornelia Hardes. 2018. Activation of Viruses by Host Proteases. Activation of Viruses by Host Proteases 279 325 .
Teodora Ivanova, Kornelia Hardes, Stephanie Kallis, Sven O. Dahms, Manuel E. Than, Sebastian Künzel, Eva Böttcher-Friebertshäuser, Iris Lindberg, Guan-Sheng Jiao, Ralf Bartenschlager & Torsten Steinmetzer. (2017) Optimization of Substrate-Analogue Furin Inhibitors. ChemMedChem 12:23, pages 1953-1968.
Crossref
Zahra Nasresfahani, Mohammad Zaman Kassaee & Esmaiel Eidi. (2017) Ionic liquid‐functionalized mesoporous silica nanoparticles ([pmim]FeCl 4 /MSNs): Efficient nanocatalyst for solvent‐free synthesis of N , N ′‐diaryl‐substituted formamidines . Applied Organometallic Chemistry 31:11.
Crossref
Dmitrii S. Bolotin, Zarina M. Bikbaeva, Alexander S. Novikov, Vitalii V. Suslonov & Nadezhda A. Bokach. (2017) A Dimetallic Aminonitrone Nickel(II) Complex: Further Insights into Metal-Mediated Nucleophilic Activation of Amidoximes. ChemistrySelect 2:30, pages 9674-9678.
Crossref
Olga Ovdiichuk, Olga Hordiyenko, Evgenia Fotou, Caroline Gaucher, Axelle Arrault & Marie-Christine Averlant-Petit. (2016) Conformational studies of new pseudotripeptide with pyrazine amidoxime motif and simplified analogs using IR, NMR spectroscopy, and molecular dynamic simulations. Structural Chemistry 28:3, pages 813-822.
Crossref
Saurav Paul, Ashalata Roy, Suman Jyoti Deka, Subhankar Panda, Vishal Trivedi & Debasis Manna. (2016) Nitrobenzofurazan derivatives of N′-hydroxyamidines as potent inhibitors of indoleamine-2,3-dioxygenase 1. European Journal of Medicinal Chemistry 121, pages 364-375.
Crossref
J. Boer, R. Young-Sciame, F. Lee, K. J. Bowman, X. Yang, J. G. Shi, F. M. Nedza, W. Frietze, L. Galya, A. P. Combs, S. Yeleswaram & S. Diamond. (2016) Roles of UGT, P450, and Gut Microbiota in the Metabolism of Epacadostat in Humans. Drug Metabolism and Disposition 44:10, pages 1668-1674.
Crossref
Dmitrii S. Bolotin, Nadezhda A. Bokach & Vadim Yu. Kukushkin. (2016) Coordination chemistry and metal-involving reactions of amidoximes: Relevance to the chemistry of oximes and oxime ligands. Coordination Chemistry Reviews 313, pages 62-93.
Crossref
Shuvam Pramanik, Sima Roy, Tapas Ghorui, Sanjib Ganguly & Kausikisankar Pramanik. (2016) Iridium(III) Mediated Reductive Transformation of Closed-Shell Azo-Oxime to Open-Shell Azo-Imine Radical Anion: Molecular and Electronic Structure, Electron Transfer, and Optoelectronic Properties. Inorganic Chemistry 55:4, pages 1461-1468.
Crossref
Lena F. Weigel, Christoph Nitsche, Dominik Graf, Ralf Bartenschlager & Christian D. Klein. (2015) Phenylalanine and Phenylglycine Analogues as Arginine Mimetics in Dengue Protease Inhibitors. Journal of Medicinal Chemistry 58:19, pages 7719-7733.
Crossref
Yesim Saniye Kara. (2015) 13C NMR substituent-induced chemical shifts in 4-(substituted phenyl)-3-phenyl-1,2,4-oxadiazol-5(4H)-ones (thiones). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 149, pages 920-927.
Crossref
Dmitrii S. Bolotin, Marina Ya. Demakova, Alexander S. Novikov, Margarita S. Avdontceva, Maxim L. Kuznetsov, Nadezhda A. Bokach & Vadim Yu. Kukushkin. (2015) Bifunctional Reactivity of Amidoximes Observed upon Nucleophilic Addition to Metal-Activated Nitriles. Inorganic Chemistry 54:8, pages 4039-4046.
Crossref
Gudrun Ott, Antje Havemeyer & Bernd Clement. (2014) The mammalian molybdenum enzymes of mARC. JBIC Journal of Biological Inorganic Chemistry 20:2, pages 265-275.
