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Research Articles

Synthesis and Biological Activity Investigation of New Oxazolopyrimidoazepine Derivatives: Application of Ag/Fe3O4/TiO2/CuO@MWCNTs MNCs in the Reduction of Organic Pollutants

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Pages 5996-6017 | Received 04 Mar 2022, Accepted 29 Jul 2022, Published online: 22 Aug 2022

References

  • A. Domling, “Recent Developments in Isocyanide Based Multicomponent Reactions in Applied Chemistry,” Chemical Reviews 106 (2006): 17.
  • L.F. Tietze, and N.N. Rackelmann, “Domino reactions in the synthesis of heterocyclic natural products and analogs,” Pure and Applied Chemistry 11 (2004): 1967.
  • A. Domling, and I. Ugi, “Multicomponent Reactions with Isocyanides,” Angewandte Chemie 39, no. 18 (2000): 3168–210.
  • J. Kolb, B. Beck, M. Almstetter, S. Heck, E. Herdtweck, and A. Domling, “New MCRs: The First 4-Component Reaction Leading to 2,4-Disubstituted Thiazoles,” Molecular Diversity 6, no. 3–4 (2003): 297–313.
  • A. Domling, I. Ugi, and B. Werner, “The Chemistry of Isocyanides, Their Multicomponent Reactions and Their Libraries,” Molecules 8, no. 1 (2003): 53–66.
  • R.S. Bon, B.V. Vliet, N.E. Sprenkels, R.F. Schmitz, F.J.J. Kanter, C.V. Stevens, M. Swart, F.M. Bickelhaupt, M.B. Groen, and R.V. Orru, “Multicomponent Synthesis of 2-Imidazolines,” The Journal of Organic Chemistry 70, no. 9 (2005): 3542–53.
  • Luca Banfi, Andrea Basso, Giuseppe Guanti, Nicola Kielland, Claudio Repetto, and Renata Riva, “Ugi Multicomponent Reaction Followed by an Intramolecular Nucleophilic Substitution: Convergent Multicomponent Synthesis of 1-Sulfonyl 1,4-Diazepan-5-Ones and of Their Benzo-Fused Derivatives,” The Journal of Organic Chemistry 72, no. 6 (2007): 2151–60.
  • C.V. Galliford, and K.A. Scheidt, “Catalytic Multicomponent Reactions for the Synthesis of N-Aryl Trisubstituted Pyrroles,” The Journal of Organic Chemistry 72, no. 5 (2007): 1811–3.
  • C. Szántay, H. Bölcskei, and E. Gács-Baitz, “Synthesis of Vinca Alkaloids and Related Compounds XLVIII Synthesis of (+)-Catharanthine and (±)-Allocatharanthine,” Tetrahedron 46, no. 5 (1990): 1711–32.
  • S. Loison, M. Cottet, H. Orcel, H. Adihou, R. Rahmeh, L. Lamarque, E. Trinquet, E. Kellenberger, M. Hibert, T. Durroux, “Determination of ligand binding using flow cytometry,” Journal of Medicinal Chemistry 21 (1978): 1105.
  • (a) A. Aoyama, K. Endo-Umeda, K. Kishida, K. Ohgane, T. Noguchi-Yachide, H. Aoyama, M. Ishikawa, H. Miyachi, M. Makishima, Y. Hashimoto, “Design, Synthesis, and Biological Evaluation of Novel Transrepression-Selective Liver X Receptor (LXR) Ligands with 5,11-Dihydro-5-Methyl-11-Methylene-6H-Dibenz[b,e]Azepin-6-One Skeleton,” Journal of Medicinal Chemistry 55, no. 17 (2012): 7360–77. (b) E. Acques, and G. Di Chiara. “Local application of SCH 39166 reversibly and dose-dependently decreases acetylcholine release in the rat striatum,” European Journal of Pharmacology 383 (1999): 275.
  • A. Rosowsky, V. Cody, N. Galitsky, H. Fu, A.T. Papoulis, and S.F. Queener, “Structure-Based Design of Selective Inhibitors of Dihydrofolate Reductase: Synthesis and Antiparasitic Activity of 2, 4-Diaminopteridine Analogues with a Bridged Diarylamine Side Chain,” Journal of Medicinal Chemistry 42, no. 23 (1999): 4853–60.
