Synthesis, biological properties, and acid dissociation constant of novel naphthoquinone–triazole hybrids

Kolb, 2001, Click chemistry: diverse chemical function from a few good reactions, Angew. Chem. Int. Ed., 40, 2004, 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5 El-Sagheer, 2010, Click chemistry with DNA, Chem. Soc. Rev., 39, 1388, 10.1039/b901971p Xu, 2019, 1,2,3-Triazole-containing hybrids as potential anticancer agents: Current developments, action mechanisms and structure-activity relationships, Eur. J. Med. Chem., 183, 10.1016/j.ejmech.2019.111700 Jiang, 2019, Recent applications of click chemistry in drug discovery, Expert Opin. Drug Discovery, 14, 779, 10.1080/17460441.2019.1614910 Rani, 2020, CuAAC-ensembled 1, 2, 3-triazole-linked isosteres as pharmacophores in drug discovery, RSC Adv., 10, 5610, 10.1039/C9RA09510A Teng, 2020, A novel series of 11-O-carbamoyl-3-O-descladinosyl clarithromycin derivatives bearing 1,2,3-triazole group: Design, synthesis and antibacterial evaluation, Bioorg. Med. Chem. Lett., 30, 10.1016/j.bmcl.2019.126850 Gao, 2019, Design, synthesis and antibacterial activity evaluation of moxifloxacin-amide-1,2,3-triazole-isatin hybrids, Bioorg. Chem., 91, 10.1016/j.bioorg.2019.103162 Nalawade, 2019, Synthesis of new thiazolyl-pyrazolyl-1,2,3-triazole derivatives as potential antimicrobial agents, Eur. J. Med. Chem., 179, 649, 10.1016/j.ejmech.2019.06.074 Tan, 2016, Synthesis, characterization, and antibacterial property of novel starch derivatives with 1, 2, 3-triazole, Carbohydr. Polym., 142, 1, 10.1016/j.carbpol.2016.01.007 Srinivasarao, 2020, Discovery of 1, 2, 3-triazole based quinoxaline-1, 4-di-N-oxide derivatives as potential anti-tubercular agents, Bioorg. Chem., 100, 10.1016/j.bioorg.2020.103955 Tan, 2018, Synthesis, characterization, and evaluation of antifungal and antioxidant properties of cationic chitosan derivative via azide-alkyne click reaction, Int. J. Biol. Macromol., 120, 318, 10.1016/j.ijbiomac.2018.08.111 Tan, 2017, Synthesis, characterization, and antifungal evaluation of novel 1, 2, 3-triazolium-functionalized starch derivative, Int. J. Biol. Macromol., 101, 845, 10.1016/j.ijbiomac.2017.03.171 González-Calderón, 2016, Antifungal activity of 1′-homo-N-1, 2, 3-triazol-bicyclic carbonucleosides: A novel type of compound afforded by azide-enolate (3+ 2) cycloaddition, Bioorg. Chem., 69, 1, 10.1016/j.bioorg.2016.09.003 Sun, 2020, Design, synthesis and structure-activity relationships of 4-phenyl-1H-1, 2, 3-triazole phenylalanine derivatives as novel HIV-1 capsid inhibitors with promising antiviral activities, Eur. J. Med. Chem., 190, 10.1016/j.ejmech.2020.112085 Manna, 2019, Anti-cancer potential of novel glycosylated 1, 4-substituted triazolylchalcone derivatives, Bioorg. Med. Chem. Lett., 29, 10.1016/j.bmcl.2019.08.019 Li, 2020, Design, synthesis and biological evaluation of homoerythrina alkaloid derivatives bearing a triazole moiety as PARP-1 inhibitors and as potential antitumor drugs, Bioorg. Chem., 94, 10.1016/j.bioorg.2019.103385 Ince, 2020, Polysubstituted pyrrolidine linked to 1,2,3-triazoles: Synthesis, crystal structure, DFT studies, acid dissociation constant, drug-likeness, and anti-proliferative activity, J. Mol. Struct., 1217, 10.1016/j.molstruc.2020.128400 