Crossref
Gerhard Gross. 2015. The Practice of Medicinal Chemistry. The Practice of Medicinal Chemistry 631 655 .
Björn Cohrs, Yi Zhao, Ulf Lützen, Juraj Culman, Bernd Clement & Maaz Zuhayra. (2014) In vivo SPECT imaging of [123I]-labeled pentamidine pro-drugs for the treatment of human African trypanosomiasis, pharmacokinetics, and bioavailability studies in rats. International Journal of Pharmaceutics 477:1-2, pages 167-175.
Crossref
Gudrun Ott, Birte Plitzko, Carmen Krischkowski, Debora Reichmann, Florian Bittner, Ralf R. Mendel, Thomas Kunze, Bernd Clement & Antje Havemeyer. (2014) Reduction of Sulfamethoxazole Hydroxylamine (SMX-HA) by the Mitochondrial Amidoxime Reducing Component (mARC). Chemical Research in Toxicology 27:10, pages 1687-1695.
Crossref
Nikolay S. Ilyinsky, Anna K. Shchyolkina, Olga F. Borisova, Olga K. Mamaeva, Maria I. Zvereva, Dulat M. Azhibek, Mikhail A. Livshits, Vladimir A. Mitkevich, Jan Balzarini, Yuri B. Sinkevich, Yuri N. Luzikov, Lybov G. Dezhenkova, Ekaterina S. Kolotova, Alexander A. Shtil, Andrey E. Shchekotikhin & Dmitry N. Kaluzhny. (2014) Novel multi-targeting anthra[2,3-b]thiophene-5,10-diones with guanidine-containing side chains: Interaction with telomeric G-quadruplex, inhibition of telomerase and topoisomerase I and cytotoxic properties. European Journal of Medicinal Chemistry 85, pages 605-614.
Crossref
Adrian-Raul Tomsa, Yanling Li, Sébastien Blanchard, Patrick Herson, Kamal Boubekeur, Pierre Gouzerh & Anna Proust. (2013) Oxo-Centered Trinuclear Chromium(III) Complexes with Both Carboxylate and Amidoximate Ligands. Journal of Cluster Science 25:3, pages 825-838.
Crossref
Gudrun Ott, Debora Reichmann, Cornelia Boerger, Ingolf Cascorbi, Florian Bittner, Ralf-Rainer Mendel, Thomas Kunze, Bernd Clement & Antje Havemeyer. (2014) Functional Characterization of Protein Variants Encoded by Nonsynonymous Single Nucleotide Polymorphisms in MARC1 and MARC2 in Healthy Caucasians . Drug Metabolism and Disposition 42:4, pages 718-725.
Crossref
Laura Schwarz, Ulrich Girreser & Bernd Clement. (2014) Synthesis and Characterization of para -Substituted N , N′- Dihydroxybenzamidines and Their Derivatives as Model Compounds for a Class of Prodrugs . European Journal of Organic Chemistry 2014:9, pages 1961-1975.
Crossref
Mélissa Degardin, Sharon Wein, Jean-Frédéric Duckert, Marjorie Maynadier, Alexandre Guy, Thierry Durand, Roger Escale, Henri Vial & Yen Vo-Hoang. (2014) Development of the First Oral Bioprecursors of Bis-alkylguanidine Antimalarial Drugs. ChemMedChem 9:2, pages 300-304.
Crossref
F. Peter Guengerich & Emre M. Isin. 2014. Handbook of Metabolic Pathways of Xenobiotics. Handbook of Metabolic Pathways of Xenobiotics 1 51 .
Bashir Ahmad Dar, Syed Naseer Ahmad, Mohammad Arif Wagay, Altaf Hussain, Nisar Ahmad, Khursheed Ahmad Bhat, Mohammad Akbar Khuroo, Meena Sharma & Baldev Singh. (2013) Ultrasound promoted expeditious, catalyst-free and solvent-free approach for the synthesis of N,N′-diarylsubstituted formamidines at room temperature. Tetrahedron Letters 54:36, pages 4880-4884.
Crossref
Stefan Dosa, Marit Stirnberg, Verena Lülsdorff, Daniela Häußler, Eva Maurer & Michael Gütschow. (2012) Active site mapping of trypsin, thrombin and matriptase-2 by sulfamoyl benzamidines. Bioorganic & Medicinal Chemistry 20:21, pages 6489-6505.
Crossref
Dipak R. Patil & Dipak S. Dalal. (2012) Biomimetic approach for the synthesis of N,N′-diarylsubstituted formamidines catalyzed by β-cyclodextrin in water. Chinese Chemical Letters 23:10, pages 1125-1128.