  • I. Akritopoulou-Zanze, W. Braje, S.W. Djuric, N.S. Wilson, S.C. Turner, A.W. Kruger, A.L. Relo, S. Shekhar, D.S. Welch, and H.Y. Zhao, US Patent Appl. Publ. US 20110118231 A1 20110519, 2011; Chemical Abstracts 154 (2011): 615137.
  • A.K. Jain, N.S. Thomas, and R. Panchaqnula, “Transdermal Drug Delivery of Imipramine Hydrochloride. I. Effect of Terpenes,” Journal of Controlled Release 79, no. 1–3 (2002): 93–101.
  • J.W. Watthey, J.L. Stanton, M. Desai, J.E. Babiarz, and B.M. Finn, “Synthesis and Biological Properties of (Carboxyalkyl)Amino-Substituted Bicyclic Lactam Inhibitors of Angiotensin Converting Enzyme,” Journal of Medicinal Chemistry 28, no. 10 (1985): 1511–6.
  • Y.L. Zhong, B. Pipik, J. Lee, Y. Kohmura, S. Okada, K. Igawa, C. Kadowaki, A. Takezawa, S. Kato, D.A. Conlon, et al., “Practical Synthesis of a HIV Integrase Inhibitor,” Organic Process Research & Development 12, no. 6 (2008): 1245–52.
  • T. Ikemoto, T. Ito, A. Nishiguchi, S. Miura, and K. Tomimatsu, “Practical Synthesis of an Orally Active CCR5 Antagonist, 7-{4-[2-(Butoxy)-Ethoxy]Phenyl}-N-(4-{[Methyl(Tetrahydro-2H-Pyran-4-yl)Amino]Methyl}Phenyl)-1-Propyl-2,3-Dihydro-1 H-1-Benzazepine-4-Carboxamide,” Organic Process Research & Development 9, no. 2 (2005): 168–73.
  • A.A. Protter, and S. Chakravarty, Patent WO 2012112961 A1, 2012; Chemical Abstracts 157 (2012): 400665.
  • D.J. Brown, R.F. Evans, W.B. Cowden, and M.D. Fenn, The Chemistry of Heterocyclic Compounds, Vol. 52, ed. E.C. Taylor (Wiley: New York, 1994), 49–238.
  • K.S. Jain, T.S. Chitre, P.B. Miniyar, M.K. Kathiravan, V.S. Bendre, V.S. Veer, S.H. Shahane, and C.J. Shishoo, “Biological and medicinal significance of pyrimidines,” Current Science 90 (2006): 793–803.
  • L.M. Acosta, J. Jurado, A. Palma, J. Cobo, and C. Glidewell, “Six polycyclic pyrimidoazepine derivatives: syntheses, molecular structures and supramolecular assembly,” Acta Crystallographica C71 (2015): 1062–8.
  • J.-P. Bouillon, V. Bouillon, C. Wynants, Z. Janousek, and H.G. Viehe, “Trifluoromethylated Pyrimidines Starting from β-Trifluoroacetyl-lactams, -lactone and -cyclanone,” Heterocycles 37 (1994): 915–32.
  • D. Tsvelikhovsky, and S.L. Buchwald, “Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2-chloro-N-(2-Vinyl)Aniline: Preparation of Carbazoles, Indoles, Dibenzazepines, and Acridines,” Journal of the American Chemical Society 132, no. 40 (2010): 14048–51.
  • R. Vardanyan, and V. Hruby, Synthesis of Essential Drugs (Amsterdam: Elsevier, 2006), 103–16.
  • J. Benes, A. Parada, A.A. Figueiredo, P.C. Alves, A.P. Freitas, D.A. Learmonth, R.A. Cunha, J. Garrett, and P. Soares-da-Silva, “Anticonvulsant and Sodium Channel-Blocking Properties of Novel 10,11-Dihydro-5H-Dibenz[b,f]Azepine-5-Carboxamide Derivatives,” Journal of Medicinal Chemistry 42, no. 14 (1999): 2582–7.
  • R. Sahay, J. Sundaramurthy, P. Suresh Kumar, V. Thavasi, S.G. Mhaisalkar, and S. Ramakrishna, “Synthesis and Characterization of CuO Nanofibers, and Investigation for Its Suitability as Blocking Layer in ZnO NPs Based Dye Sensitized Solar Cell and as Photocatalyst in Organic Dye Degradation,” Journal of Solid State Chemistry 186 (2012): 261–7.
