Crystal structure, thermal, redox, and EPR studies of copper(II) complexes with catechol-based quaternary ammonium salts
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Bureš F. Quaternary Ammonium Compounds: Simple in Structure, Complex in Application. Top Curr Chem. 2019;377(3):14. doi:10.1007/s41061-019-0239-2
Ohno H. Functional Design of Ionic Liquids. Bull Chem Soc Japan. 2006;79(11):1665–80. doi:10.1246/bcsj.79.1665
Pârvulescu VI, Hardacre C. Catalysis in Ionic Liquids. Chem Rev. 2007;107(6):2615–65. doi:10.1021/cr050948h
Patel DD, Lee J. Applications of ionic liquids. Chem Rec. 2012;12(3):329–55. doi:10.1002/tcr.201100036
Niu H, Wang L, Guan P, Zhang N, Yan C, Ding M, Guo X, Huang T, Hu X. Recent Advances in Application of Ionic Liquids in Electrolyte of Lithium Ion Batteries. J Energy Storage. 2021;40:102659. doi:10.1016/j.est.2021.102659
Singh SK, Savoy AW. Ionic liquids synthesis and applications: An overview. J Mol Liq. 2020;297:112038. doi:10.1016/j.molliq.2019.112038
Karimi B, Tavakolian M, Akbari M, Mansouri F. Ionic Liquids in Asymmetric Synthesis: An Overall View from Reaction Media to Supported Ionic Liquid Catalysis. ChemCatChem. 2018;10(15):3173–3205. doi:10.1002/cctc.201701919
Tang B, Bi W, Tian M, Row KH. Application of ionic liquid for extraction and separation of bioactive compounds from plants. J Chromatogr B. 2012;904:1–21. doi:10.1016/j.jchromb.2012.07.020
Zhuo Y, Cheng H, Zhao Y, Cui H. Ionic Liquids in Pharmaceutical and Biomedical Applications: A Review. Pharmaceutics. 2024;16(1):151. doi:10.3390/pharmaceutics16010151
Greer AJ, Jacquemin J, Hardacre C. Industrial Applications of Ionic Liquids. Molecules. 2020;25(21):5207. doi:10.3390/molecules25215207
Plechkova NV, Seddon KR. Applications of ionic liquids in the chemical industry. Chem Soc Rev. 2008;37(1):123–50. doi:10.1039/B006677J
Encyclopedia of Ionic Liquids. Springer Nature Singapore Pte Ltd. 2022. doi:10.1007/978-981-33-4221-7
Tindale JJ, Hartlen KD, Alizadeh A, Workentin MS, Ragogna PJ. Maleimide‐Modified Phosphonium Ionic Liquids: A Template Towards (Multi)Task‐Specific Ionic Liquids. Chem – Eur J. 2010;16(30):9068–75. doi:10.1002/chem.200902610
Gélinas B, Das D, Rochefort D. Air-Stable, Self-Bleaching Electrochromic Device Based on Viologen- and Ferrocene-Containing Triflimide Redox Ionic Liquids. ACS Appl Mater Interfaces. 2017;9(34):28726–36. doi:10.1021/acsami.7b04427
Bhowmik PK, Chen SL, Han H, Ishak KA, Selvi velayutham T, Bendaoud U, Martinez-Felipe A. Dicationic ionic liquids based on bis(4-oligoethyleneoxyphenyl) viologen bistriflimide salts exhibiting high ionic conductivities. J Mol Liq. 2022;365:120126. doi:10.1016/j.molliq.2022.120126
Handa M, Almalki WH, Shukla R, Afzal O, Altamimi AS, Beg S, Rahman M. Active pharmaceutical ingredients (APIs) in ionic liquids: An effective approach for API physiochemical parameter optimization. Drug Discov Today. 2022;27(9):2415–24. doi:10.1016/j.drudis.2022.06.003
Bakulina O, Ivanov M, Alimov D, Prikhod’Ko S, Adonin N, Fedin M. Active Pharmaceutical Ingredient-Ionic Liquids (API-ILs): Nanostructure of the Glassy State Studied by Electron Paramagnetic Resonance Spectroscopy. Molecules. 2022;27(16):5117. doi:10.3390/molecules27165117
Belyakova YY, Yaremenko IA, Terent’Ev AO, Nenajdenko VG, Shambalova VE, Aldoshin AS, Krasnovskaya OO, Beloglazkina EK, Spektor DV, Machulkin AE, Averin AD, Beletskaya IP, Gromov SP, Magdesieva TV, Fomina MV, Nuriev VN, Trifonov AA, Loginov DA, Shifrina ZB, Fedorova OA, Fedotova EA, Kuzmina NS, Otvagin VF, Fedorov AY, Kalinin AA, Balakina MY, Aleksandrova YI, Shurpik DN, Stoikov II, Bazhin DN, Burgart YV, Saloutin VI, Korotaev VY, Zimnitsky NS, Ulitko MV, Sosnovskikh VY, Vasilyev AV, Volcho KP, Tikhonov AY, Shelkovnikov VV, Fisyuk AS, Kostyuchenko AS, Shatsauskas AL, Arsenyev MV, Tarakanova AE, Chesnokov SA, Klimochkin YN, Reznikov AN, Ivleva