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Collect. Czech. Chem. Commun. 2000, 65, 243-266
https://doi.org/10.1135/cccc20000243

Crystal Structures and Reactivity of 3a,5a,8a,10a-Tetraazaperhydropyrene Derivatives. An Alternative Approach to Selective Nitrogen Alkylation of 1,4,8,11-Tetraazacyclotetradecane (Cyclam)

Jan Kotek, Petr Hermann*, Pavel Vojtíšek, Jan Rohovec and Ivan Lukeš

Department of Inorganic Chemistry, Charles University, Hlavova 2030, 128 40 Prague 2, Czech Republic

Crossref Cited-by Linking

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  • Kanaoujiya Rahul, Singh Dharmveer, Minocha Tarun, Yadav Sanjeev Kumar, Srivastava Shekhar: Synthesis, characterization of ruthenium (III) macrocyclic complexes of 1,4,8,11-tetraazacyclotetradecane(cyclam) and in vitro assessment of anti-cancer activity. Materials Today: Proceedings 2022, 65, 3143. <https://doi.org/10.1016/j.matpr.2022.05.354>
  • AlHaddad Nancy, Lelong Evan, Suh Jong-Min, Cordier Marie, Lim Mi Hee, Royal Guy, Platas-Iglesias Carlos, Bernard Hélène, Tripier Raphaël: Copper(ii) and zinc(ii) complexation with N-ethylene hydroxycyclams and consequences on the macrocyclic backbone configuration. Dalton Trans. 2022, 51, 8640. <https://doi.org/10.1039/D2DT00941B>
  • Paúrová Monika, David Tomáš, Císařová Ivana, Lubal Přemysl, Hermann Petr, Kotek Jan: Optimization of the selectivity and rate of copper radioisotope complexation: formation and dissociation kinetic studies of 1,4,8-trimethylcyclam-based ligands with different coordinating pendant arms. New J. Chem. 2018, 42, 11908. <https://doi.org/10.1039/C8NJ00419F>
  • Bartoli Francesco, Bencini Andrea, Conti Luca, Giorgi Claudia, Valtancoli Barbara, Paoli Paola, Rossi Patrizia, Le Bris Nathalie, Tripier Raphael: Catching anions with coloured assemblies: binding of pH indicators by a giant-size polyammonium macrocycle for anion naked-eye recognition. Org. Biomol. Chem. 2016, 14, 8309. <https://doi.org/10.1039/C6OB01474G>
  • Paúrová Monika, Havlíčková Jana, Pospíšilová Aneta, Vetrík Miroslav, Císařová Ivana, Stephan Holger, Pietzsch Hans‐Jürgen, Hrubý Martin, Hermann Petr, Kotek Jan: Bifunctional Cyclam‐Based Ligands with Phosphorus Acid Pendant Moieties for Radiocopper Separation: Thermodynamic and Kinetic Studies. Chemistry A European J 2015, 21, 4671. <https://doi.org/10.1002/chem.201405777>
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  • Camus Nathalie, Halime Zakaria, Le Bris Nathalie, Bernard Hélène, Platas-Iglesias Carlos, Tripier Raphaël: Full Control of the Regiospecific N-Functionalization of C-Functionalized Cyclam Bisaminal Derivatives and Application to the Synthesis of their TETA, TE2A, and CB-TE2A Analogues. J. Org. Chem. 2014, 79, 1885. <https://doi.org/10.1021/jo4028566>
  • Silversides Jon D., Burke Benjamin P., Archibald Stephen J.: Rapid synthesis of cross-bridged cyclam chelators for copper(II) complex formation. Comptes Rendus. Chimie 2013, 16, 524. <https://doi.org/10.1016/j.crci.2013.02.013>
  • Bernier Nicolas, Esteves Catarina V., Delgado Rita: Heteroditopic receptor based on crown ether and cyclen units for the recognition of zwitterionic amino acids. Tetrahedron 2012, 68, 4860. <https://doi.org/10.1016/j.tet.2012.03.110>
  • Bernier Nicolas, Costa Judite, Delgado Rita, Félix Vítor, Royal Guy, Tripier Raphaël: trans-Methylpyridine cyclen versus cross-bridged trans-methylpyridine cyclen. Synthesis, acid–base and metal complexation studies (metal = Co2+, Cu2+, and Zn2+). Dalton Trans 2011, 40, 4514. <https://doi.org/10.1039/c0dt01191f>
  • Silversides Jon D., Smith Rachel, Archibald Stephen J.: Challenges in chelating positron emitting copper isotopes: tailored synthesis of unsymmetric chelators to form ultra stable complexes. Dalton Trans 2011, 40, 6289. <https://doi.org/10.1039/c0dt01395a>
  • Miéville Pascal, Jaccard Hugues, Reviriego Felipe, Tripier Raphaël, Helm Lothar: Synthesis, complexation and NMR relaxation properties of Gd3+ complexes of Mes(DO3A)3. Dalton Trans 2011, 40, 4260. <https://doi.org/10.1039/c0dt01597k>
  • Delépine Anne‐Sophie, Tripier Raphaël, Le Baccon Michel, Handel Henri: From Flexible to Constrained Tris(tetraamine) Ligands: Synthesis, Acid–Base Properties, and Structural Effect on the Coordination Process with Nucleotides. Eur J Org Chem 2010, 2010, 5380. <https://doi.org/10.1002/ejoc.201000495>