  • Y. Yang, B. Xu, J. He, J. Shi, L. Yu, and Y. Fan, “Magnetically separable mesoporous silica-supported palladium nanoparticle-catalyzed selective hydrogenation of naphthalene to tetralin,” Applied Organometallic Chemistry 33 (2019): e5204.
  • Y. Zhao, L. Xu, Ch Yang, T. Chen, and L. Yu, “Design and preparation of magnetic mesoporous melamine–formaldehyde resin: A novel material for pre-concentration and determination of silver,” Applied Organometallic Chemistry 33 (2019): e5112.
  • Y. Yang, B. Xu, J. He, J. Shi, L. Yu, and Y. Fan, “Design and Synthesis of Fe3O4@SiO2@mSiO2-Fe: A Magnetically Separable Catalyst for Selective Oxidative Cracking Reaction of Styrene Using Air as Partial Oxidant,” Applied Catalysis A: General 590 (2020): 117353.
  • X. Chen, J. Mao, C. Liu, C. Chen, H. Cao, and L. Yu, “An Unexpected Generation of Magnetically Separable Se/Fe3O4 for Catalytic Degradation of Polyene Contaminants with Molecular Oxygen,” Chinese Chemical Letters 31, no. 12 (2020): 3205–8.
  • B.-T. Zhang, X. Zheng, H.-F. Li, and J.-M. Lin, “Application of Carbon-Based Nanomaterials in Sample Preparation: A Review,” Analytica Chimica Acta 784 (2013): 1–17.
  • I.E. Wachs, “Recent Conceptual Advances in the Catalysis Science of Mixed Metal Oxide Catalytic Materials,” Catalysis Today 100, no. 1–2 (2005): 79–94.
  • Z. Guo, B. Liu, Q. Zhang, W. Deng, Y. Wang, and Y. Yang, “Recent Advances in Heterogeneous Selective Oxidation Catalysis for Sustainable Chemistry,” Chemical Society Reviews 43, no. 10 (2014): 3480–524.
  • Arif Daştan, Aditya Kulkarni, and Béla Török, “Environmentally Benign Synthesis of Heterocyclic Compounds by Combined Microwave-Assisted Heterogeneous Catalytic Approaches,” Green Chemistry 14, no. 1 (2012): 17–37.
  • Magdalena Jabłońska, and Regina Palkovits, “Nitrogen Oxide Removal over Hydrotalcite-Derived Mixed Metal Oxides,” Catalysis Science & Technology 6, no. 1 (2016): 49–72.
  • J. Shi, “On the Synergetic Catalytic Effect in Heterogeneous Nanocomposite Catalysts,” Chemical Reviews 113, no. 3 (2013): 2139–81.
  • S. Lin-Bing, L. Xiao-Qin, and Z. Hong-Cai, “Design and fabrication of mesoporous heterogeneous basic catalysts,” Chemical Society Reviews 44 (2015): 5092–147.
  • Q. Zhang, K.D.V. Vigier, S. Royer, and F. Jerome, “Deep Eutectic Solvents: Syntheses, Properties and Applications,” Chemical Society Reviews 41, no. 21 (2012): 7108–46.
  • E. Kalantari, M.A. Khalilzadeh, D. Zareyee, and M. Shokouhimehr, “Catalytic Degradation of Organic Dyes Using Green Synthesized Fe3O4-Cellulose-Copper Nanocomposites,” Journal of Molecular Structure 1218 (2020): 128488.
  • (a) M.A. Khalilzadeh, S. Hosseini, A.S. Rad, and R.A. Venditti, Journal of Agricultural and Food Chemistry 68, no. 32 (2020): 8710–9. (b) S.K. Park, T. Ishikawa, and Y. Tokura, Physical Review B58 (1998): 3717. (c) T. Jiang, Y. Wang, D. Meng, and M. Yu, Superlattice Microst 85 (2015). (d) C. Liu, Journal of Alloys and Compounds 656, no. 24 (2016). (e) Y. Wu, and T. He, “Ag loading induced visible light photocatalytic activity for pervoskite SrTiO3 nanofibers,” Spectrochimica Acta Part A 199, no. 283 (2018).
  • A.B. Djurišić, X. Chen, Y.H. Leung, and A. Man, “ZnO Nanostructures: Growth, Properties and Applications,” Journal of Materials Chemistry 22, no. 14 (2012): 6526–35.
