{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,24]],"date-time":"2026-08-24T15:02:12Z","timestamp":1787583732157,"version":"build-2736575974"},"reference-count":79,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2025,4,4]],"date-time":"2025-04-04T00:00:00Z","timestamp":1743724800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Latvia\u2013Lithuania\u2013Taiwan","award":["LV-LT-TW\/2022\/9"],"award-info":[{"award-number":["LV-LT-TW\/2022\/9"]}]},{"name":"Latvia\u2013Lithuania\u2013Taiwan","award":["50602NB"],"award-info":[{"award-number":["50602NB"]}]},{"name":"Latvia\u2013Lithuania\u2013Taiwan","award":["LV-FR\/2024\/5"],"award-info":[{"award-number":["LV-FR\/2024\/5"]}]},{"name":"Latvian Council of Science","award":["LV-LT-TW\/2022\/9"],"award-info":[{"award-number":["LV-LT-TW\/2022\/9"]}]},{"name":"Latvian Council of Science","award":["50602NB"],"award-info":[{"award-number":["50602NB"]}]},{"name":"Latvian Council of Science","award":["LV-FR\/2024\/5"],"award-info":[{"award-number":["LV-FR\/2024\/5"]}]},{"name":"PHC Osmosis program project","award":["LV-LT-TW\/2022\/9"],"award-info":[{"award-number":["LV-LT-TW\/2022\/9"]}]},{"name":"PHC Osmosis program project","award":["50602NB"],"award-info":[{"award-number":["50602NB"]}]},{"name":"PHC Osmosis program project","award":["LV-FR\/2024\/5"],"award-info":[{"award-number":["LV-FR\/2024\/5"]}]},{"name":"Purine-based carbenes: synthesis, photophysical and optical studies (PBC)","award":["LV-LT-TW\/2022\/9"],"award-info":[{"award-number":["LV-LT-TW\/2022\/9"]}]},{"name":"Purine-based carbenes: synthesis, photophysical and optical studies (PBC)","award":["50602NB"],"award-info":[{"award-number":["50602NB"]}]},{"name":"Purine-based carbenes: synthesis, photophysical and optical studies (PBC)","award":["LV-FR\/2024\/5"],"award-info":[{"award-number":["LV-FR\/2024\/5"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Purine-1,4,7,10-tetraazacyclododecane (cyclen) conjugate was designed to study its Cu2+ ions complexation capability. Several synthetic approaches were tested to achieve the target compound. The optimal approach involved stepwise modifications of purine N9, C8, and C6 positions that, in nine consecutive steps, provided purine\u2013cyclen conjugate. The synthetic sequence involved Mitsunobu-type alkylation at N9 and iodination at C8, followed by Stille, SNAr, CuAAC, and alkylation reactions. The designed purine\u2013cyclen conjugate is able to complex Cu2+ ions in both the cyclen part and between the purine N7 and triazole N2 positions. The complexation pattern and equilibrium were studied using the NMR titration technique in MeCN-d3 and absorption spectra.<\/jats:p>","DOI":"10.3390\/molecules30071612","type":"journal-article","created":{"date-parts":[[2025,4,4]],"date-time":"2025-04-04T06:52:56Z","timestamp":1743749576000},"page":"1612","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Synthesis of Purine-1,4,7,10-Tetraazacyclododecane Conjugate and Its Complexation Modes with Copper(II)"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0009-0007-9042-6644","authenticated-orcid":false,"given":"Aleksejs","family":"Burcevs","sequence":"first","affiliation":[{"name":"Institute of Chemistry and Chemical Technology, Faculty of Natural Sciences and Technology, Riga Technical University, P. 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Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1123","DOI":"10.1016\/j.jacc.2009.04.089","article-title":"Regadenoson: A New Myocardial Stress Agent","volume":"54","author":"Iskandrian","year":"2009","journal-title":"J. Am. Coll. Cardiol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"14379","DOI":"10.1021\/acs.chemrev.6b00209","article-title":"Metabolism, Biochemical Actions, and Chemical Synthesis of Anticancer Nucleosides, Nucleotides, and Base Analogs","volume":"116","author":"Shelton","year":"2016","journal-title":"Chem. Rev."