Crossref
Mélissa Degardin, Sharon Wein, Smitha Gouni, Christophe Tran Van Ba, Jean-Frédéric Duckert, Thierry Durand, Roger Escale, Henri Vial & Yen Vo-Hoang. (2012) Evaluation of Bis-Alkylamidoxime O -Alkylsulfonates as Orally Available Antimalarials . ChemMedChem 7:6, pages 991-1001.
Crossref
Akinori Okano, Robert C. James, Joshua G. Pierce, Jian Xie & Dale L. Boger. (2012) Silver(I)-Promoted Conversion of Thioamides to Amidines: Divergent Synthesis of a Key Series of Vancomycin Aglycon Residue 4 Amidines That Clarify Binding Behavior to Model Ligands. Journal of the American Chemical Society 134:21, pages 8790-8793.
Crossref
Alan R. Katritzky, Longchuan Huang, Mamta Chahar, Rajeev Sakhuja & C. Dennis Hall. (2012) The Chemistry of N -Hydroxyamidoximes, N -Aminoamidoximes, and Hydrazidines . Chemical Reviews 112:3, pages 1633-1649.
Crossref
Joscha Kotthaus, Jürke Kotthaus, Dennis Schade, Ulrike Schwering, Helen Hungeling, Helge Müller-Fielitz, Walter Raasch & Bernd Clement. (2011) New Prodrugs of the Antiprotozoal Drug Pentamidine. ChemMedChem 6:12, pages 2233-2242.
Crossref
George T. Lountos, Andrew G. Jobson, Joseph E. Tropea, Christopher R. Self, Guangtao Zhang, Yves Pommier, Robert H. Shoemaker & David S. Waugh. (2011) Structural characterization of inhibitor complexes with checkpoint kinase 2 (Chk2), a drug target for cancer therapy. Journal of Structural Biology 176:3, pages 292-301.
Crossref
Joscha Kotthaus, Helen Hungeling, Christiane Reeh, Jürke Kotthaus, Dennis Schade, Silvia Wein, Siegfried Wolffram & Bernd Clement. (2011) Synthesis and biological evaluation of l-valine-amidoximeesters as double prodrugs of amidines. Bioorganic & Medicinal Chemistry 19:6, pages 1907-1914.
Crossref
Li Ren, Steve Wenglowsky, Greg Miknis, Bryson Rast, Alex J. Buckmelter, Robert J. Ely, Stephen Schlachter, Ellen R. Laird, Nikole Randolph, Michele Callejo, Matthew Martinson, Sarah Galbraith, Barbara J. Brandhuber, Guy Vigers, Tony Morales, Walter C. Voegtli & Joseph Lyssikatos. (2011) Non-oxime inhibitors of B-RafV600E kinase. Bioorganic & Medicinal Chemistry Letters 21:4, pages 1243-1247.
Crossref
Lidia Nieto, Ainhoa Mascaraque, Florence Miller, Fabienne Glacial, Carlos Ríos Martínez, Marcel Kaiser, Reto Brun & Christophe Dardonville. (2010) Synthesis and Antiprotozoal Activity of N -Alkoxy Analogues of the Trypanocidal Lead Compound 4,4′-Bis(imidazolinylamino)diphenylamine with Improved Human Blood−Brain Barrier Permeability . Journal of Medicinal Chemistry 54:2, pages 485-494.
Crossref
Victor R. Guarino. 2010. Prodrugs and Targeted Delivery. Prodrugs and Targeted Delivery 31 60 .
Alexander Schröder, Jürke Kotthaus, Dennis Schade, Bernd Clement & Klaus Rehse. (2010) Arylazoamidoximes and Related Compounds as NO‐modulators. Archiv der Pharmazie 343:1, pages 9-16.
Crossref
Dennis Schade, Joscha Kotthaus, Helen Hungeling, Jürke Kotthaus & Bernd Clement. (2009) The Peptidylglycine α-Amidating Monooxygenase (PAM): A Novel Prodrug Strategy for Amidoximes and N -Hydroxyguanidines? . ChemMedChem 4:10, pages 1595-1599.
Crossref
Mélissa Degardin, Sharon Wein, Thierry Durand, Roger Escale, Henry Vial & Yen Vo-Hoang. (2009) N-substituted bis-C-alkyloxadiazolones as dual effectors: Efficient intermediates to amidoximes or amidines and prodrug candidates of potent antimalarials. Bioorganic & Medicinal Chemistry Letters 19:17, pages 5233-5236.
