Design, Synthesis, Biological Evaluation and Molecular Docking Studies of 1,4-Disubstituted 1,2,3-Triazoles: PEG-400:H₂O Mediated Click Reaction of Fluorescent Organic Probes under Ultrasonic Irradiation

References

• B. Maleki, R. Nejat, H. Alinezhad, S. M. Mousavi, B. Mahdavi, and M. Delavari, “Nanostructural Cu-Doped ZnO Hollow Spheres as an Economical and Recyclable Catalyst in the Synthesis of 1H Pyrazolo[1,2-b]Phthalazine-5,10-Diones and Pyrazolo[1,2-a][1,2,4]Triazole-1,3-Diones,”Organic Preparations and Procedures International 52, no. 4 (2020): 328–39.
   Web of Science ®Google Scholar
• B. Maleki, F. B. Tabrizy, R. Tayebee, and M. Baghayeri, “Oxidative Aromatization of 1,3,5-Trisubstituted 2-Pyrazolines Using Oxalic Acid/Sodium Nitrite System,”Polycyclic Aromatic Compounds 39, no. 2 (2019): 93–8.
   Web of Science ®Google Scholar
• B. Maleki, H. Natheghi, R. Tayebee, H. Alinezhad, A. Amiri, S. A. Hossieni, and S. M. Mahdi Nouri, “Synthesis and Characterization of Nanorod Magnetic Co–Fe Mixed Oxides and Its Catalytic Behavior towards One-Pot Synthesis of Polysubstituted Pyridine Derivatives,”Polycyclic Aromatic Compounds 40, no. 3 (2020): 633–43.
   Web of Science ®Google Scholar
• H. Alinezhad, M. Tajbakhsh, B. Maleki, and F. P. Oushibi, “Acidic Ionic Liquid [H-NP]HSO4 Promoted One-Pot Synthesis of Dihydro-1H-Indeno[1,2-b]Pyridines and Polysubstituted Imidazoles,”Polycyclic Aromatic Compounds 40, no. 5 (2020): 1485–500.
   Web of Science ®Google Scholar
• B. Maleki, O. Reiser, E. Esmaeilnezhad, and H. Jin. Choi, “SO3H-Dendrimer Functionalized Magnetic Nanoparticles (Fe3O4@D-NH-(CH2)4-SO3H): Synthesis, Characterization and Its Application as a Novel and Heterogeneous Catalyst for the One-Pot Synthesis of Polyfunctionalized Pyrans and Polyhydroquinolines,” Polyhedron 162, (2019): 129–41.
   Web of Science ®Google Scholar
• F. Adibian, A. R. Pourali, B. Maleki, M. Baghayeri, and A. Amiri, “One-Pot Synthesis of Dihydro-1H-Indeno[1,2-b] Pyridines and Tetrahydrobenzo[b] Pyran Derivatives Using a New and Efficient Nanocomposite Catalyst Based on N-Butylsulfonate-Functionalized MMWCNTs-D-NH2,” Polyhedron 175, (2020): 114179.
   Web of Science ®Google Scholar
• F. Gao, T. Wang, J. Xiao, and G. Huang, “Antibacterial Activity Study of 1,2,4-Triazole Derivatives,” European Journal of Medicinal Chemistry 173, (2019) : 274–81.
   PubMed Web of Science ®Google Scholar
• K. Bozorov, J. Zhao, H. A. Aisa. “1,2,3-Triazole-Containing Hybrids as Leads in Medicinal Chemistry: A Recent Overview,” Bioorganic & Medicinal Chemistry 27, no. 16 (2019) : 3511–31.
   PubMed Web of Science ®Google Scholar
• Z. Xu, S. J. Zhao, Y. Liu. “ 1,2,3-Triazole-containing Hybrids as Potential Anticancer Agents: Current Developments, Action Mechanisms and Structure-Activity Relationships ,” European Journal of Medicinal Chemistry 183, (2019) : 111700.