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2880","DOI":"10.1021\/cr900028p","article-title":"Enzymology of Purine and Pyrimidine Antimetabolites Used in the Treatment of Cancer","volume":"109","author":"Parker","year":"2009","journal-title":"Chem. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1043","DOI":"10.1038\/nchem.2859","article-title":"Fluorescent Nucleobases as Tools for Studying DNA and RNA","volume":"9","author":"Xu","year":"2017","journal-title":"Nat. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2579","DOI":"10.1021\/cr900301e","article-title":"Fluorescent Analogs of Biomolecular Building Blocks: Design, Properties, and Applications","volume":"110","author":"Sinkeldam","year":"2010","journal-title":"Chem. Rev."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"245","DOI":"10.1002\/chem.201102349","article-title":"Site-Specific Control of N7-Metal Coordination in DNA by a Fluorescent Purine Derivative","volume":"18","author":"Dumas","year":"2012","journal-title":"Chem.-A Eur. J."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"6158","DOI":"10.1021\/jp303138s","article-title":"Application of a Fluorescent C-Linked Phenolic Purine Adduct for Selective N7-Metalation of DNA","volume":"116","author":"Omumi","year":"2012","journal-title":"J. Phys. Chem. B"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1894","DOI":"10.1021\/ja068416l","article-title":"Biomarkers for Phenol Carcinogen Exposure Act as pH-Sensing Fluorescent Probes","volume":"129","author":"Sun","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2185","DOI":"10.1021\/am405345h","article-title":"Purine-Stabilized Green Fluorescent Gold Nanoclusters for Cell Nuclei Imaging Applications","volume":"6","author":"Venkatesh","year":"2014","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"5554","DOI":"10.1021\/acs.analchem.6b01395","article-title":"Nucleoside-Based Ultrasensitive Fluorescent Probe for the Dual-Mode Imaging of Microviscosity in Living Cells","volume":"88","author":"Li","year":"2016","journal-title":"Anal. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"108437","DOI":"10.1016\/j.dyepig.2020.108437","article-title":"Purine-Based Thermally Activated Delayed Fluorescence Emitters for Efficient Organic Light-Emitting Diodes","volume":"180","author":"Wang","year":"2020","journal-title":"Dye. Pigment."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"334","DOI":"10.1016\/j.jinorgbio.2015.11.029","article-title":"Neomycin B-Cyclen Conjugates and Their Zn(II) Complexes as RNA-Binding Agents","volume":"162","author":"Kong","year":"2016","journal-title":"J. Inorg. Biochem."},{"key":"ref_14","unstructured":"Wexler, P. (2014). Hydrogen Sulfide. Encyclopedia of Toxicology, Elsevier. [3rd ed.]."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"6916","DOI":"10.1021\/ic300784v","article-title":"Monopicolinate Cyclen and Cyclam Derivatives for Stable Copper(II) Complexation","volume":"51","author":"Lima","year":"2012","journal-title":"Inorg. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Delgado, R., F\u00e9lix, V., Lima, L.M.P., and Price, D.W. (2007). Metal Complexes of Cyclen and Cyclam Derivatives Useful for Medical Applications: A Discussion Based on Thermodynamic Stability Constants and Structural Data. Dalt. Trans., 2734\u20132745.","DOI":"10.1039\/B704360K"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"14300","DOI":"10.1039\/D4DT01791A","article-title":"A Combined Solid State, Solution and DFT Study of a Dimethyl-Cyclen-Pd(II) Complex","volume":"53","author":"Paderni","year":"2024","journal-title":"Dalt. Trans."