New Tetrapodal Pyrazole-Tetrazole Ligands: Synthesis, Characterization, and Evaluation of the Antibacterial Activity

References

• J.V. Faria, P.F. Vegi, A.G.C. Miguita, M.S. Dos Santos, N. Boechat, and A.M.R. Bernardino, “Recently Reported Biological Activities of Pyrazole Compounds,” Bioorganic & Medicinal Chemistry 25, no. 21 (2017): 5891–903.
   PubMed Web of Science ®Google Scholar
• A.A. Bekhit, and T. Abdel-Aziem, “Design, Synthesis and Biological Evaluation of Some Pyrazole Derivatives as anti-Inflammatory-Antimicrobial Agents,” Bioorganic & Medicinal Chemistry 12, no. 8 (2004): 1935–45.
   PubMed Web of Science ®Google Scholar
• G.S. Hassan, D.E. Abdel Rahman, E.A. Abdelmajeed, R.H. Refaey, M. Alaraby Salem, and Y.M. Nissan, “New Pyrazole Derivatives: Synthesis, Anti-Inflammatory Activity, Cycloxygenase Inhibition Assay and Evaluation of mPGES,” European Journal of Medicinal Chemistry 171 (2019): 332–42.
   PubMed Web of Science ®Google Scholar
• G. Yang, H. Zheng, W. Shao, L. Liu, and Z. Wu, “Study of the In Vivo Antiviral Activity against TMV Treated with Novel 1-(t-Butyl)-5-Amino-4-Pyrazole Derivatives Containing a 1, 3, 4-Oxadiazole Sulfide Moiety,” Pesticide Biochemistry and Physiology 171 (2021): 104740.
   PubMed Web of Science ®Google Scholar
• H. Dai, S. Ge, J. Guo, S. Chen, M. Huang, J. Yang, S. Sun, Y. Ling, and Y. Shi, “Development of Novel Bis-Pyrazole Derivatives as Antitumor Agents with Potent Apoptosis Induction Effects and DNA Damage,” European Journal of Medicinal Chemistry 143 (2018): 1066–76.
   PubMed Web of Science ®Google Scholar
• B. Kupcewicz, K. Sobiesiak, K. Malinowska, K. Koprowska, M. Czyz, B. Keppler, and E. Budzisz, “Copper (II) Complexes with Derivatives of Pyrazole as Potential Antioxidant Enzyme Mimics,” Medicinal Chemistry Research 22, no. 5 (2013): 2395–402.
   PubMed Web of Science ®Google Scholar
• T. Harit, M. Cherfi, H. Abouloifa, J. Isaad, I. Bouabdallah, M. Rahal, A. Asehraou, and F. Malek, “Synthesis, Characterization, Antibacterial Properties and DFT Studies of Two New Polypyrazolic Macrocycles,” Polycyclic Aromatic Compounds 40, no. 5 (2020): 1459–69.
   Web of Science ®Google Scholar
• T. Harit, and F. Malek, “New Polymeric Membrane Incorporating a Tetrapyrazolic Macrocycle for the Selective Transport of Cesium Cation,” Separation and Purification Technology 176 (2017): 8–14.
   Web of Science ®Google Scholar
• T. Harit, R. Bellaouchi, C. Mokhtari, B.El. Bali, A. Asehraou, and F. Malek, “New Generation of Tetrapyrazolic Macrocycles: Synthesis and Examination of Their Complexation Properties and Antibacterial Activity,” Tetrahedron 73, no. 34 (2017): 5138–43.
   Web of Science ®Google Scholar
• M. Dahmani, T. Harit, A. Et-Touhami, A. Yahyi, D. Eddike, M. Tillard, and R. Benabbes, “Two Novel Macrocyclic Organotin (IV) Carboxylates Based on Bipyrazoledicarboxylic Acid Derivatives: Syntheses, Crystal Structures and Antifungal Activities,” Journal of Organometallic Chemistry 948 (2021): 121913.