EA, Filimonov VD, Khlebnikov AI, Krasnokutskaya EA, Izmest’Ev ES, Lezina OM, Popova SA, Chukicheva IY, Musalov MV, Amosova SV, Potapov VA, Kuimov VA, Fattakhov RI, Belogorlova NA, Parshina LN, Grishchenko LA, Trofimov BA, Adamovich SN, Oborina EN, Zlotsky SS, Raskildina GZ, Sultanova RM, Aksenov AV, Aksenov DA, Aksenov NA, Shikhaliev KS, Stolpovskaya NV, Medvedeva SM, Konshina DN, Konshin VV, Vernigora AA, Burmistrov VV, Novakov IA, Kustova TP, Naumova IK, Kalmykova AA, Dyachenko IV, Dyachenko VD, Grinev VS, Krivenko AP, Yegorova AY, Dotsenko VV, Bespalov AV, Varzieva EA, Kindop VK, Akhmedov AA, Padnya PL, Shiabiev IE, Nazarova AA, Ustynyuk YA. Organic Chemistry in the Creation of Molecules with Practically Useful Properties. Russ J Gen Chem. 2026;96(1):1. doi:10.1134/S1070363225605721
Shukla MK, Tiwari H, Verma R, Dong W, Azizov S, Kumar B, Pandey S, Kumar D. Role and Recent Advancements of Ionic Liquids in Drug Delivery Systems. Pharmaceutics. 2023;15(2):702. doi:10.3390/pharmaceutics15020702
Pedro SN, Freire CS, Silvestre AJ, Freire MG. Ionic Liquids in Drug Delivery. Encyclopedia. 2021;1(2):324–39. doi:10.3390/encyclopedia1020027
Fedorova OV, Ovchinnikova IG, Rusinov GL, Avdeeva VV, Zhdanov AP, Zhizhin KY, Kuznetsov NT, Zakharova LY, Kuznetsova DA, Razuvaeva YS, Zhiltsova EP, Sinyashin OG, Alekseeva AS, Vodovozova EL, Abdrakhmanova II, Ibrahim A, Solovyeva VV, Maltsev AV, Fisenko VP, Bachurin SO, Mikhailov YM, Aleksandrova YI, Shurpik DN, Stoikov II, Ziganshina AY, Solovieva SE, Antipin IS, Agafonov MA, Terekhova IV, Ilicheva PM, Pidenko PS, Burmistrova NA, Moustafine RI, Timergalieva VR, Zabolotnaya YN, Khutoryanskiy VV, Demin AM, Levit GL, Charushin VN, Krasnov VP, Goryacheva OA, Mayorova OA, Mesheryakova SM, Goryacheva IY, Ayupova AI, Fattakhova АА, Rizvanov АА, Inozemtseva OA, Gusliakova OI, Gorin DA, Gerasimov AV, Zubaidullina LS, Ziganshin MA, Valiulin SV, Onischuk AA, Bezrukov AN, Galyametdinov YG, Padnya PL, Nazarova AA, Sultanova ED, Burilov VA. Modern Strategies of Drug Therapy: Multi-Target Drug Delivery, Bioimaging, Diagnostics. Russ J Gen Chem. 2025;95(S1):S1–S448. doi:10.1134/S1070363225606726
Nikfarjam N, Ghomi M, Agarwal T, Hassanpour M, Sharifi E, Khorsandi D, Ali khan M, Rossi F, Rossetti A, Nazarzadeh zare E, Rabiee N, Afshar D, Vosough M, Kumar maiti T, Mattoli V, Lichtfouse E, Tay FR, Makvandi P. Antimicrobial Ionic Liquid‐Based Materials for Biomedical Applications. Adv Funct Mater. 2021;31(42):2104148. doi:10.1002/adfm.202104148
Anvari S, Hajfarajollah H, Mokhtarani B, Enayati M, Sharifi A, Mirzaei M. Antibacterial and anti-adhesive properties of ionic liquids with various cationic and anionic heads toward pathogenic bacteria. J Mol Liq. 2016;221:685–90. doi:10.1016/j.molliq.2016.05.093
García MT, Bautista E, De la fuente A, Pérez L. Cholinium-Based Ionic Liquids as Promising Antimicrobial Agents in Pharmaceutical Applications: Surface Activity, Antibacterial Activity and Ecotoxicological Profile. Pharmaceutics. 2023;15(7):1806. doi:10.3390/pharmaceutics15071806
Berthod A, Ruiz-Ángel M, Carda-Broch S. Ionic liquids in separation techniques. J Chromatogr A. 2008;1184(1-2):6–18. doi:10.1016/j.chroma.2007.11.109
Branco LC, Crespo JG, Afonso CA. Highly Selective Transport of Organic Compounds by Using Supported Liquid Membranes Based on Ionic Liquids. Angew Chemie Int Ed. 2002;41(15):2771–3. doi:10.1002/1521-3773(20020802)41:15<2771::aid-anie2771>3.0.co;2-u
Han D, Row KH. Recent Applications of Ionic Liquids in Separation Technology. Molecules. 2010;15(4):2405–26. doi:10.3390/molecules15042405
Wei G, Yang Z, Chen C. Room temperature ionic liquid as a novel medium for liquid/liquid extraction of metal ions. Anal Chim Acta. 2003;488(2):183–92. doi:10.1016/S0003-2670(03)00660-3
Makanyire T, Sanchez-Segado S, Jha A. Separation and recovery of critical metal ions using ionic liquids. Adv Manuf. 2016;4(1):33–46. doi:10.1007/s40436-015-0132-3