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"119","DOI":"10.1039\/D1CE01096D","article-title":"Structurally Characterised New Twisted Conformer for Cyclen, Controlled by Metal Ion Complexation as Seen in NiII and CuII complexes with Halides and Pseudohalides","volume":"24","author":"Verma","year":"2022","journal-title":"CrystEngComm"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"7137","DOI":"10.1002\/anie.201203014","article-title":"Copper Catalyst Activation Driven by Photoinduced Electron Transfer: A Prototype Photolatent Click Catalyst","volume":"51","author":"Harmand","year":"2012","journal-title":"Angew. Chemie-Int. Ed."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"4753","DOI":"10.1021\/acs.joc.9b03518","article-title":"Sulfonyl Group Dance: A Tool for the Synthesis of 6-Azido-2-Sulfonylpurine Derivatives","volume":"85","author":"Ozols","year":"2020","journal-title":"J. Org. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"193","DOI":"10.1081\/NCN-120019521","article-title":"Convenient Synthesis of 8-Amino-2\u2032-Deoxyadenosine","volume":"22","author":"Frieden","year":"2003","journal-title":"Nucleosides Nucleotides Nucleic Acids"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"410","DOI":"10.3762\/bjoc.17.37","article-title":"1,2,3-Triazoles as Leaving Groups: SNAr Reactions of 2,6-Bistriazolylpurines with O- And C-Nucleophiles","volume":"17","author":"Novosjolova","year":"2021","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2131","DOI":"10.1039\/c0gc00517g","article-title":"Microwave Irradiated C6-Functionalization of 6-Chloropurine Nucleosides with Various Mild Nucleophiles under Solvent-Free Conditions","volume":"12","author":"Guo","year":"2010","journal-title":"Green Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"5974","DOI":"10.1021\/jm9006356","article-title":"Structure-Activity Relationships of Adenine and Deazaadenine Derivatives as Ligands for Adenine Receptors, a New Purinergic Receptor Family","volume":"52","author":"Borrmann","year":"2009","journal-title":"J. Med. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"9912","DOI":"10.1021\/acs.jmedchem.0c01017","article-title":"Medicinal Chemistry Optimization of a Diaminopurine Chemotype: Toward a Lead for Trypanosoma Brucei Inhibitors","volume":"63","author":"Singh","year":"2020","journal-title":"J. Med. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"6523","DOI":"10.1016\/j.bmc.2017.10.032","article-title":"Trisubstituted Purine Inhibitors of PDGFR\u03b1 and Their Antileukemic Activity in the Human Eosinophilic Cell Line EOL-1","volume":"25","author":"Jorda","year":"2017","journal-title":"Bioorg. Med. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3629","DOI":"10.1002\/ejoc.201403527","article-title":"Synthesis and Applications of Azolylpurine and Azolylpurine Nucleoside Derivatives","volume":"2015","author":"Novosjolova","year":"2015","journal-title":"Eur. J. Org. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1091","DOI":"10.1016\/j.bmc.2003.12.008","article-title":"Synthesis and Evaluation of 2-Substituted 8-Hydroxyadenines as Potent Interferon Inducers with Improved Oral Bioavailabilities","volume":"12","author":"Kurimoto","year":"2004","journal-title":"Bioorg. Med. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"3759","DOI":"10.1021\/acs.orglett.7b01602","article-title":"Modular, Step-Efficient Palladium-Catalyzed Cross-Coupling Strategy to Access C6-Heteroaryl 2-Aminopurine Ribonucleosides","volume":"19","author":"Buchanan","year":"2017","journal-title":"Org. Lett."