   PubMed Web of Science ®Google Scholar
• L. S. Feng, Z. Xu, L. Chang, C. Li, X. F. Yan, C. Gao, C. Ding, F. Zhao, F. Shi, and X. Wu, “Hybrid Molecules with Potential in Vitro Antiplasmodial and in Vivo Antimalarial Activity against drug-resistant Plasmodium falciparum ,” Medical Research Review 40, no. 3 (2020): 931–71.
   PubMed Web of Science ®Google Scholar
• C. P. Kaushik, J. Sangwan, R. Luxmi, K. Kumar, and A. Pahwa, “Synthetic Routes for 1,4-Disubstituted 1,2,3-Triazoles: A Review,”Current Organic Chemistry 23, no. 8 (2019): 860–900. no.
   Web of Science ®Google Scholar
• B. Zhang, “Comprehensive Review on the Anti-bacterial Activity of 1,2,3-triazole Hybrids ,” European Journal of Medicinal Chemistry 168, (2019) : 357–72.
   PubMed Web of Science ®Google Scholar
• (a) S. T. Abu-Orabi, and 1. “3-Dipolar Cycloaddition Reactions of Substituted Benzyl Azides with Acetylenic Compounds,”Molecules 7, no. 2 (2002): 302–14.
   Web of Science ®Google Scholar
  (b) W. Q. Fan, A. R. Katritzky, C. W. Rees and E. F. V. Scriven, In Comprehensive Heterocyclic Chemistry II, vol. 4. (Oxford: Elsevier Science, 1996): 1–126.
   Google Scholar
• R. B. Woodward, and R. Hoffmann, “The Conservation of Orbital Symmetry,”Angewandte Chemie International Edition in English 8, no. 11 (1969): 781–53.
   Web of Science ®Google Scholar
• (a) R. Huisgen, and 1. “3-Dipolare Cycloaddition,” Angewandte Chemie International Edition 75 , (1963) : 604–37. (b) R. Huisgen, “1,3‐Dipolar Cycloadditions. Past and Future,”Angewandte Chemie International Edition in English 2, no. 10 (1963): 565–98. (c) R. Huisgen, “Kinetics and Mechanism of 1,3‐Dipolar Cycloadditions,”Angewandte Chemie International Edition in English 2, no. 11 (1963): 633–45.
   Google Scholar
• R. Huisgen, In 1,3-Dipolar Cycloaddition Chemistry (Ed. A. Padwa), (New York: Wiley), 1 (1984): 1–176.
   Google Scholar
• (a) C. W. Tornoe, C. Christensen, and M. Meldal, “Peptidotriazoles on Solid Phase:[1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cyclo Additions of Terminal Alkynes to Azides, Journal of Organic,”Chemistry 67, no. 2002 (2002): 3057–64. (b) V. V. Rostovtsev, L. G. Green, V. V. Fokin, and K. B. Sharpless, “A Stepwise Huisgen Cycloaddition Process: Copper (I)‐Catalyzed Regio Selective “Ligation” of Azides and Terminal Alkynes,” Angewandte Chemie International Edition 41, (2002) : 2596–9.
   Google Scholar
• H. C. Kolb, M. G. Finn, and K. B. Sharpless, “Click Chemistry: Diverse Chemical Function from a Few Good Reactions,”Angewandte Chemie International Edition 40, no. 11 (2001): 2004–21.
   PubMed Web of Science ®Google Scholar
• B. List, C. F. Barbas, and R. A. Lerner, “Aldol Sensors for the Rapid Generation of Tunable Fluorescence by Antibody Catalysis,”Proceedings of the National Academy of Sciences of the United States of America 95, no. 26 (1998): 15351–5.