  • (a) B. Halliwell, “Antioxidant Defence Mechanisms: From the Beginning to the End (of the Beginning),” Free Radical Research 31, no. 4 (1999): 261–72. (b) F. Ahmadi, M. Kadivar, and M. Shahedi, Food Chemistry 105 (2007): 57–64.
  • Mark A. Babizhayev, Anatoly I. Deyev, Valentina N. Yermakova, Igor V. Brikman, and Johan Bours, “Lipid Peroxidation and Cataracts: N-Acetylcarnosine as a Therapeutic Tool to Manage Age-Related Cataracts in Human and in Canine Eyes,” Drugs in R&D 5, no. 3 (2004): 125–39.
  • L. Liu, and M. Meydani, “Combined Vitamin C and E Supplementation Retards Early Progression of Arteriosclerosis in Heart Transplant Patients,” Nutrition Reviews 60, no. 11 (2002): 368–71.
  • (a) E. Ezzatzadeh, and Z.S. Hossaini, “Green Synthesis and Antioxidant Activity of Novel Series of Benzofurans from Euparin Extracted of Petasites hybridus,” Natural Product Research 33, no. 11 (2019): 1617–23. (b) E. Ezzatzadeh, and Z.S. Hossaini, Natural Product Research 34 (2020): 923–29. (c) E. Ezzatzadeh, and Z.S. Hossaini, Molecular Diversity 24 (2019): 81–91. (d) E. Ezzatzadeh, “Green synthesis of α-aminophosphonates using ZnO nanoparticles as an efficient catalyst,” Zeitschrift Für Naturforschung B 73 (2018): 179–84.
  • (a) I. Yavari, M. Sabbaghan, and Z.S. Hossaini, “Efficient Synthesis of Functionalized 2,5-Dihydrofurans and 1,5-Dihydro-2H-Pyrrol-2-Ones by Reaction of Isocyanides with Activated Acetylenes in the Presence of Hexachloroacetone,” Monatshefte Für Chemie - Chemical Monthly 139, no. 6 (2008): 625–8. (b) I. Yavari, M. Sabbaghan, and Z.S. Hossaini, Synlett (2008): 1153–4. (c) I. Yavari, Z.S. Hossaini, M. Sabbaghan, and M. Ghazanfarpour-Darjani, Tetrahedron 63 (2007): 9423–8. (d) I. Yavari, M. Sabbaghan, Z.S. Hossaini, and M. Ghazanfarpour-Darjani, Helvetica Chimica Acta 91 (2008) 1144–7. (e) M. Rajabi, Z.S. Hossaini, M.A. Khalilzadeh, Sh Datta, M. Halder, and Sh A. Mousa, Journal of Photochemistry and Photobiology B: Biology 148 (2015): 66–72.
  • (a) Z.S. Hossaini, D. Zareyee, F. Sheikholeslami-Farahani, S. Vaseghi, and A. Zamani, Heteroatom Chemistry 28, no. 2 (2017): e21362–1942. (b) F. Rostami-Charati, Z.S. Hossaini, D. Zareyee, S. Afrashteh, and M. Hosseinzadeh, “ZnO-Nanorods as an Efficient Catalyst for the Synthesis of 1,3-Thiazolidine Derivatives by Aqueous Multicomponent Reactions of Isothiocyanates,” Journal of Heterocyclic Chemistry 54 (2017): 1937. (c) F. Rostami‐Charati, Z.S. Hossaini, M.A. Khalilzadeh, and H. Jafaryan, “Synthesis of Furanone Derivatives Using 15-Nonacosanole Extracted from Fumaria officinalis in the Presence of KF/Clinoptilolite Nanoparticles,” Journal of Heterocyclic Chemistry 49 (2012): 217–20. (d) F. Rostami-Charati, and Z.S. Hossaini, “Facile synthesis of phosphonates via catalyst-free multicomponent reactions in water,” Synlett 23 (2012): 2397–9.