H. davis J. Task-Specific Ionic Liquids. Chem Lett. 2004;33(9):1072–7. doi:10.1246/cl.2004.1072
Giernoth R. Task‐Specific Ionic Liquids. Angew Chemie Int Ed. 2010;49(16):2834–9. doi:10.1002/anie.200905981
Menyo MS, Hawker CJ, Waite JH. Versatile tuning of supramolecular hydrogels through metal complexation of oxidation-resistant catechol-inspired ligands. Soft Matter. 2013;9(43):10314. doi:10.1039/C3SM51824H
Yan G, Chen G, Peng Z, Shen Z, Tang X, Sun Y, Zeng X, Lin L. The Cross‐Linking Mechanism and Applications of Catechol–Metal Polymer Materials. Adv Mater Interfaces. 2021;8(19):2100239. doi:10.1002/admi.202100239
An Z, Sun J, Mei Q, Wei B, Li M, Xie J, He M, Wang Q. Unravelling the effects of complexation of transition metal ions on the hydroxylation of catechol over the whole pH region. J Environ Sci. 2022;115:392–402. doi:10.1016/j.jes.2021.08.011
Gökçe C, Gup R. Copper(II) complexes of acylhydrazones: synthesis, characterization and DNA interaction. Appl Organomet Chem. 2013;27(5):263–8. doi:10.1002/aoc.2955
Al-Ne’Aimi MM, Al-Khuder MM. Synthesis, characterization and extraction studies of some metal (II) complexes containing (hydrazoneoxime and bis-acylhydrazone) moieties. Spectrochim Acta Part A: Molecular and Biomolecular Spectroscopy. 2013;105:365–73. doi:10.1016/j.saa.2012.10.046
Gup R, Kırkan B. Synthesis and spectroscopic studies of mixed-ligand and polymeric dinuclear transition metal complexes with bis-acylhydrazone tetradentate ligands and 1,10-phenanthroline. Spectrochim Acta Part A: Molecular and Biomolecular Spectroscopy. 2006;64(3):809–15. doi:10.1016/j.saa.2005.08.008
Ahmed MA, Zhernakov MA, Gilyazetdinov EM, Bukharov MS, Islamov DR, Usachev KS, Klimovitskii AE, Serov NY, Burilov VA, Shtyrlin VG. Complexes of NiII, CoII, ZnII, and CuII with Promising Anti-Tuberculosis Drug: Solid-State Structures and DFT Calculations. Inorganics. 2023;11(4):167. doi:10.3390/inorganics11040167
Zhang Y, Yan Y, Yang R, Chen R, Dong W. Exploring the structure, fluorescence properties and theoretical studies of newly synthesized Co(II), Ni(II) and Cd(II) complexes bearing acylhydrazone ligands. J Mol Struct. 2024;1314:138840. doi:10.1016/j.molstruc.2024.138840
Mathew N, Sithambaresan M, Kurup MP. Spectral studies of copper(II) complexes of tridentate acylhydrazone ligands with heterocyclic compounds as coligands: X-ray crystal structure of one acylhydrazone copper(II) complex. Spectrochim Acta Part A: Molecular and Biomolecular Spectroscopy. 2011;79(5):1154–61. doi:10.1016/j.saa.2011.04.036
Lukov VV, Tupolova YP, Kogan VA, Popov LD. Mono- and Binuclear Copper(II) Metal Chelates with 3,5-Di(tert-butyl)salicylaldehyde Acylhydrazones. Russ J Coord Chem. 2003;29(5):335–8. doi:10.1023/A:1023675801876
Lukov VV, Knysh AA, Lyubchenko SN, Tupolova YP, Kogan VA. Physicochemical Study of New Mono- and Binuclear Copper(II) Complexes with Sterically Hindered Acylhydrazones and Azomethines. Russ J Coord Chem. 2002;28(12):874–6. doi:10.1023/A:1021642530810
Yu M, Liu X, Ren J, Liu J, Yang Z, Zhao S. Thermal properties and CT-DNA/BSA binding behavior of a binuclear Cu(II) complex with acylhydrazone containing naphthalene ring. J Coord Chem. 2018;71(7):1020–34. doi:10.1080/00958972.2018.1457145
Wu Y, Wu D, Lan J, Li A, Hou L, Xu Y, Gou Y. Assessment of Mononuclear/Dinuclear copper acylhydrazone complexes for lung cancer treatment. Bioorganic Chem. 2024;144:107122. doi:10.1016/j.bioorg.2024.107122
Santiago PH, Duarte ED, Nascimento ÉC, Martins JB, Castro MS, Gatto CC. A binuclear copper(II) complex based on hydrazone ligand: Characterization, molecular docking, and theoretical and antimicrobial investigation. Appl Organomet Chem. 2022;36(1):e6461. doi:10.1002/aoc.6461
Vrdoljak V, Pavlović G, Maltar-Strmečki N, Cindrić M. Copper(ii) hydrazone complexes with different nuclearities and geometries: synthetic methods and ligand substituent effects. New J Chem. 2016;40(11):9263–74. doi:10.1039/C6NJ01036A