},{"key":"ref_30","first-page":"1704","article-title":"The Suzuki-Miyaura Cross-Coupling Reactions of 2-, 6- or 8-Halopurines with Boronic Acids Leading to 2-, 6- or 8-Aryl- and -Alkenylpurine Derivatives","volume":"11","author":"Hocek","year":"2001","journal-title":"Synthesis"},{"key":"ref_31","first-page":"187","article-title":"Applications of Boronic Acids in Selective C-C and C-N Arylation of Purines","volume":"52","author":"Strouse","year":"2005","journal-title":"Acta Chim. Slov."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"7663","DOI":"10.1039\/c1ob06265d","article-title":"Nickel-Catalyzed Negishi Cross-Couplings of 6-Chloropurines with Organozinc Halides at Room Temperature","volume":"9","author":"Wang","year":"2011","journal-title":"Org. Biomol. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"7237","DOI":"10.1016\/S0040-4020(97)00427-4","article-title":"Preparation and Reactions of New Zincated Nitrogen-Containing Heterocycles","volume":"53","author":"Prasad","year":"1997","journal-title":"Tetrahedron"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"366","DOI":"10.3891\/acta.chem.scand.53-0366","article-title":"Regiochemistry in the Pd-Mediated Coupling between 6,8-Dihalopurines and Organometallic Reagents","volume":"53","author":"Gundersen","year":"1999","journal-title":"Acta Chem. Scand."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1945","DOI":"10.1016\/0040-4039(95)00163-7","article-title":"Regioselective Pd-Mediated Coupling between 2,6-Dichloropurines and Organometallic Reagents","volume":"36","author":"Gundersen","year":"1995","journal-title":"Tetrahedron Lett."},{"key":"ref_36","unstructured":"Kapdi, A.R., Maiti, D., and Sanghvi, Y.S. (2018). Sonogashira Cross-Coupling: Alkyne-Modified Nucleosides and Their Applications. Palladium-Catalyzed Modification of Nucleosides, Nucleotides and Oligonucleotides, Elsevier."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"305","DOI":"10.1016\/j.tetlet.2010.11.033","article-title":"Regioselective Sonogashira Cross-Coupling Reactions of 6-Chloro-2,8-diiodo-9-THP-9H-purine with Alkyne Derivatives","volume":"52","author":"Ibrahim","year":"2011","journal-title":"Tetrahedron Lett."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"7160","DOI":"10.1002\/ejoc.201501026","article-title":"Synthesis of 5-\/8-Halogenated or Ethynylated Lipophilic Nucleobases as Potential Synthetic Intermediates for Supramolecular Chemistry","volume":"2015","author":"Bilbao","year":"2015","journal-title":"Eur. J. Org. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2869","DOI":"10.1055\/s-2004-834881","article-title":"Regioselectivity in Cross-Coupling Reactions of 2,6,8-Trichloro-9-(Tetrahydropyran-2-Yl)Purine: Synthesis of 2,6,8-Trisubstituted Purine Bases","volume":"36","author":"Hocek","year":"2004","journal-title":"Synthesis"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"889","DOI":"10.1055\/s-2004-816012","article-title":"Dichotomy in Regioselective Cross-Coupling Reactions of 6,8-Dichloropurines with Phenylboronic Acid and Methylmagnesium Chloride: Synthesis of 6,8-Di-Substituted Purines","volume":"6","author":"Hocek","year":"2004","journal-title":"Synthesis"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"15944","DOI":"10.3390\/molecules200915944","article-title":"Synthetic Routes to N-9 Alkylated 8-Oxoguanines; Weak Inhibitors of the Human DNA Glycosylase OGG1","volume":"20","author":"Mahajan","year":"2015","journal-title":"Molecules"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"44371","DOI":"10.1039\/C5RA04406E","article-title":"New Developments in Direct Functionalization of C-H and N-H Bonds of Purine Bases via Metal Catalyzed Cross-Coupling Reactions","volume":"5","author":"Abdoli","year":"2015","journal-title":"RSC Adv."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"8008","DOI":"10.1021\/acs.orglett.2c03206","article-title":"Direct Minisci-Type C-H Amidation of Purine Bases","volume":"24","author":"Mooney","year":"2022","journal-title":"Org. Lett."