   Web of Science ®Google Scholar
• F. Malek, T. Harit, M. Cherfi, and B. Kim, “Insights on the Synthesis of N-Heterocycles Containing Macrocycles and Their Complexion and Biological Properties,” Molecules 27, no. 7 (2022): 2123.
   PubMed Web of Science ®Google Scholar
• T. Harit, F. Malek, B.El. Bali, A. Khan, K. Dalvandi, B.P. Marasini, S. Noreen, R. Malik, S. Khan, and M.I. Choudhary, “Synthesis and Enzyme Inhibitory Activities of Some New Pyrazole-Based Heterocyclic Compounds,” Medicinal Chemistry Research 21, no. 10 (2012): 2772–8.
   Web of Science ®Google Scholar
• F. Malek, N. Draoui, O. Feron, and S. Radi, “Tridentate Bipyrazole Compounds with a Side-Arm as a New Class of Antitumor Agents,” Research on Chemical Intermediates 40, no. 2 (2014): 681–7.
   Web of Science ®Google Scholar
• T. Harit, H. Abouloifa, M. Tillard, D. Eddike, A. Asehraou, and F. Malek, “New Copper Complexes with Bipyrazolic Ligands: Synthesis, Characterization and Evaluation of the Antibacterial and Catalytic Properties,” Journal of Molecular Structure 1163 (2018): 300–7.
   Web of Science ®Google Scholar
• M. Dahmani, A. Et-Touhami, A. Yahyi, T. Harit, D. Eddike, M. Tillard, and R. Benabbes, “Synthesis, Characterization, X-Ray Structure and In Vitro Antifungal Activity of Triphenyltin Complexes Based on Pyrazole Dicarboxylic Acid Derivatives,” Journal of Molecular Structure 1225 (2021): 129137.
   Web of Science ®Google Scholar
• S. Leyva-Ramos, and J. Cardoso-Ortiz, “Recent Developments in the Synthesis of Tetrazoles and Their Pharmacological Relevance,” Current Organic Chemistry 25, no. 3 (2021): 388–403.
   Web of Science ®Google Scholar
• Y. Allab, S. Chikhi, S. Zaater, M. Brahimi, and S. Djebbar, “Impact of the Functionalized Tetrazole Ring on the Electrochemical Behavior and Biological Activities of Novel Nickel (II) Complexes with a Series of Tetrazole Derivatives,” Inorganica Chimica Acta 504 (2020): 119436.
   Web of Science ®Google Scholar
• S.Q. Wang, Y.F. Wang, and Z. Xu, “Tetrazole Hybrids and Their Antifungal Activities,” European Journal of Medicinal Chemistry 170 (2019): 225–34.
   PubMed Web of Science ®Google Scholar
• S. Sharma, K.A. Kozek, K.K. Abney, S. Kumar, N. Gautam, Y. Alnouti, C.David. Weaver, and C.R. Hopkins, “Discovery, Synthesis and Characterization of a Series of (1-Alkyl-3-Methyl-1H-Pyrazol-5-yl)-2-(5-Aryl-2H-Tetrazol-2-yl) Acetamides as Novel GIRK1/2 Potassium Channel Activators,” Bioorganic & Medicinal Chemistry Letters 29, no. 6 (2019): 791–6.
   PubMed Web of Science ®Google Scholar
• P.P. Kattimani, S.M. Somagond, P.K. Bayannavar, R.R. Kamble, S.C. Bijjaragi, R.K. Hunnur, and S.D. Joshi, “Novel 5‐(1‐Aryl‐1H‐Pyrazol‐3‐yl)‐1H‐Tetrazoles as Glycogen Phosphorylase Inhibitors: An In Vivo Antihyperglycemic Activity Study,” Drug Development Research 81, no. 1 (2020): 70–84. no(202).
   PubMed Web of Science ®Google Scholar
• S.A. Rostom, H.M. Ashour, H.A. Abd El Razik, A.H. Abd El Fattah, and N.N. El-Din, “Azole Antimicrobial Pharmacophore-Based Tetrazoles: Synthesis and Biological Evaluation as Potential Antimicrobial and Anticonvulsant Agents,” Bioorganic & Medicinal Chemistry 17, no. 6 (2009): 2410–22.