Turomsha I, Gvozdev M, Khodosovskaya A, Sokolova A, Osipovich N, Ksendzova G, Koval’Chuk-Rabchinskaya T, Loginova N. Copper(II) Complexes of Hydrazone and Thiosemicarbazone Ligands: Synthesis, Characterization, Antibacterial and Antifungal Activity. Chem Porc. 2025; 18(1): 11. doi:10.3390/ecsoc-29-26698
Bulanov AO, Luk'Yanov BS, Kogan VA, Lukov VV. Bi-nuclear Copper(II) Complexes with Hydrazones Containing Spiropyran Fragment. Russ J Coord Chem. 2003;29(9):658–9. doi:10.1023/A:1025667812707
Baryshnikova SV, Arsen’Ev MV, Rumyantsev RV, Yakushev IA, Poddel’Skii AI. Copper(II) o-Iminophenolate Complexes Based on Catecholaldimines. Russ J Coord Chem. 2023;49(7):429–36. doi:10.1134/S107032842360016X
Vojinović-Ješić LS, Bogdanović GA, Leovac VM, Češljević VI, Jovanović LS. Transition metal complexes with Girard reagent-based ligands. Part IV. Synthesis and characterization of pyridoxilidene Girard-T hydrazone complexes. Crystal structure of the copper(II) complex. Struct Chem. 2008;19(5):807–15. doi:10.1007/s11224-008-9368-x
Leovac VM, Bogdanović GA, Češljević VI, Jovanović LS, Novaković SB, Vojinović-Ješić LS. Transition metal complexes with Girard reagent-based ligands. Struct Chem. 2007;18(1):113–9. doi:10.1007/s11224-006-9136-8
Sreenivasulu R, Reddy KT, Sujitha P, Kumar CG, Raju RR. Synthesis, antiproliferative and apoptosis induction potential activities of novel bis(indolyl)hydrazide-hydrazone derivatives. Bioorganic Med Chem. 2019;27(6):1043–55. doi:10.1016/j.bmc.2019.02.002
Li Y, Yan W, Yang J, Yang Z, Hu M, Bai P, Tang M, Chen L. Discovery of novel β-carboline/acylhydrazone hybrids as potent anti-tumor agents and overcome drug resistance. Eur J Med Chem. 2018;152:516–26. doi:10.1016/j.ejmech.2018.05.003
Lis C, Rubner S, Roatsch M, Berg A, Gilcrest T, Fu D, Nguyen E, Schmidt A, Krautscheid H, Meiler J, Berg T. Development of Erasin: a chromone-based STAT3 inhibitor which induces apoptosis in Erlotinib-resistant lung cancer cells. Sci Reports. 2017;7(1):17390. doi:10.1038/s41598-017-17600-x
Bonnett SA, Dennison D, Files M, Bajpai A, Parish T. A class of hydrazones are active against non-replicating Mycobacterium tuberculosis. Plos One. 2018;13(10):e0198059. doi:10.1371/journal.pone.0198059
Guilherme FD, Simonetti JÉ, Folquitto LR, Reis AC, Oliver JC, Dias AL, Dias DF, Carvalho DT, Brandão GC, Souza TB. Synthesis, chemical characterization and antimicrobial activity of new acylhydrazones derived from carbohydrates. J Mol Struct. 2019;1184:349–56. doi:10.1016/j.molstruc.2019.02.045
Reznichenko O, Quillévéré A, Martins RP, Loaëc N, Kang H, Lista MJ, Beauvineau C, González-García J, Guillot R, Voisset C, Daskalogianni C, Fåhraeus R, Teulade-Fichou M, Blondel M, Granzhan A. Novel cationic bis(acylhydrazones) as modulators of Epstein–Barr virus immune evasion acting through disruption of interaction between nucleolin and G-quadruplexes of EBNA1 mRNA. Eur J Med Chem. 2019;178:13–29. doi:10.1016/j.ejmech.2019.05.042
Dos santos filho JM, De queiroz e silva DM, Macedo TS, Teixeira HM, Moreira DR, Challal S, Wolfender J, Queiroz EF, Soares MB. Conjugation of N-acylhydrazone and 1,2,4-oxadiazole leads to the identification of active antimalarial agents. Bioorganic Med Chem. 2016;24(22):5693–5701. doi:10.1016/j.bmc.2016.09.013
Wani MY, Bhat AR, Azam A, Athar F. Nitroimidazolyl hydrazones are better amoebicides than their cyclized 1,3,4-oxadiazoline analogues: In vitro studies and Lipophilic efficiency analysis. Eur J Med Chem. 2013;64:190–9. doi:10.1016/j.ejmech.2013.03.034
Massarico serafim RA, Gonçalves JE, De souza FP, De melo loureiro AP, Storpirtis S, Krogh R, Andricopulo AD, Dias LC, Ferreira EI. Design, synthesis and biological evaluation of hybrid bioisoster derivatives of N-acylhydrazone and furoxan groups with potential and selective anti-Trypanosoma cruzi activity. Eur J Med Chem. 2014;82:418–25. doi:10.1016/j.ejmech.2014.05.077