Gour, 2019, Facile synthesis of 1, 2, 3-triazole-fused indolo-and pyrrolo [1, 4] diazepines, DNA-binding and evaluation of their anticancer activity, Bioorg. Chem., 93, 10.1016/j.bioorg.2019.103306 Lv, 2014, 1, 2, 3-Triazole-derived naphthalimides as a novel type of potential antimicrobial agents: Synthesis, antimicrobial activity, interaction with calf thymus DNA and human serum albumin, Bioorg. Med. Chem. Lett., 24, 308, 10.1016/j.bmcl.2013.11.013 Gup, 2017, One-pot synthesis of a new 2-substituted 1, 2, 3-triazole 1-oxide derivative from dipyridyl ketone and isonitrosoacetophenone hydrazone: Nickel (II) complex, DNA binding and cleavage properties, Bioorg. Chem., 71, 325, 10.1016/j.bioorg.2017.03.003 Narsimha, 2016, Indole-2-carboxylic acid derived mono and bis 1, 4-disubstituted 1,2,3-triazoles: synthesis, characterization and evaluation of anticancer, antibacterial, and DNA-cleavage activities, Bioorg. Med. Chem. Lett., 26, 1639, 10.1016/j.bmcl.2016.01.055 Chen, 2020, Synthesis and antioxidant activity of cationic 1, 2, 3-triazole functionalized starch derivatives, Polymers, 12, 112, 10.3390/polym12010112 Singh, 2019, A strategic approach to the synthesis of ferrocene appended chalcone linked triazole allied organosilatranes: antibacterial, antifungal, antiparasitic and antioxidant studies, Bioorgan. Med. Chem., 27, 188, 10.1016/j.bmc.2018.11.038 Tan, 2018, Synthesis and antioxidant action of chitosan derivatives with amino-containing groups via azide-alkyne click reaction and N-methylation, Carbohydr. Polym., 199, 583, 10.1016/j.carbpol.2018.07.056 Yazdani, 2019, Multi-target inhibitors against Alzheimer disease derived from 3-hydrazinyl 1, 2, 4-triazine scaffold containing pendant phenoxy methyl-1, 2, 3-triazole: Design, synthesis and biological evaluation, Bioorg. Chem., 84, 363, 10.1016/j.bioorg.2018.11.038 Macías-Rubalcava, 2014, Selected phytotoxins and organic extracts from endophytic fungus Edenia gomezpompae as light reaction of photosynthesis inhibitors, J. Photoch. Photobio. B, 138, 17, 10.1016/j.jphotobiol.2014.05.003 Aminin, 2020, 1,4-Naphthoquinones: Some biological properties and application, Chem. Pharm. Bull., 68, 46, 10.1248/cpb.c19-00911 Li, 2018, Target ROS to induce apoptosis and cell cycle arrest by 5, 7-dimethoxy-1,4-naphthoquinone derivative, Bioorg. Med. Chem. Lett., 28, 273, 10.1016/j.bmcl.2017.12.059 Gemili, 2019, Novel highly functionalized 1, 4-naphthoquinone 2-iminothiazole hybrids: synthesis, photophysical properties, crystal structure, DFT studies, and anti(myco) bacterial/antifungal activity, J. Mol. Struct., 1196, 536, 10.1016/j.molstruc.2019.06.087 A. Defant, A. Vozza, I. Mancini, Design, synthesis and antimicrobial evaluation of new norfloxacin-naphthoquinone hybrid molecules, Proceedings 41 (2019) 9. https://doi.org/10.3390/ecsoc-23-06480. Tuyun, 2019, Discovery of a new family of heterocyclic amine linked plastoquinone analogs for antimicrobial evaluation, Drug Devel. Res., 80, 1098, 10.1002/ddr.21591 Dias, 2018, Synthesis and antimicrobial evaluation of amino sugar-based naphthoquinones and isoquinoline-5, 8-diones and their halogenated compounds, Eur. J. Med. Chem., 156, 1, 10.1016/j.ejmech.2018.06.050 Janeczko, 2016, New family of antimicrobial agents derived from 1, 