   PubMed Web of Science ®Google Scholar
• C.X. Wei, M. Bian, and G.H. Gong, “Tetrazolium Compounds: Synthesis and Applications in Medicine,” Molecules (Basel, Switzerland) 20, no. 4 (2015): 5528–53.
   PubMed Web of Science ®Google Scholar
• A.M. Young, K.L. Audus, J. Proudfoot, and M. Yazdanian, “Tetrazole Compounds: The Effect of Structure and pH on Caco-2 Cell Permeability,” Journal of Pharmaceutical Sciences 95, no. 4 (2006): 717–25.
   PubMed Web of Science ®Google Scholar
• L.V. Myznikov, A. Hrabalek, and G.I. Koldobskii, “Drugs in the Tetrazole Series,” Chemistry of Heterocyclic Compounds 43, no. 1 (2007): 1–9.
   Google Scholar
• D.R. Martins, F. Pazini, V. de Medeiros Alves, S.S. de Moura, L.M. Lião, M.T.Q. de Magalhães, M.C. Valadares, C.H. Andrade, R. Menegatti, and M.L. Rocha, “Synthesis, Docking Studies, Pharmacological Activity and Toxicity of a Novel Pyrazole Derivative (LQFM 021)—Possible Effects on Phosphodiesterase,” Chemical & Pharmaceutical Bulletin 61, no. 5 (2013): 524–31.
   PubMed Web of Science ®Google Scholar
• Mahadev N. Kumbar, Ravindra R. Kamble, Jagadeesh Prasad Dasappa, Praveen K. Bayannavar, Hussien Ahmed Khamees, M. Mahendra, Shrinivas D. Joshi, Suneel Dodamani, V.P. Rasal, and Sunil Jalalpure, “5-(1-Aryl-3-(Thiophen-2-yl)-1H-Pyrazol-4-yl)-1H-Tetrazoles: Synthesis, Structural Characterization, Hirshfeld Analysis, anti-Inflammatory and anti-Bacterial Studies,” Journal of Molecular Structure 1160 (2018): 63–72.
   Web of Science ®Google Scholar
• N. Kaushik, N. Kumar, and A. Kumar, “Synthesis, Antioxidant and Antidiabetic Activity of 1-[(5-Substituted Phenyl)-4, 5-Dihydro-1H-Pyrazol-3-yl]-5-Phenyl-1H-Tetrazole,” Indian Journal of Pharmaceutical Sciences 78, no. 3 (2016): 352–9.
   Web of Science ®Google Scholar
• M. Cherfi, I. Dib, T. Harit, A. Ziyyat, and F. Malek, “Synthesis and Characterization of New Pyrazole-Tetrazole Derivatives as New Vasorelaxant Agents," Drug Development Research 82, no. 7 (2021): 1055–62.
   PubMed Web of Science ®Google Scholar
• M. Cherfi, T. Harit, M.I. Yahyaoui, A. Riahi, A. Asehraou, and F. Malek, “Synthesis, Antimicrobial Activity and In-Silico Docking of Two Macrocycles Based on Pyrazole-Tetrazole Subunit,” Journal of Molecular Structure 1261 (2022): 132947.
   Web of Science ®Google Scholar
• A. Oulous, N.E. Daoudi, T. Harit, M. Cherfi, M. Bnouham, and F. Malek, “New Pyrazole-Tetrazole Hybrid Compounds as Potent α-Amylase and Non-Enzymatic Glycation Inhibitors,” Bioorganic & Medicinal Chemistry Letters 69 (2022): 128785.
   PubMed Web of Science ®Google Scholar
• G. Tarrago, A. Ramdani, J. Elguero, and M. Espada, “Orientation de la réaction d'alkylation des pyrazoles dans des conditions neutres et en catalyse par transfert de phase,” Journal of Heterocyclic Chemistry 17, no. 1 (1980): 137–42.