   PubMed Web of Science ®Google Scholar
• (a) J. P. Goddard, and J. L. Reymond, “Recent Advances in Enzyme Assays,”Trends in Biotechnology 22, no. 7 (2004): 363–70. (b) R. P. Carlson, N. Jourdain, “Fluorogenic Polypropionate Fragments for Detecting Stereoselective Aldolases,”Chemistry of Europian Journal 6, (2000): 4154–62. (c) M. K. Froemming, and D. Sames, “Fluoromorphic Substrates for Fatty Acid Metabolism: Highly Sensitive Probes for Mammalian Medium-chain acyl-CoA Dehydrogenase,”Angewandte Chemie (International ed. in English) 45, no. 4 (2006): 637–42. (d) M. K. Froemming, “Harnessing Functional Plasticity of Enzymes: A Fluorogenic Probe for Imaging 17β-HSD10 Dehydrogenase, an Enzyme Involved in Alzheimer's and Parkinson's Diseases,”Journal of the American Chemical Society 129no. 46 (2007): 14518–22. (e) B. Xing, A. Khanamiryan, and J. Rao, “Cell-Permeable near-Infrared Fluorogenic Substrates for Imaging β-Lactamase Activity,”Journal of the American Chemical Society 127, no. 12 (2005): 4158–9. (f) H. M. Guo, M. Minakawa, and F. Tanaka, “Fluorogenic Imines for Fluorescent Detection of Mannich-Type Reactions of Phenols in Water,”The Journal of Organic Chemistry 73, no. 10 (2008): 3964–6. (g) F. Tanaka, “Development of Protein, Peptide, and Small Molecule Catalysts Using Catalysis-Based Selection Strategies,”Chemical Record (New York, N.Y.) 5, no. 5 (2005): 276–85. (h) J. Gildersleeve, A. Varvak, S. Atwell, D. Evans, and P. G. Schultz, “Development of a High‐Throughput Screen for Protein Catalysts: Application to the Directed Evolution of Antibody Aldolases,”Angewandte Chemie (International ed. in English) 42, no. 48 (2003): 5971–3.
   PubMed Web of Science ®Google Scholar
• (a) F. Tanaka, R. Thayumanavan, N. Mase, and C. F. Barbas, “Rapid Analysis of Solvent Effects on Enamine Formation by Fluorescence: how Might Enzymes Facilitate Enamine Chemistry with Primary Amines,”Tetrahedron Letters 45, no. 2 (2004): 325–8. (b) N. Mase, F. Tanaka, “Rapid Fluorescent Screening for Bifunctional Amine-Acid Catalysts: Efficient Syntheses of Quaternary Carbon-Containing Aldols under Organocatalysis,”Organic Letters 5, no. 23 (2003): 4369–72. (c) N. Mase, F. Tanaka, “Synthesis of Beta-hydroxyaldehydes with Stereogenic Quaternary Carbon Centers by Direct Organocatalytic Asymmetric Aldol Reactions ,”Angewandte Chemie (International ed. in English) 43, no. 18 (2004): 2420–3.
   Web of Science ®Google Scholar
• D. J. Yee, V. Balsanek, and D. Sames, “New Tools for Molecular Imaging of Redox Metabolism: Development of a Fluorogenic Probe for 3 Alpha-Hydroxysteroid Dehydrogenases,”Journal of the American Chemical Society 126, no. 8 (2004): 2282–3.
   PubMed Web of Science ®Google Scholar
• K. E. Beatty, F. Xie, Q. Wang, and D. A. Tirrell, “Selective Dye-labeling of Newly Synthesized Proteins in Bacterial Cells ,”Journal of the American Chemical Society 127, no. 41 (2005): 14150–1.
   PubMed Web of Science ®Google Scholar
• (a) J. F. Lutz, and Z. Zarafshani, “Efficient Construction of Therapeutics, Bioconjugates, Biomaterials and Bioactive Surfaces Using Azide-Alkyne "Click" Chemistry,”Advanced Drug Delivery Reviews 60, no. 9 (2008): 958–70. (b) K. Sivakumar, F. Xie, B. M. Cash, S. Long, H. N. Barnhill, and Q. Wang, “A Fluorogenic 1,3-Dipolar Cycloaddition Reaction of 3-Azidocoumarins and Acetylenes,”Organic Letters 6, no. 24 (2004): 4603–6. (c) J. F. Lutz, “1,3-dipolar Cycloadditions of Azides and Alkynes: A Universal Ligation Tool in Polymer and Materials Science,”Angewandte Chemie (International ed. in English) 46, no. 7 (2007): 1018–25. (d) H. Nandivada, X. W. Jiang, and J. Lahann, “Click Chemistry: Versatility and Control in the Hands of Materials Scientists,” Advanced Materials 19, (2007) : 2197–08.