4-naphthoquinone, Eur. J. Med. Chem., 124, 1019, 10.1016/j.ejmech.2016.10.034 Shrestha, 2017, Synthesis and bioactivity investigation of quinone-based dimeric cationic triazolium amphiphiles selective against resistant fungal and bacterial pathogens, Eur. J. Med. Chem., 126, 696, 10.1016/j.ejmech.2016.12.008 Olawode, 2019, Synthesis and biological evaluation of 2-chloro-3-[(thiazol-2-yl) amino]-1,4-naphthoquinones, Bioorg. Med. Chem. Lett., 29, 1572, 10.1016/j.bmcl.2019.05.001 Kundu, 2020, Expeditious and eco-friendly synthesis of new multifunctionalized pyrrole derivatives and evaluation of their antioxidant property, Bioorg. Chem., 98, 10.1016/j.bioorg.2020.103734 Mathiyazhagan, 2018, Isolation of natural naphthoquinones from Juglans regia and in vitro antioxidant and cytotoxic studies of naphthoquinones and the synthetic naphthofuran derivatives, Russ. J. Bioorg. Chem., 44, 346, 10.1134/S1068162018030111 Aly, 2018, Synthesis of novel 1, 2-bis-quinolinyl-1, 4-naphthoquinones: ERK2 inhibition, cytotoxicity and molecular docking studies, Bioorg. Chem., 81, 700, 10.1016/j.bioorg.2018.09.017 Bayrak, 2017, Synthesis, computational study, and evaluation of in vitro antimicrobial, antibiofilm, and anticancer activities of new sulfanyl aminonaphthoquinone derivatives, Lett. Drug Des, Discovery, 14, 647 Kosiha, 2017, Synthesis, characterization and DNA binding/cleavage, protein binding and cytotoxicity studies of Co (II), Ni (II), Cu (II) and Zn (II) complexes of aminonaphthoquinone, J. Photoch. Photobio. B, 168, 165, 10.1016/j.jphotobiol.2017.02.010 Kosiha, 2018, Metal complexes of naphthoquinone based ligand: Synthesis, characterization, protein binding, DNA binding/cleavage and cytotoxicity studies, J. Biomol. Struct. Dyn., 36, 4170, 10.1080/07391102.2017.1413423 Gholampour, 2019, Click chemistry-assisted synthesis of novel aminonaphthoquinone-1,2,3-triazole hybrids and investigation of their cytotoxicity and cancer cell cycle alterations, Bioorg. Chem., 88, 102967, 10.1016/j.bioorg.2019.102967 Vasilevsky, 2014, Click chemistry on diterpenes: anti-inflammatory activity of the acetylenic derivatives of levopimaric acid and products of their transformations, Arkivoc, 2014, 145, 10.3998/ark.5550190.p008.471 Diogo, 2013, Synthesis and anti-Trypanosoma cruzi activity of naphthoquinone-containing triazoles: Electrochemical studies on the effects of the quinoidal moiety, Bioorgan. Med. Chem., 21, 6337, 10.1016/j.bmc.2013.08.055 T.T. Guimarães, M.D.C.F.R. Pinto, J.S. Lanza, M.N. Melo, R.L. do Monte-Neto, I.M.M. de Melo, E.B.T. Diogo, V.F. Ferreira, C.A. Camara, W.O. Valença, R.N. de Oliveira, F. Frézard, E.N. da Silva Júnior, Potent naphthoquinones against antimony-sensitive and-resistant Leishmania parasites: Synthesis of novel α-and nor-α-lapachone-based 1,2,3-triazoles by copper-catalyzed azide–alkyne cycloaddition, Eur. J. Med. Chem. 63 (2013) 523-530. https://doi.org/10.1016/j.ejmech.2013.02.038. Bala, 2014, Sequential synthesis of amino-1,4-naphthoquinone-appended triazoles and triazole-chromene hybrids and their antimycobacterial evaluation, Eur. J. Med. Chem., 85, 737, 10.1016/j.ejmech.2014.08.009 Lee, 2016, Long-life, high-rate lithium-organic batteries based on naphthoquinone derivatives, Chem. Mater., 28, 2408, 10.1021/acs.chemmater.6b00624 Gemili, 