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"4997","DOI":"10.1039\/C3CC48642G","article-title":"Direct N9-Arylation of Purines with Aryl Halide","volume":"50","author":"Larsen","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"16","DOI":"10.1021\/acs.orglett.5b02994","article-title":"Direct, Regioselective N-Alkylation of 1,3-Azoles","volume":"18","author":"Chen","year":"2016","journal-title":"Org. Lett."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"13265","DOI":"10.1021\/acs.joc.1c01186","article-title":"Study of the N7 Regioselective Glycosylation of 6-Chloropurine and 2,6-Dichloropurine with Tin and Titanium Tetrachloride","volume":"86","year":"2021","journal-title":"J. Org. Chem."},{"key":"ref_47","first-page":"17368","article-title":"Study of Direct N7 Regioselective Tert-Alkylation of 6-Substituted Purines and Their Modification at Position C6 through O, S, N, and C Substituents","volume":"9","author":"Nevrlka","year":"2024","journal-title":"ACS Omega"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"5529","DOI":"10.1055\/a-1898-9675","article-title":"Synthesis of 7-Arylpurines from Substituted Pyrimidines","volume":"54","author":"Sebris","year":"2022","journal-title":"Synthesis"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"422","DOI":"10.1021\/acs.joc.7b02269","article-title":"One- or Two-Step Synthesis of C-8 and N-9 Substituted Purines","volume":"83","author":"Bollier","year":"2018","journal-title":"J. Org. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"364","DOI":"10.1016\/j.ejphar.2014.07.025","article-title":"Cisplatin in Cancer Therapy: Molecular Mechanisms of Action","volume":"740","author":"Dasari","year":"2014","journal-title":"Eur. J. Pharmacol."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1417","DOI":"10.1016\/0022-1902(71)80437-2","article-title":"Interaction of Metal Ions with Monosubstittuted Purines","volume":"33","author":"Krishnamoorthy","year":"1971","journal-title":"J. Inorg. Nucl. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"4929","DOI":"10.1016\/j.tet.2014.05.050","article-title":"Highly Selective Detection of Hg2+ Ion by Push-Pull-Type Purine Nucleoside-Based Fluorescent Sensor","volume":"70","author":"Gao","year":"2014","journal-title":"Tetrahedron"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"2225","DOI":"10.1002\/ejoc.201301897","article-title":"Push-Pull-Type Purine Nucleoside-Based Fluorescent Sensors for the Selective Detection of Pd2+ in Aqueous Buffer","volume":"2014","author":"Li","year":"2014","journal-title":"Eur. J. Org. Chem."},{"key":"ref_54","doi-asserted-by":"crossref","unstructured":"Chen, X., Mao, Y., Wang, A., Lu, L., Shao, Q., Jiang, C., and Lu, H. (2024). Synthesis and Application of Purine-Based Fluorescence Probe for Continuous Recognition of Cu2+ and Glyphosate. Spectrochim. Acta-Part A Mol. Biomol. Spectrosc., 304.","DOI":"10.1016\/j.saa.2023.123291"},{"key":"ref_55","doi-asserted-by":"crossref","unstructured":"Tao, X., Mao, Y., Alam, S., Wang, A., Qi, X., Zheng, S., Jiang, C., Chen, S.Y., and Lu, H. (2024). Sensitive Fluorescence Detection of Glyphosate and Glufosinate Ammonium Pesticides by Purine-Hydrazone-Cu2+ Complex. Spectrochim. Acta-Part A Mol. Biomol. Spectrosc., 314.","DOI":"10.1016\/j.saa.2024.124226"},{"key":"ref_56","doi-asserted-by":"crossref","unstructured":"Sadowska, P., Jankowski, W., Bregier-Jarz\u0119bowska, R., Pietrzyk, P., and Jastrz\u0105b, R. (2024). Deciphering the Impact of Nucleosides and Nucleotides on Copper Ion and Dopamine Coordination Dynamics. Int. J. Mol. Sci., 25.","DOI":"10.3390\/ijms25179137"},{"key":"ref_57","doi-asserted-by":"crossref","unstructured":"Schino, I., Cantore, M., de