  • Bencini Andrea, Biagini Silvia, Giorgi Claudia, Handel Henri, Le Baccon Michel, Mariani Palma, Paoletti Piero, Paoli Paola, Rossi Patrizia, Tripier Raphaël, Valtancoli Barbara: A Tris‐Macrocycle with Proton Sponge Characteristics as Efficient Receptor for Inorganic Phosphate and Nucleotide Anions. Eur J Org Chem 2009, 2009, 5610. <https://doi.org/10.1002/ejoc.200900770>
  • Delépine Anne-Sophie, Tripier Raphaël, Bernard Hélène, Bris Nathalie Le, Handel Henri: Selective mono-N-alkylation of triethylenetetraamine. A new versatile route to polylinear aza-ligands. Tetrahetron Lett 2009, 50, 2521. <https://doi.org/10.1016/j.tetlet.2009.03.088>
  • Plutnar Jan, Havlíčková Jana, Kotek Jan, Hermann Petr, Lukeš Ivan: Unsymmetrically substituted side-bridged cyclam derivatives and their Cu(ii) and Zn(ii) complexes. New J. Chem. 2008, 32, 496. <https://doi.org/10.1039/B709747F>
  • Doménech Antonio, García-España Enrique, Bernier Nicolas, Tripier Raphaël, Handel Henri: Electrochemically-driven conformational shift in mono- and di-copper constrained macrotricyclic cyclen receptors. Dalton Trans. 2008, 3169. <https://doi.org/10.1039/b718163a>
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  • Vitha Tomáš, Kotek Jan, Rudovský Jakub, Kubíček Vojtěch, Císařová Ivana, Hermann Petr, Lukeš Ivan: Selective Protection of 1,4,8,11-Tetraazacyclotetradecane (Cyclam) in Position 1,4 with the Phosphonothioyl Group and Synthesis of a Cyclam-1,4-bis(methylphosphonic Acid). Crystal Structures of Several Cyclic Phosphonothioamides. Collect. Czech. Chem. Commun. 2006, 71, 337. <https://doi.org/10.1135/cccc20060337>
  • Claudon Géraldine, Bernard Hélène, Le Bris Nathalie, Handel Henri: Synthesis of three dissymmetrical pentaamines via bisaminals of linear tetraamines. Journal of Chemical Research 2006, 2006, 356. <https://doi.org/10.3184/030823406777946860>
  • Claudon Géraldine, Le Bris Nathalie, Bernard Hélène, Handel Henri: Powerful N‐Monoalkylation of Linear Tetraamines via Bisaminal Intermediates. Eur J Org Chem 2004, 2004, 5027. <https://doi.org/10.1002/ejoc.200400459>
  • Fensterbank Hélène, Berthault Patrick, Larpent Chantal: A Tunable One‐Step N,N′‐Disubstitution of 1,4,8,11‐Tetraazacyclotetradecane with Acrylamide. Eur J Org Chem 2003, 2003, 3985. <https://doi.org/10.1002/ejoc.200300133>
  • Develay Stéphanie, Tripier Raphaël, Chuburu Françoise, Le Baccon Michel, Handel Henri: A New Versatile Synthesis of Macrotricyclic Tetraazacycloalkane‐Based Ligands from Bis‐aminal Derivatives. Eur J Org Chem 2003, 2003, 3047. <https://doi.org/10.1002/ejoc.200300188>
  • Bernard Hélène, Del Rio Garcia Eugenia, Ferec Sonia, Kervarec Nelly, Handel Henri: The Unexpected Conversion of 1,5,8,12‐Tetraazadodecane‐Glyoxal Bisaminal into Its Amidinium Salt in an Acidic Medium. Eur J Org Chem 2003, 2003, 255. <https://doi.org/10.1002/ejoc.200390026>
  • Tripier Raphaël, Chuburu Françoise, Le Baccon Michel, Handel Henri: Phenylglyoxal for polyamines modification and cyclam synthesis. Tetrahedron 2003, 59, 4573. <https://doi.org/10.1016/S0040-4020(03)00656-2>
  • Kotek Jan, Hermann Petr, Vojtisek Pavel, Rohovec Jan, Lukes Ivan: ChemInform Abstract: Crystal Structures and Reactivity of 3a,5a,8a,10a‐Tetraazaperhydropyrene Derivatives. An Alternative Approach to Selective Nitrogen Alkylation of 1,4,8‐11‐Tetraazacyclotetradecane (Cyclam). ChemInform 2000, 31. <https://doi.org/10.1002/chin.200029126>
  • Wong Edward H., Weisman Gary R., Hill Daniel C., Reed David P., Rogers Mark E., Condon Jeffrey S., Fagan Maureen A., Calabrese Joseph C., Lam Kin-Chung, Guzei Ilia A., Rheingold Arnold L.: Synthesis and Characterization of Cross-Bridged Cyclams and Pendant-Armed Derivatives and Structural Studies of Their Copper(II) Complexes. J. Am. Chem. Soc. 2000, 122, 10561. <https://doi.org/10.1021/ja001295j>
  • Kotek Jan, Vojtíšek Pavel, Císařová Ivana, Hermann Petr, Jurečka Petr, Rohovec Jan, Lukeš Ivan: Bis(methylphosphonic Acid) Derivatives of 1,4,8,11-Tetraazacyclotetradecane (Cyclam). Synthesis, Crystal and Molecular Structures, and Solution Properties. Collect. Czech. Chem. Commun. 2000, 65, 1289. <https://doi.org/10.1135/cccc20001289>