2018, Novel 1,4-naphthoquinone N-aroylthioureas: Syntheses, crystal structure, anion recognition properties, DFT studies and determination of acid dissociation constants, J. Mol. Liq., 269, 920, 10.1016/j.molliq.2018.08.054 Wang, 2014, Transition metal complexes of asymmetrical aroyl-hydrazone ligand: Syntheses, structures, DNA binding and cleavage studies, Inorg. Chim. Acta, 409, 484, 10.1016/j.ica.2013.09.001 Blois, 1958, Antioxidant determinations by the use of a stable free radical, Nature, 181, 1199, 10.1038/1811199a0 Dinis, 1994, Action of phenolic derivates (acetoaminophen, salycilate and 5-aminosalycilate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers, Arch. Biochem. Biophy., 315, 161, 10.1006/abbi.1994.1485 Nural, 2018, Green synthesis of highly functionalized octahydropyrrolo[3, 4-c]pyrrole derivatives using subcritical water, and their anti(myco)bacterial and antifungal activity, Arkivoc, 5, 51, 10.24820/ark.5550190.p010.573 Braibanti, 1987, Recommended procedure for testing the potentiometric apparatus and technique for the pH-metric measurement of metal-complex equilibrium constants, Pure Appl. Chem., 59, 1721, 10.1351/pac198759121721 Nural, 2018, Synthesis, crystal structure, DFT studies, acid dissociation constant, and antimicrobial activity of methyl 2-(4-chlorophenyl)-7a-((4-chlorophenyl)carbamothioyl)-1-oxo-5,5-diphenyl-3-thioxo-hexahydro-1H-pyrrolo[1,2-e] imidazole-6-carboxylate, J. Mol. Struct., 1160, 375, 10.1016/j.molstruc.2018.01.099 Nural, 2018, Synthesis, antimycobacterial activity, and acid dissociation constants of polyfunctionalized 3-[2-(pyrrolidin-1-yl)thiazole-5-carbonyl]-2H-chromen-2-one derivatives, Monatsh. Chem., 149, 1905, 10.1007/s00706-018-2250-7 Nural, 2018, Synthesis, antimicrobial activity and acid dissociation constants of methyl 5,5-diphenyl-1-(thiazol-2-yl) pyrrolidine-2-carboxylate derivatives, Bioorg. Med. Chem. Lett., 28, 942, 10.1016/j.bmcl.2018.01.045 Niki, 1987, Antioxidants in relation to lipid peroxidation, Chem. Phys. Lipids, 44, 227, 10.1016/0009-3084(87)90052-1 Sudan, 2014, Iron (FeII) chelation, ferric reducing antioxidant power, and immune modulating potential of Arisaema jacquemontii (Himalayan Cobra Lily), BioMed. Res. Int., 2014, 10.1155/2014/179865 Ebrahimzadeh, 2008, Iron chelating activity, phenol and flavonoid content of some medicinal plants from Iran, Afr. J. Biotechnol., 7, 3188 Aparadh, 2012, Antioxidative properties (TPC, DPPH, FRAP, metal chelating ability, reducing power and TAC) within some Cleome species, Annali di Botanica, 2, 49 Zhang, 2019, Recent development of membrane-active molecules as antibacterial agents, Eur. J. Med. Chem., 184, 10.1016/j.ejmech.2019.111743 Mazák, 2016, Advances in microspeciation of drugs and biomolecules: species-specific concentrations, acid-base properties and related parameters, J. Pharmaceut. Biomed., 130, 390, 10.1016/j.jpba.2016.03.053 Gemili, 2017, Pt (II) and Ni (II) complexes of octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea derivatives: Synthesis, characterization, physical parameters and biological activity, Inorg. Chim. Acta, 463, 88, 10.1016/j.ica.2017.04.026 Dewar, 1986, Evaluation of AM1 calculated proton affinities and deprotonation enthalpies, J. Am. Chem. Soc., 108, 8075, 10.1021/ja00285a033