   PubMed Web of Science ®Google Scholar
• Z. Zhou, and C. J. Fahrni, “A Fluorogenic Probe for the copper(I)-catalyzed Azide-alkyne Ligation Reaction: Modulation of the Fluorescence Emission via 3(n,pi)-1(pi,pi) Inversion,”Journal of the American Chemical Society 126, no. 29 (2004): 8862–3.
   PubMed Web of Science ®Google Scholar
• F. Xie, K. Sivakumar, Q. B. Zeng, M. A. Bruckman, B. Hodges, and Q. Wang, “A Fluorogenic Click Reaction of Azidoanthracene Derivatives,”Tetrahedron 64, no. 13 (2008): 2906–14.
   Web of Science ®Google Scholar
• M. Sawa, T. L. Hsu, T. Itoh, M. Sugiyama, S. R. Hanson, P. K. Vogt, and C. H. Wong, “Glycoproteomic Probes for Fluorescent Imaging of Fucosylated Glycans in Vivo,”Proceedings of the National Academy of Sciences of the United States of America 103, no. 33 (2006): 12371–6.
   PubMed Web of Science ®Google Scholar
• (a) M. L. Tiku, J. B. Liesch, and F. M. Robertson, “Production of Hydrogen Peroxide by Rabbit Articular Chondrocytes. Enhancement by Cytokines,” Journal of Immunology 145, (1990) : 690–6.
   PubMed Web of Science ®Google Scholar
  (b) B. E. Bax, A. S. Alam, B. Banerji, C. M. Bax, P. J. Bevis, C. R. Stevens, B. S. Moonga, D. R. Blake, and M. Zaidi, “Stimulation of Osteoclastic Bone Resorption by Hydrogen Peroxide,”Biochemical and Biophysical Research Communications 183, no. 3 (1992): 1153–8.
   PubMed Web of Science ®Google Scholar
• (a) J. E. Kinsella, E. Frankel, B. German, J. Kanner, “Possible Mechanisms for the Protective Role of Antioxidants in Wine and Plant Foods,” Food Technology, 47 (1993) : 85–9. (b) N. Singh, and P. S. Rajini, “Free Radical Scavenging Activity of an Aqueous Extract of Potato Peel,” Food Chemistry 85, no. 4 (2004): 611–6. (c) R. L. Prior, X. Wu, and K, Schaich, “Standardized Methods for the Determination of Antioxidant Capacity and Phenolics in Foods and Dietary Supplements,”Journal of Agricultural and Food Chemistry 53, no. 10 (2005): 4290–02.
   Web of Science ®Google Scholar
• S. Trakossas, E. Coutouli-Argyropoulou, and D. J. Hadjipavlou-Litina, “Synthesis of Modified Triazole Nucleosides Possessing One or Two Base Moieties via a Click Chemistry Approach,”Tetrahedron Letters 52, no. 14 (2011): 1673–6.
   Web of Science ®Google Scholar
• (a) C. Y. Lin, A. C. Ho, H. C. Chiang, J. S. Sun, S. Y. “ Sheu, Reactive Oxygen Scavenger Effect of Pyrimidines, Benzotriazoles and Related Compounds,” Anticancer Research, and 22. (2002) : 937–42. (b) O. Bekircan, T. Ozen, N. Gumrukcuoglu, and H. Bektas, “Synthesis and Antioxidant Properties of Some New 3-(4-Chlorophenyl)-5-(Pyridin-4-yl)-4H-1,2,4-Triazole Derivatives,”Zeitschrift Fur Naturforschung 63b, (2008) : 548–54. (c) G. Aktay, B. Tozkoparan, and M. Ertan, “Investigation of Antioxidant Properties of Some 6-(alpha-aminobenzyl)thiazolo[3,2-b]-1,2,4-triazole-5-ol Compounds,”Journal of Enzyme Inhibition and Medicinal Chemistry 24, no. 3 (2009): 898–02.