Candia, M., Altomare, C.D., Maria, C., Barros, J., Cachatra, V., Calado, P., Shimizu, K., and Freitas, A.A. (2023). Exploring Mannosylpurines as Copper Chelators and Cholinesterase Inhibitors with Potential for Alzheimer\u2019s Disease. Pharmaceuticals, 16.","DOI":"10.3390\/ph16010054"},{"key":"ref_58","doi-asserted-by":"crossref","unstructured":"Xu, H., Chen, W., Ju, L., and Lu, H. (2021). A Purine Based Fluorescent Chemosensor for the Selective and Sole Detection of Al3+ and Its Practical Applications in Test Strips and Bio-Imaging. Spectrochim. Acta-Part A Mol. Biomol. Spectrosc., 247.","DOI":"10.1016\/j.saa.2020.119074"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"26502","DOI":"10.1039\/D0CP04091F","article-title":"Proof of Principle of a Purine D-A-D\u2032 Ligand Based Ratiometric Chemical Sensor Harnessing Complexation Induced Intermolecular PET","volume":"22","author":"Jovaisaite","year":"2020","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"215047","DOI":"10.1016\/j.ccr.2023.215047","article-title":"Cyclen-Based Artificial Nucleases: Three Decades of Development (1989\u20132022). Part a\u2013Hydrolysis of Phosphate Esters","volume":"481","author":"Tomczyk","year":"2023","journal-title":"Coord. Chem. Rev."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.poly.2016.09.058","article-title":"Copper(II) Complexes of Chiral 1,2,3-Triazole Biheterocyclic \u2018Click\u2019 Ligands Equipped in Cinchona Alkaloid Moiety","volume":"121","author":"Kowalczyk","year":"2017","journal-title":"Polyhedron"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"2611","DOI":"10.1021\/ja01520a004","article-title":"Metal Complexes of Purine and Some of Its Derivatives","volume":"81","author":"Cheney","year":"1959","journal-title":"J. Am. Chem. Soc."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"23442","DOI":"10.1039\/D1RA03107D","article-title":"An Investigation of Two Copper(II) Complexes with a Triazole Derivative as a Ligand: Magnetic and Catalytic Properties","volume":"11","author":"Petrenko","year":"2021","journal-title":"RSC Adv."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"84","DOI":"10.1016\/j.jinorgbio.2015.03.006","article-title":"Lights and Shadows in the Challenge of Binding Acyclovir, a Synthetic Purine-like Nucleoside with Antiviral Activity, at an Apical-Distal Coordination Site in Copper(II)-Polyamine Chelates","volume":"148","year":"2015","journal-title":"J. Inorg. Biochem."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"92","DOI":"10.1016\/j.molstruc.2009.12.014","article-title":"Metal Ion Interactions with Nucleobases in the Tetradentate 1,4,7,10-Tetraazacyclododecane (Cyclen)-Ligand System: Crystal Structures of [Cu(Cyclen)(Adeninato)]\u00b7ClO4\u00b72H2O, [{Cu(Cyclen)}2(Hypoxanthinato)]\u00b7(ClO4)3, [Cu(Cyclen)(Theophyllinato)]3\u00b7(ClO4)3\u00b72H2O, and [Cu(cyclen)(theophyllinato)]3\u00b7(ClO4)3\u00b72H2O, and [Cu(cyclen)(xanthinato)]\u00b7(0.7ClO4)3\u00b7(0.3ClO4)3\u00b73H2O\u00b7(0.5H2O)3","volume":"966","author":"Rahman","year":"2010","journal-title":"J. Mol. Struct."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"474","DOI":"10.3762\/bjoc.15.41","article-title":"Synthesis and Fluorescent Properties of N(9)-Alkylated 2-Amino-6-Triazolylpurines and 7-Deazapurines","volume":"15","author":"Tseng","year":"2019","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"560","DOI":"10.1007\/s10593-021-02943-1","article-title":"Synthesis and Photophysical Properties of 2-Azolyl-6-Piperidinylpurines","volume":"57","author":"Sebris","year":"2021","journal-title":"Chem. Heterocycl. Compd."