Cerqueira JV, Meira CS, Santos ED, De aragão frança LS, Vasconcelos JF, Nonaka CK, De melo TL, Dos santos filho JM, Moreira DR, Soares MB. Anti-inflammatory activity of SintMed65, an N-acylhydrazone derivative, in a mouse model of allergic airway inflammation. Int Immunopharmacol. 2019;75:105735. doi:10.1016/j.intimp.2019.105735
Moraes AD, Miranda MD, Jacob ÍT, Amorim CA, Moura RO, Silva SÂ, Soares MB, Almeida SM, Souza TR, Oliveira JF, Silva TG, Melo CM, Moreira DR, Lima MD. Synthesis, in vitro and in vivo biological evaluation, COX-1/2 inhibition and molecular docking study of indole-N-acylhydrazone derivatives. Bioorganic Med Chem. 2018;26(20):5388–96. doi:10.1016/j.bmc.2018.07.024
Duarte CD, Tributino JL, Lacerda DI, Martins MV, Alexandre-Moreira MS, Dutra F, Bechara EJ, De-Paula FS, Goulart MO, Ferreira J, Calixto JB, Nunes MP, Bertho AL, Miranda AL, Barreiro EJ, Fraga CA. Synthesis, pharmacological evaluation and electrochemical studies of novel 6-nitro-3,4-methylenedioxyphenyl-N-acylhydrazone derivatives: Discovery of LASSBio-881, a new ligand of cannabinoid receptors. Bioorganic Med Chem. 2007;15(6):2421–33. doi:10.1016/j.bmc.2007.01.013
Zhan K, Ejima H, Yoshie N. Antioxidant and Adsorption Properties of Bioinspired Phenolic Polymers: A Comparative Study of Catechol and Gallol. ACS Sustain Chem Eng. 2016;4(7):3857–63. doi:10.1021/acssuschemeng.6b00626
Smolyaninov IV, Burmistrova DA, Arsenyev MV, Polovinkina MA, Pomortseva NP, Fukin GK, Poddel’Sky AI, Berberova NT. Synthesis and Antioxidant Activity of New Catechol Thioethers with the Methylene Linker. Molecules. 2022;27(10):3169. doi:10.3390/molecules27103169
Hasegawa U, Moriyama M, Uyama H, Van der vlies AJ. Catechol-bearing block copolymer micelles: Structural characterization and antioxidant activity. Polymer. 2015;66:1–7. doi:10.1016/j.polymer.2015.03.080
Saiz‐poseu J, Mancebo‐aracil J, Nador F, Busqué F, Ruiz‐molina D. The Chemistry behind Catechol‐Based Adhesion. Angew Chemie Int Ed. 2019;58(3):696–714. doi:10.1002/anie.201801063
Zhang W, Wang R, Sun Z, Zhu X, Zhao Q, Zhang T, Cholewinski A, Yang F(, Zhao B, Pinnaratip R, Forooshani PK, Lee BP. Catechol-functionalized hydrogels: biomimetic design, adhesion mechanism, and biomedical applications. Chem Soc Rev. 2020;49(2):433–64. doi:10.1039/C9CS00285E
Moulay S. Dopa/Catechol-Tethered Polymers: Bioadhesives and Biomimetic Adhesive Materials. Polym Rev. 2014;54(3):436–513. doi:10.1080/15583724.2014.881373
Nadagouda MN, Vijayasarathy P, Sin A, Nam H, Khan S, Parambath JB, Mohamed AA, Han C. Antimicrobial activity of quaternary ammonium salts: structure-activity relationship. Med Chem Res. 2022;31(10):1663–78. doi:10.1007/s00044-022-02924-9
Zhou Z, Zhou S, Zhang X, Zeng S, Xu Y, Nie W, Zhou Y, Xu T, Chen P. Quaternary Ammonium Salts: Insights into Synthesis and New Directions in Antibacterial Applications. Bioconjugate Chem. 2023;34(2):302–25. doi:10.1021/acs.bioconjchem.2c00598
Dan W, Gao J, Qi X, Wang J, Dai J. Antibacterial quaternary ammonium agents: Chemical diversity and biological mechanism. Eur J Med Chem. 2022;243:114765. doi:10.1016/j.ejmech.2022.114765
Bogdanov AV, Tagasheva RG, Voloshina A, Lyubina A, Tsivileva O, Kuzovlev AN, Yi W, Samorodov AV, Ziyatdinova GK, Zhiganshina ER, Arsenyev MV, Bukharov SV. Ammonium Catecholaldehydes as Multifunctional Bioactive Agents: Evaluating Antimicrobial, Antioxidant, and Antiplatelet Activity. Int J Mol Sci. 2025;26(16):7866. doi:10.3390/ijms26167866
Bogdanov AV, Bukharov SV, Garifullina RA, Voloshina AD, Lyubina AP, Amerkhanova SK, Bezsonova MS, Khaptsev ZY, Tsivileva OM. Synthesis and Antimicrobial Activity Evaluation of Ammonium Acylhydrazones Based on 4,6-Di-tert-butyl-2,3-dihydroxybenzaldehyde. Russ J Gen Chem. 2022;92(10):1875–86. doi:10.1134/S1070363222100012