   PubMedGoogle Scholar
• C. Juan-Carlos, B. Nestor-Fabian, T. Lenka-Victoria, M. Paula-Daniela, J. Hurtado, M. Macias, and J. Portilla, “Water-Compatible Synthesis of 1,2,3-Triazoles under Ultrasonic Conditions by a Cu(I) Complex-Mediated Click Reaction,”ACS Omega 5, no. 46 (2020): 30148–59.
   PubMed Web of Science ®Google Scholar
• C. W. Choi, S. C. Kim, S. S. Hwang, B. K. Choi, H. J. Ahn, M. Y. Lee, S. H. Park, and S. K. Kim, “Antioxidant Activity and Free Radical Scavenging Capacity between Korean Medicinal Plants and Flavonoids by Assay-Guided Comparison,”Plant Science 163, no. 6 (2002): 1161–8.
   Web of Science ®Google Scholar
• L. Marcocci, J. J. Maguire, M. T. Droy-Lefaix, and L. Packer, “The Nitric Oxide-Scavenging Properties of Ginkgo Biloba Extract EGb 761,”Biochemical and Biophysical Research Communications 201, no. 2 (1994): 748–55.
   PubMed Web of Science ®Google Scholar
• (a) H. Y. Wang, Y. Qin, H. Li, L. J. Roman, P. Martasek, T. L. Poulos, and R. B. Silverman, “Potent and Selective Human Neuronal Nitric Oxide Synthase Inhibition by Optimization of the 2-Aminopyridine-Based Scaffold with a Pyridine Linker,”Journal of Medicinal Chemistry 59, no. 10 (2016): 4913–25. (b) J. P. Declercq, C. Evrard, A. Clippe, D. V. Stricht, A. Bernard, and B. K. Declercq, “Crystal Structure of Human Peroxiredoxin 5, A Novel Type of Mammalian Peroxiredoxin at 1.5 Å Resolution,”Journal of Molecular Biology 311 (2001): 751–59.
   PubMed Web of Science ®Google Scholar
• J. M. Wang, C. Jun, K. Chai, K. Kwak, and Z. S. Quan, “Synthesis and Anticonvulsant Activity of 1-Substituted benzyl-N-Substituted-1,2,3-Triazole-4-Formamides,” Progress in Natural Science 16, (2006) : 925–9.
   Web of Science ®Google Scholar
• (a) B. Vishnu Nayak, S. Ciftci-Yabanoglu, S. S. Jadav, M. Jagrat, B. N. Sinha, G. Ucar, and V. Jayaprakash, “Monoamine Oxidase Inhibitory Activity of 3, 5-Biaryl-4, 5-Dihydro-1H-Pyrazole-1-Carboxylate Derivatives, Europian,”Journal of Medicinal Chemistry 69 (2013) : 762–7. (b) B. Vishnu Nayak, I. Baysal, G. Ucar, B. N. Sinha, “Monoamine Oxidase Inhibitory Activity of Novel Pyrazoline Analogues: curcumin Based Design and Synthesis,” ACS Medicinal Chemistry Letters 7, (2015): 56–61. (c) B. Vishnu Nayak, S. Ciftci-Yabanoglu, S. Bhakat, T. Ajay Kumar, B. N. Sinha, G. Ucar, M. E. S. Soliman, and V. Jayaprakash, “ Monoamine Oxidase Inhibitory Activity of 2-Aryl-4H-Chromen-4-Ones,” Bioorganic Chemistry 58, (2005) : 72–80.
   Web of Science ®Google Scholar