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"1300","DOI":"10.1002\/(SICI)1521-3773(20000403)39:7<1300::AID-ANIE1300>3.0.CO;2-I","article-title":"A G-Quartet Formed in the Absence of a Templating Metal Cation: A New 8-(N,N-Dimethylaniline)Guanosine Derivative","volume":"39","author":"Sessler","year":"2000","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1016\/j.ejmech.2013.11.036","article-title":"Structure-Based Design, Synthesis and Biological Evaluation of Diphenylmethylamine Derivatives as Novel Akt1 Inhibitors","volume":"73","author":"Liu","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"4566","DOI":"10.1021\/acs.joc.9b00442","article-title":"From Tetrahydrofurans to Tetrahydrobenzo[d]Oxepines via a Regioselective Control of Alkyne Insertion in Rhodium-Catalyzed Arylative Cyclization","volume":"84","author":"Selmani","year":"2019","journal-title":"J. Org. Chem."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"8729","DOI":"10.1002\/anie.200903923","article-title":"Synthesis of Phenol, Aromatic Ether, and Benzofuran Derivatives by Copper-Catalyzed Hydroxylation of Aryl Halides","volume":"48","author":"Zhao","year":"2009","journal-title":"Angew. Chemie-Int. Ed."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"284","DOI":"10.1021\/jo702024p","article-title":"An Improved Cu-Based Catalyst System for the Reactions of Alcohols with Aryl Halides","volume":"73","author":"Altman","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"5075","DOI":"10.1021\/jo900600m","article-title":"Copper(I)-Catalyzed Aryl Bromides to Form Intermolecular and Intramolecular Carbon-Oxygen Bonds","volume":"74","author":"Niu","year":"2009","journal-title":"J. Org. Chem."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"1116","DOI":"10.1021\/acs.joc.7b02341","article-title":"Mechanistic Studies of the Deslongchamps Annulation","volume":"83","author":"Kreibich","year":"2018","journal-title":"J. Org. Chem."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"6920","DOI":"10.1021\/ja801771u","article-title":"Rare-Earth Metal Alkyl and Hydride Complexes Stabilized by a Cyclen-Derived [NNNN] Macrocyclic Ancillary Ligand","volume":"130","author":"Ohashi","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1016\/j.cplett.2014.10.016","article-title":"Photochemistry of Copper(II) Chlorocomplexes in Acetonitrile: Trapping the Ligand-to-Metal Charge Transfer Excited Staterelaxations Pathways","volume":"615","author":"Mereshchenko","year":"2014","journal-title":"Chem. Phys. Lett."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"2729","DOI":"10.1016\/j.bmc.2019.04.024","article-title":"Design, Synthesis, and Biological Evaluation of Some Novel 4-Aminoquinazolines as Pan-PI3K Inhibitors","volume":"27","author":"Ding","year":"2019","journal-title":"Bioorg. Med. Chem."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"3656","DOI":"10.1039\/C3PY01776A","article-title":"Synthesis of a Poly(N-Isopropylacrylamide) Charm Bracelet Decorated with a Photomobile \u03b1-Cyclodextrin Charm","volume":"5","author":"Qiu","year":"2014","journal-title":"Polym. Chem."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"3247","DOI":"10.1246\/bcsj.68.3247","article-title":"Charge-Transfer Interaction and Molecular Arrangement in the Crystals of 2-(p-Nitrophenoxy)Ethyl Ethers and Amines","volume":"68","author":"Mazaki","year":"1995","journal-title":"Bull. Chem. Soc. Jpn."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/7\/1612\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T17:10:12Z","timestamp":1760029812000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/7\/1612"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,4,4]]},"references-count":79,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2025,4]]}},"alternative-id":["molecules30071612"],"URL":"https:\/\/doi.org\/10.3390\/molecules30071612","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,4,4]]}}}