Neganova M, Aleksandrova Y, Voloshina A, Lyubina A, Appazov N, Yespenbetova S, Valiullina Z, Samorodov A, Bukharov S, Gibadullina E, Tapalova A, Bogdanov A. Biological Activity Evaluation of Phenolic Isatin-3-Hydrazones Containing a Quaternary Ammonium Center of Various Structures. Int J Mol Sci. 2024;25(20):11130. doi:10.3390/ijms252011130
Bogdanov AV, Iskhakova KR, Voloshina AD, Sapunova AS, Kulik NV, Terekhova NV, Arsenyev MV, Ziyatdinova GK, Bukharov SV. Ammonium‐Charged Sterically Hindered Phenols with Antioxidant and Selective Anti‐Gram‐Positive Bacterial Activity. Chem Biodivers. 2020;17(5):e2000147. doi:10.1002/cbdv.202000147
Bogdanov AV, Samorodov AV, Valiullina ZA, Akylbekov NI, Voloshina AD, Lyubina AP, Amerkhanova SK, Saitova AM, Pashirova TN, Tsivileva OM, Mironov VF. Biologically Active Ammonium Isatin-3-acylhydrazones Bearing Long-Chain Alkyl Substituent of Various Structures. Russ J Gen Chem. 2024;94(3):539–52. doi:10.1134/S1070363224030071
Bogdanov AV, Bukharov SV, Yusupov AN, Litvinov IA, Voloshina AD, Tagasheva RG, Kolpakova EV. Ammonium acylhydrazones based on 4,6-di-tert-butyl-2,3-dihydroxybenzaldehyde: synthesis, possibilities of functionalization, and evaluation of biological activity. Russ Chem Bull. 2024;73(3):704–13. doi:10.1007/s11172-024-4181-2
Bogdanov AV, Voloshina AD, Sapunova AS, Kulik NV, Bukharov SV, Dobrynin AB, Voronina JK, Terekhova NV, Samorodov AV, Pavlov VN, Mironov VF. Isatin‐3‐acylhydrazones with Enhanced Lipophilicity: Synthesis, Antimicrobial Activity Evaluation and the Influence on Hemostasis System. Chem Biodivers. 2022;19(2):e202100496. doi:10.1002/cbdv.202100496
Bogdanov AV, Zaripova IF, Mustafina LK, Voloshina AD, Sapunova AS, Kulik NV, Mironov VF. Synthesis and Study of Antimicrobial Activity of Water-Soluble Ammonium Acylhydrazones Based on New 1,ω-Alkylenebis(isatins). Russ J Gen Chem. 2019;89(7):1368–76. doi:10.1134/S107036321907003X
Bogdanov AV, Kadomtseva ME, Bukharov SV, Voloshina AD, Mironov VF. Effect of the Cationic Moiety on the Antimicrobial Activity of Sterically Hindered Isatin 3-Hydrazone Derivatives. Russ J Org Chem. 2020;56(3):555–8. doi:10.1134/S107042802003032X
Shaihutdinova Z, Vandyukov A, Lushchekina S, Mironov V, Bukharov S, Tagasheva R, Bogdanov A, Arsenyev M, Masson P, Pashirova T. Amphiphilic ammonium acylhydrazones on the base of sterically-hindered catechol: Synthesis, self-assembly, reversible inhibition of butyrylcholinesterase and structure-activity relationships. J Mol Liq. 2025;437:128360. doi:10.1016/j.molliq.2025.128360
Moseev TD, Varaksin MV, Krinochkin AP, Valieva MA, Kudryashova EA, Sayfutdinova YM, Rybakova AV, Kopchuk DS, Zyryanov GV, Ballou Y, Slepukhin PA, Gaviko VS, Charushin VN, Chupakhin ON. Copper(II) complexes with fluorinated 5-aryl-2,2’-bipyridine-6(6’)-carboxylic acid tridentate ligands. Chim Techno Acta. 2025;12(2):12217. doi:10.15826/chimtech.2025.12.2.17
Ermolaev AV, Shtyrlin VG, Gizatullin AI, Zhernakov MA, Serov NY, Urazaeva KV, Bukharov MS, Gilyazetdinov EM, Islamov DR, Rodionov AA, Mirzayanov II, Garifzyanov AR, Kuramshin BK. Development of comprehensive approaches to characterizing CuII complexes: structures in solution and solid‐state, dynamic behavior, and bioactivity. ChemistrySelect. 2023;8(48):e202303333. doi:10.1002/slct.202303333
Krasnovskaya O, Naumov A, Guk D, Gorelkin P, Erofeev A, Beloglazkina E, Majouga A. Copper Coordination Compounds as Biologically Active Agents. Int J Mol Sci. 2020;21(11):3965. doi:10.3390/ijms21113965
Hasinoff BB, Wu X, Yadav AA, Patel D, Zhang H, Wang D, Chen Z, Yalowich JC. Cellular mechanisms of the cytotoxicity of the anticancer drug elesclomol and its complex with Cu(II). Biochem Pharmacol. 2015;93(3):266–76. doi:10.1016/j.bcp.2014.12.008
Zalevskaya OA, Gur’Eva YA. Recent Studies on the Antimicrobial Activity of Copper Complexes. Russ J Coord Chem. 2021;47(12):861–80. doi:10.1134/S1070328421120046