   Web of Science ®Google Scholar
• T. Harit, R. Bellaouchi, Y. Rokni, A. Riahi, F. Malek, and A. Asehraou, “Synthesis, Characterization, Antimicrobial Activity, and Docking Studies of New Triazolic Tripodal Ligands,” Chemistry & Biodiversity 14, no. 12 (2017): e1700351.
   Web of Science ®Google Scholar
• J. Elguero, and R. Jacquier, “Recherches dans la série des azoles-VII—Attribution des signaux RMN de pyrazoles N-substitués,” Journal de Chimie Physique 63 (1966): 1242–6.
   Google Scholar
• T. Harit, F. Malek, and B. Ameduri, “Fluorinated Polymers Based on Pyrazole Groups for Fuel Cell Membranes,” European Polymer Journal 79 (2016): 72–81.
   Web of Science ®Google Scholar
• S.J. Wittenberger, “Recent Development in Tetrazole Chemistry. A Review,” Organic Preparations and Procedures International 26, no. 5 (1994): 499–531.
   Web of Science ®Google Scholar
• J.V. Duncia, M.E. Pierce, and J.B. Santella, “Three Synthetic Routes to a Sterically Hindered Tetrazole. A New One-Step Mild Conversion of an Amide into a Tetrazole,” The Journal of Organic Chemistry 56, no. 7 (1991): 2395–400.
   Web of Science ®Google Scholar
• D.P. Curran, S. Hadida, and S.Y. Kim, “Tris (2-Perfluorohexylethyl) Tin Azide: A New Reagent for Preparation of 5-Substituted Tetrazoles from Nitriles with Purification by Fluorous/Organic Liquid-Liquid Extraction,” Tetrahedron 55, no. 29 (1999): 8997–9006.
   Web of Science ®Google Scholar
• J.H. Nelson, D.L. Schmitt, R.A. Henry, D.W. Moore, and H.B. Jonassen, “Platinum-and Palladium-Tetrazole Complexes,” Inorganic Chemistry 9, no. 12 (1970): 2678–81.
   Web of Science ®Google Scholar
• S. Achamlale, A. Elachqar, A.El. Hallaoui, A. Alami, S. Elhajji, M.L. Roumestant, and P. Viallefont, “Synthesis of Biheterocyclicα-Amino Acids,” Amino Acids 17, no. 2 (1999): 149–63.
   PubMed Web of Science ®Google Scholar
• N. Sadlej-Sosnowska, “Application of Natural Bond Orbital Analysis to Delocalization and Aromaticity in C-Substituted Tetrazoles,” The Journal of Organic Chemistry 66, no. 26 (2001): 8737–43.
   PubMed Web of Science ®Google Scholar
• V.A. Ostrovskii, and A. O. Koren, “Alkylation and Related Electrophilic Reactions at Endocyclic Nitrogen Atoms in the Chemistry of Tetrazoles,” Heterocycles 53, no. 6 (2000): 1421–48.
   Web of Science ®Google Scholar
• J. Gaire, J. McGinley, A. Fleming, and F. Kelleher, “Synthesis and Characterisation of Macromolecules Containing Multiple Tetrazole Functionalities,” Tetrahedron 68, no. 29 (2012): 5935–41.
   Web of Science ®Google Scholar
• T. Harit, B. Ameduri, and F. Malek, “Synthesis and Characterization of New Fluorinated Copolymers Based on Azole Groups for Fuel Cell Membranes,” Solid State Ionics. 317 (2018): 108–14.
   Web of Science ®Google Scholar
• F. Himo, Z.P. Demko, L. Noodleman, and K.B. Sharpless, “Why Is Tetrazole Formation by Addition of Azide to Organic Nitriles Catalyzed by Zinc (II) Salts?,” Journal of the American Chemical Society 125, no. 33 (2003): 9983–7.
   PubMed Web of Science ®Google Scholar
• M. Balouiri, M. Sadiki, and S.K. Ibnsouda, “Methods for In Vitro Evaluating Antimicrobial Activity: A Review,” Journal of Pharmaceutical Analysis 6, no. 2 (2016): 71–9.
   PubMed Web of Science ®Google Scholar