Crossref
Svetlana M. Bakunova, Stanislav A. Bakunov, Tanja Wenzler, Todd Barszcz, Karl A. Werbovetz, Reto Brun & Richard R. Tidwell. (2009) Synthesis and Antiprotozoal Activity of Pyridyl Analogues of Pentamidine. Journal of Medicinal Chemistry 52:15, pages 4657-4667.
Crossref
Svetlana M. Bakunova, Stanislav A. Bakunov, Donald A. Patrick, E. V. K. Suresh Kumar, Kwasi A. Ohemeng, Arlene S. Bridges, Tanja Wenzler, Todd Barszcz, Susan Kilgore Jones, Karl A. Werbovetz, Reto Brun & Richard R. Tidwell. (2009) Structure−Activity Study of Pentamidine Analogues as Antiprotozoal Agents. Journal of Medicinal Chemistry 52:7, pages 2016-2035.
Crossref
Peter Hlavica. (2009) Assembly of non-natural electron transfer conduits in the cytochrome P450 system: A critical assessment and update of artificial redox constructs amenable to exploitation in biotechnological areas. Biotechnology Advances 27:2, pages 103-121.
Crossref
Mahama Ouattara, Sharon Wein, Séverine Denoyelle, Stéphanie Ortial, Thierry Durand, Roger Escale, Henri Vial & Yen Vo-Hoang. (2009) Design and synthesis of amidoxime derivatives for orally potent C-alkylamidine-based antimalarial agents. Bioorganic & Medicinal Chemistry Letters 19:3, pages 624-626.
Crossref
Sanja Gruenewald, Bettina Wahl, Florian Bittner, Helen Hungeling, Stephanie Kanzow, Joscha Kotthaus, Ulrike Schwering, Ralf R. Mendel & Bernd Clement. (2008) The Fourth Molybdenum Containing Enzyme mARC: Cloning and Involvement in the Activation of N -Hydroxylated Prodrugs . Journal of Medicinal Chemistry 51:24, pages 8173-8177.
Crossref
Ainhoa Mascaraque, Lidia Nieto & Christophe Dardonville. (2008) Efficient one-pot synthesis of 1-alkoxy-2-arylaminoimidazolines from N-alkoxy-N-(2-aminoethyl)-2-nitrobenzenesulfonamides and arylisothiocyanates. Tetrahedron Letters 49:31, pages 4571-4574.
Crossref
W. David Wilson, Farial A. Tanious, Amanda Mathis, Denise Tevis, James Edwin Hall & David W. Boykin. (2008) Antiparasitic compounds that target DNA. Biochimie 90:7, pages 999-1014.
Crossref
Jarkko Rautio, Hanna Kumpulainen, Tycho Heimbach, Reza Oliyai, Dooman Oh, Tomi Järvinen & Jouko Savolainen. (2008) Prodrugs: design and clinical applications. Nature Reviews Drug Discovery 7:3, pages 255-270.
Crossref
Anu J. Airaksinen, Jan Andersson, Phong Truong, Olle Karlsson & Christer Halldin. (2008) Radiosynthesis of [ 11 C]ximelagatran via palladium catalyzed [ 11 C]cyanation . Journal of Labelled Compounds and Radiopharmaceuticals 51:1, pages 1-5.
Crossref
M P Barrett, D W Boykin, R Brun & R R Tidwell. (2007) Human African trypanosomiasis: pharmacological re-engagement with a neglected disease. British Journal of Pharmacology 152:8, pages 1155-1171.
Crossref
Christiane Reeh, Judith Wundt & Bernd Clement. (2007) N , N ′-Dihydroxyamidines: A New Prodrug Principle To Improve the Oral Bioavailability of Amidines . Journal of Medicinal Chemistry 50:26, pages 6730-6734.
Crossref
Roberta Del Sole, Agnese De Luca, Massimo Catalano, Giuseppe Mele & Giuseppe Vasapollo. (2007) Noncovalent imprinted microspheres: Preparation, evaluation and selectivity of DBU template. Journal of Applied Polymer Science 105:4, pages 2190-2197.
Crossref
John I. Trujillo, Horng-Chih Huang, William L. Neumann, Matthew W. Mahoney, Scott Long, Wei Huang, Danny J. Garland, Carrie Kusturin, Zaheer Abbas, Michael S. South & David B. Reitz. (2007) Design, synthesis, and biological evaluation of pyrazinones containing novel P1 needles as inhibitors of TF/VIIa. Bioorganic & Medicinal Chemistry Letters 17:16, pages 4568-4574.