Rosu T, Pahontu E, Maxim C, Georgescu R, Stanica N, Gulea A. Some new Cu(II) complexes containing an ON donor Schiff base: Synthesis, characterization and antibacterial activity. Polyhedron. 2011;30(1):154–62. doi:10.1016/j.poly.2010.10.001
Weiskirchen R. Comprehensive Pharmacological Management of Wilson’s Disease: Mechanisms, Clinical Strategies, and Emerging Therapeutic Innovations. Sci. 2025;7(3):94. doi:10.3390/sci7030094
Fujisawa C, Kodama H, Sato Y, Mimaki M, Yagi M, Awano H, Matsuo M, Shintaku H, Yoshida S, Takayanagi M, Kubota M, Takahashi A, Akasaka Y. Early clinical signs and treatment of Menkes disease. Mol Genet Metab Reports. 2022;31:100849. doi:10.1016/j.ymgmr.2022.100849
Bikmukhametov A, Vasilevskaya N, Arsenyev M, Gerasimov A, Bukharov M, Islamov D, Belyakova S, Kuzin Y, Evtugyn G, Padnya P, Stoikov I. Task-specific ionic liquid and organic salts based on catechol-containing hydrazones: Synthesis, selective Cu(II) binding, thermal properties, and redox-activity. J Mol Liq. 2025;425:127234. doi:10.1016/j.molliq.2025.127234
Sheldrick GM. A short history ofSHELX. Acta Crystallogr Sect Found Crystallogr. 2008;64(1):112–22. doi:10.1107/S0108767307043930
Sheldrick G. SHELXT: Integrating space group determination and structure solution. Acta Crystallogr Sect Found Adv. 2014;70(a1):C1437–7. doi:10.1107/s2053273314085623
Macrae CF, Edgington PR, Mccabe P, Pidcock E, Shields GP, Taylor R, Towler M, Van de streek J. Mercury: visualization and analysis of crystal structures. J Appl Crystallogr. 2006;39(3):453–7. doi:10.1107/S002188980600731X
Stoll S, Schweiger A. EasySpin, a comprehensive software package for spectral simulation and analysis in EPR. J Magn Reson. 2006;178(1):42–55. doi:10.1016/j.jmr.2005.08.013
Hazra S, Martins LM, Guedes da silva MF, Pombeiro AJ. Sulfonated Schiff base copper(ii) complexes as efficient and selective catalysts in alcohol oxidation: syntheses and crystal structures. RSC Adv. 2015;5(109):90079–88. doi:10.1039/C5RA19498A
Martins NM, Mahmudov KT, Guedes da silva MF, Martins LM, Pombeiro AJ. Copper(ii) and iron(iii) complexes with arylhydrazone of ethyl 2-cyanoacetate or formazan ligands as catalysts for oxidation of alcohols. New J Chem. 2016;40(12):10071–83. doi:10.1039/C6NJ02161A
Böhme M, Mohanty M, Lima S, Buchholz A, Görls H, Dinda R, Plass W. Dinuclear Copper(II) Complex with Intramolecular O−H⋅⋅⋅O Hydrogen Bonding: Magneto‐Structural Correlation for Acylhydrazone‐Based Phenoxido Bridged Copper(II) Complexes. Eur J Inorg Chem. 2024;27(36):e202400531. doi:10.1002/ejic.202400531
Isaeva ÉL, Shamsutdinova MK, Bukov NN, Panyushkin VT. Composition and magnetic properties of a complex compound of Cu(II) with 2-[2-hydroxyphenyl]-4,4-diphenyl-1,2-dihydro-4h-3,1-benzoxazine. J Struct Chem. 2011;52(5):1037–9. doi:10.1134/s0022476611050349
Veidis MV, Schreiber GH, Gough TE, Palenik GJ. Jahn-Teller distortions in octahedral copper(II) complexes. J Am Chem Soc. 1969;91(7):1859–60. doi:10.1021/ja01035a051
Moura FD, Sobrinho YS, Stellet C, Serna JD, Ligiero CB, Yoguim MI, Cukierman DS, Diniz R, Alves OC, Morgon NH, De souza AR, Rey NA. Copper(ii) complexes of a furan-containing aroylhydrazonic ligand: syntheses, structural studies, solution chemistry and interaction with HSA. Dalton Trans. 2023;52(47):17731–46. doi:10.1039/d3dt02597g
Kawano M, Wu Y, Li Z, Mishima A, Kawata S, Ishikawa R. Magnetic superexchange couplings in doubly bis(2-pyridyl)pyrazolato-bridged dinuclear copper(ii) complexes. New J Chem. 2025;49(36):15691–9. doi:10.1039/D5NJ02006A
Rojas O, Mirzoyan G, Adamyan Z, Papoyan VV, Amatuni G, Ananikian N. Magnetic properties and entanglement in antiferromagnetic interactions in copper(II) dinuclear and trinuclear complexes. Sci Reports. 2025;15(1):11758. doi:10.1038/s41598-025-92130-5