Crossref
Anne Stürzebecher, Daniel Dönnecke, Andrea Schweinitz, Oliver Schuster, Peter Steinmetzer, Uta Stürzebecher, Joscha Kotthaus, Bernd Clement, Jörg Stürzebecher & Torsten Steinmetzer. (2007) Highly Potent and Selective Substrate Analogue Factor Xa Inhibitors ContainingD-Homophenylalanine Analogues as P3 Residue: Part 2. ChemMedChem 2:7, pages 1043-1053.
Crossref
Bernard Testa & Stefanie D. Krämer. (2007) The Biochemistry of Drug Metabolism – An Introduction. Chemistry & Biodiversity 4:3, pages 257-405.
Crossref
Mahama Ouattara, Sharon Wein, Michèle Calas, Yen Vo Hoang, Henri Vial & Roger Escale. (2007) Synthesis and antimalarial activity of new 1,12-bis(N,N′-acetamidinyl)dodecane derivatives. Bioorganic & Medicinal Chemistry Letters 17:3, pages 593-596.
Crossref
B. Testa. 2007. Comprehensive Medicinal Chemistry II. Comprehensive Medicinal Chemistry II 1009 1041 .
W.F. Trager. 2007. Comprehensive Medicinal Chemistry II. Comprehensive Medicinal Chemistry II 87 132 .
Olafur S. Gudmundsson. 2007. Prodrugs. Prodrugs 1395 1402 .
Jefferson W. Tilley. 2007. Prodrugs. Prodrugs 889 922 .
Bernd Clement, Anja Bürenheide, Wolfgang Rieckert & Jörg Schwarz. (2006) Diacetyldiamidoximeester of Pentamidine, a Prodrug for Treatment of Protozoal Diseases: Synthesis, in vitro and in vivo Biotransformation. ChemMedChem 1:11, pages 1260-1267.
Crossref
Antje Havemeyer, Florian Bittner, Silke Wollers, Ralf Mendel, Thomas Kunze & Bernd Clement. (2006) Identification of the Missing Component in the Mitochondrial Benzamidoxime Prodrug-converting System as a Novel Molybdenum Enzyme. Journal of Biological Chemistry 281:46, pages 34796-34802.
Crossref
Alan R. Katritzky, Niveen M. Khashab, Nataliya Kirichenko & Anamika Singh. (2006) Microwave-Assisted Preparations of Amidrazones and Amidoximes. The Journal of Organic Chemistry 71:24, pages 9051-9056.
Crossref
Bernd Clement, Thomas Kunze & Sabine Heberling. (2006) Reduction of Nω-hydroxy-l-arginine to l-arginine by pig liver microsomes, mitochondria, and human liver microsomes. Biochemical and Biophysical Research Communications 349:2, pages 869-873.
Crossref
Christophe Dardonville, Michael P. Barrett, Reto Brun, Marcel Kaiser, Farial Tanious & W. David Wilson. (2006) DNA Binding Affinity of Bisguanidine and Bis(2-aminoimidazoline) Derivatives with in Vivo Antitrypanosomal Activity. Journal of Medicinal Chemistry 49:12, pages 3748-3752.
Crossref
Larisa Oresmaa, Paula Aulaskari & Pirjo Vainiotalo. (2006) Electrospray ionization mass spectrometric studies of some imidazole amidoximes and nitrolic acids and their esters. Rapid Communications in Mass Spectrometry 20:7, pages 1071-1076.
Crossref
Jennifer R. Riggs, Aleksandr Kolesnikov, John Hendrix, Wendy B. Young, William D. Shrader, Dange Vijaykumar, Robin Stephens, Liang Liu, Lin Pan, Joyce Mordenti, Michael J. Green & Juthamas Sukbuntherng. (2006) Factor VIIa inhibitors: A prodrug strategy to improve oral bioavailability. Bioorganic & Medicinal Chemistry Letters 16:8, pages 2224-2228.
Crossref
John R. CashmanJun Zhang. (2006) HUMAN FLAVIN-CONTAINING MONOOXYGENASES. Annual Review of Pharmacology and Toxicology 46:1, pages 65-100.
Crossref
Sabine Heberling, Ulrich Girreser, Stephanie Wolf & Bernd Clement. (2006) Oxygen-insensitive enzymatic reduction of oximes to imines. Biochemical Pharmacology 71:3, pages 354-365.