Rodríguez MR, Balsa LM, Piro OE, Etcheverría GA, García-Tojal J, Pis-Diez R, León IE, Parajón-Costa BP, González-Baró AC. Synthesis, Crystal Structure, Spectroscopic Characterization, DFT Calculations and Cytotoxicity Assays of a New Cu(II) Complex with an Acylhydrazone Ligand Derived from Thiophene. Inorganics. 2021;9(2):9. doi:10.3390/inorganics9020009
Burgos-López Y, Balsa LM, Piro OE, León IE, García-Tojal J, Echeverría GA, González-Baró AC, Parajón-Costa BS. Tridentate acylhydrazone copper(II) complexes with heterocyclic bases as coligands. Synthesis, spectroscopic studies, crystal structure and cytotoxicity assays. Polyhedron. 2022;213:115621. doi:10.1016/j.poly.2021.115621
Kuzin YI, Guseinova A, Bikmukhametov AA, Padnya PL, Stoikov II, Porfireva AV. Electrochemical behavior of catechol-based redox-active ionic liquids and their application in electrochemical sensing of l-cysteine. Electrochimica Acta. 2026;564:148737. doi:10.1016/j.electacta.2026.148737
Jones SE, Chin DH, Sawyer DT. Redox chemistry of metal-catechol complexes in aprotic media. 2. 3,5-Di-tert-butylcatecholato complexes of manganese(IV) and manganese(III). Inorg Chem. 1981;20(12):4257–62. doi:10.1021/ic50226a045
Pashanova KI, Bitkina VO, Yakushev IA, Arsenyev MV, Piskunov AV. Square-Planar Heteroleptic Complexes of α-Diimine-NiII-Catecholate Type: Intra-molecular Ligand-to-Ligand Charge Transfer. Molecules. 2021;26(15):4622. doi:10.3390/molecules26154622
Park I, Tabelin CB, Seno K, Jeon S, Ito M, Hiroyoshi N. Simultaneous suppression of acid mine drainage formation and arsenic release by Carrier-microencapsulation using aluminum-catecholate complexes. Chemosphere. 2018;205:414–25. doi:10.1016/j.chemosphere.2018.04.088
Li X, Hiroyoshi N, Tabelin CB, Naruwa K, Harada C, Ito M. Suppressive effects of ferric-catecholate complexes on pyrite oxidation. Chemosphere. 2019;214:70–8. doi:10.1016/j.chemosphere.2018.09.086
Park I, Tabelin CB, Magaribuchi K, Seno K, Ito M, Hiroyoshi N. Suppression of the release of arsenic from arsenopyrite by carrier-microencapsulation using Ti-catechol complex. J Hazard Mater. 2018;344:322–32. doi:10.1016/j.jhazmat.2017.10.025
Pashanova KI, Ershova IV, Trofimova OY, Rumyantsev RV, Fukin GK, Bogomyakov AS, Arsenyev MV, Piskunov AV. Charge Transfer Chromophores Derived from 3d-Row Transition Metal Complexes. Molecules. 2022;27(23):8175. doi:10.3390/molecules27238175
Tembwe I, Ngila JC, Kgarebe B, Darkwa J, Iwuoha E. Electrochemical studies of the nickel catecholate complexes for detection of sulphur dioxide gas. Electrochimica Acta. 2010;55(14):4314–8. doi:10.1016/j.electacta.2009.06.081
Harmalker S, Jones SE, Sawyer DT. Electrochemical and spectroscopic studies of 3,5-di-tert-butylcatecholato and 3,5-di-tert-butyl-o-semiquinonato complexes of copper(II). Inorg Chem. 1983;22(20):2790–4. doi:10.1021/ic00162a005
Nematollahi D, Golabi S. Electrochemical study of catechol and 4-methylcatechol in methanol. Application to the electro-organic synthesis of 4,5-dimethoxy-and 4-methoxy-5-methyl-o-benzoquinone. J Electroanal Chem. 1996;405(1-2):133–40. doi:10.1016/0022-0728(95)04402-7
Mccann SD, Stahl SS. Copper-Catalyzed Aerobic Oxidations of Organic Molecules: Pathways for Two-Electron Oxidation with a Four-Electron Oxidant and a One-Electron Redox-Active Catalyst. Accounts Chem Res. 2015;48(6):1756–66. doi:10.1021/acs.accounts.5b00060
Gogoi G, Nath JK, Hoque N, Biswas S, Gour NK, Kalita DJ, Bora SR, Bania KK. Single and multiple site Cu(II) catalysts for benzyl alcohol and catechol oxidation reactions. Appl Catal A: General. 2022;644:118816. doi:10.1016/j.apcata.2022.118816
DOI: https://doi.org/10.15826/chimtech.9901
Copyright (c) 2026 Azamat Bikmukhametov, Маksim Zhernakov, Mikhail Bukharov, Yury Kuzin, Daut Islamov, Artur Khannanov, Alexander Gerasimov, Liana Zubaidullina, Alexander Rodionov, Pavel Padnya, Ivan Stoikov

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