Crossref
Bernd Clement, Sabine Mau, Stephanie Deters & Antje Havemeyer. (2005) HEPATIC, EXTRAHEPATIC, MICROSOMAL, AND MITOCHONDRIAL ACTIVATION OF THE N -HYDROXYLATED PRODRUGS BENZAMIDOXIME, GUANOXABENZ, AND RO 48-3656 ([[1-[(2 S )-2-[[4-[(HYDROXYAMINO)IMINOMETHYL]BENZOYL]AMINO]-1-OXOPROPYL]-4-PIPERIDINYL]OXY]-ACETIC ACID) . Drug Metabolism and Disposition 33:11, pages 1740-1747.
Crossref
Reem K. Arafa, Reto Brun, Tanja Wenzler, Farial A. Tanious, W. David Wilson, Chad E. Stephens & David W. Boykin. (2005) Synthesis, DNA Affinity, and Antiprotozoal Activity of Fused Ring Dicationic Compounds and Their Prodrugs. Journal of Medicinal Chemistry 48:17, pages 5480-5488.
Crossref
Bernd Clement, Detlef Behrens, Juliane Amschler, Katrin Matschke, Stephanie Wolf & Antje Havemeyer. (2005) Reduction of sulfamethoxazole and dapsone hydroxylamines by a microsomal enzyme system purified from pig liver and pig and human liver microsomes. Life Sciences 77:2, pages 205-219.
Crossref
Susanne Andersson, Yvonne Hofmann, Åsa Nordling, Xue-qing Li, Sabina Nivelius, Tommy B. Andersson, Magnus Ingelman-Sundberg & Inger Johansson. (2005) CHARACTERIZATION AND PARTIAL PURIFICATION OF THE RAT AND HUMAN ENZYME SYSTEMS ACTIVE IN THE REDUCTION OF N -HYDROXYMELAGATRAN AND BENZAMIDOXIME . Drug Metabolism and Disposition 33:4, pages 570-578.
Crossref
Joseph R. Kurian, Sunil U. Bajad, Jackie L. Miller, Nathaniel A. Chin & Lauren A. Trepanier. (2004) NADH Cytochrome b 5 Reductase and Cytochrome b 5 Catalyze the Microsomal Reduction of Xenobiotic Hydroxylamines and Amidoximes in Humans . Journal of Pharmacology and Experimental Therapeutics 311:3, pages 1171-1178.
Crossref
Thomas Kurz & Khalid Widyan. (2004) Efficient Conversion of O-Substituted 3-Hydroxy-4-imino-oxazolidin-2-ones into O-Substituted α-Hydroxyamidoximes. Organic Letters 6:24, pages 4403-4405.
Crossref
Kenneth W.J. Baker, Katherine S. Horner, Stephen A. Moggach, R. Michael Paton & Iain A.S. Smellie. (2004) Synthesis of pyranosyl amidoximes by addition of amines to pyranosyl nitrile oxides. Tetrahedron Letters 45:48, pages 8913-8916.
Crossref
John H. Ansede, Mariappan Anbazhagan, Reto Brun, Judy D. Easterbrook, James Edwin Hall & David W. Boykin. (2004) O -Alkoxyamidine Prodrugs of Furamidine:  In Vitro Transport and Microsomal Metabolism as Indicators of in Vivo Efficacy in a Mouse Model of Trypanosoma brucei rhodesiense Infection . Journal of Medicinal Chemistry 47:17, pages 4335-4338.
Crossref
John R Cashman. (2004) The implications of polymorphisms in mammalian flavin-containing monooxygenases in drug discovery and development. Drug Discovery Today 9:13, pages 574-581.
Crossref
Peter Ettmayer, Gordon L. Amidon, Bernd Clement & Bernard Testa. (2004) Lessons Learned from Marketed and Investigational Prodrugs. Journal of Medicinal Chemistry 47:10, pages 2393-2404.
Crossref
Anamarija Zega, Gregor Mlinšek, Tomaž Šolmajer, Alenka Trampuš-Bakija, Mojca Stegnar & Uroš Urleb. (2004) Thrombin inhibitors built on an azaphenylalanine scaffold. Bioorganic & Medicinal Chemistry Letters 14:6, pages 1563-1567.
Crossref
Bernd Clement & Katrin Lopian. (2003) Characterization of in Vitro Biotransformation of New, Orally Active, Direct Thrombin Inhibitor Ximelagatran, an Amidoxime and Ester Prodrug. Drug Metabolism and Disposition 31:5, pages 645-651.
Crossref

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.