  • (a) F. Rostami-Charati, Z.S. Hossaini, R. Rostamian, A. Zamani, and M. Abdoli, “Green Synthesis of Indol-2-One Derivatives from N-Alkylisatins in the Presence of KF/Clinoptilolite Nanoparticles,” Chemistry of Heterocyclic Compounds 53, no. 4 (2017): 480–3. (b) I. Yavari, S. Seyfi, Z.S. Hossaini, M. Sabbaghan, and F. Shirgahi-Talari, “Efficient synthesis of 2-thioxo-1, 3-thiazolanes from primary amines, CS2, and ethyl bromopyruvate,” Monatshefte Für Chemie-Chemical Monthly 139 (2008): 1479–82. (c) S. Rezayati, F. Sheikholeslami-Farahani, Z.S. Hossaini, R. Hajinasiri, and S. Afshari Sharif Abad, “Regioselctive thiocyanation of aromatic and heteroaromatic compounds using a novel bronsted acidic ionic liquid,” Combinatorial Chemistry and High Throughput Screening 9 (2016): 720–7. (d) F. Tavakolinia, T. Baghipour, Z.S. Hossaini, D. Zareyee, and M.A. Khalilzadeh, “Antiproliferative activity of novel thiopyran analogs on MCF-7 breast and HCT-15 colon cancer cells: synthesis, cytotoxicity, cell cycle analysis, and DNA-binding,” Nucleic Acid Therapeutics 22 (2012): 265–270.
  • (a) F. Rostami-Charati, Z.S. Hossaini, F. Sheikholeslami-Farahani, Z. Azizi, and S.A. Siadati, “Synthesis of 9H-Furo [2,3-f]Chromene Derivatives by Promoting ZnO Nanoparticles,” Combinatorial Chemistry & High Throughput Screening 18, no. 9 (2015): 872–80. (b) H. Sajjadi-Ghotbabadi, Sh Javanshir, and F. Rostami-Charati, “Nano KF/Clinoptilolite: An Effective Heterogeneous Base Nanocatalyst for Synthesis of Substituted Quinolines in Water,” Catalysis Letters 146 (2016): 338–44. (c) I. Yavari, M. Ghazanfarpour-Darjani, Z.S. Hossaini, M. Sabbaghan, and N. Hosseini, “Methoxide ion promoted efficient synthesis of 1, 3-oxathiolane-2-thiones by reaction of oxiranes and carbon disulfide,” Synlett 06 (2008): 889–91. (d) I. Yavari, Z.S. Hossaini, S. Souri, and S. Seyfi, “Diastereoselective synthesis of fused [1, 3] thiazolo [1, 3] oxazins and [1, 3] oxazino [2, 3-b][1, 3] benzothiazoles,” Molecular Diversity 13 (2009): 439–43.
  • (a) R. Hajinasiri, Z.S. Hossaini, and F. Rostami‐Charati, “Efficient Synthesis of α-Aminophosphonates via One-Pot Reactions of Aldehydes, Amines, and Phosphates in Ionic Liquid,” Heteroatom Chemistry 22, no. 5 (2011): 625–9. (b) F. Rostami Charati, Z.S. Hossaini, and M.R. Hosseini-Tabatabaei, “A simple synthesis of oxaphospholes,” Phosphorus, Sulfur, and Silicon and the Related Elements 186 (2011): 1443–48. (c) Z.S. Hossaini, F. Sheikholeslami-Farahani, and F. Rostami-Charati, “Green synthesis of phosphoryl-2-oxo-2H-pyran via three component reaction of trialkyl phosphites,” Combinatorial Chemistry & High Throughput Screening 17 (2014): 804–807.
  • (a) I. Yavari, M. Nematpour, and Z.S. Hossaini, “Ph3P-Mediated One-Pot Synthesis of Functionalized 3,4-Dihydro-2H-1,3-Thiazines from N,N′-Dialkylthioureas and Activated Acetylenes in Water,” Monatshefte Für Chemie - Chemical Monthly 141, no. 2 (2010): 229–32. (b) S. Rezayati, R. Hajinasiri, Z.S. Hossaini, S. Abbaspour, “Chemoselective synthesis of 1,1-diacetates (acylals) using 1,1'‐butylenebispyridinium hydrogen sulfate as a new, halogen‐free and environmental-friendly catalyst under solvent-free conditions,” Asian Journal of Green Chemistry 2 (2018): 268–80. (c) F. Sheikholeslami-Farahani, Z.S. Hossaini, and F. Rostami-Charati, “Solvent-free synthesis of substituted thiopyrans via multicomponent reactions of α-haloketones,” Chinese Chemical Letters, 25 (2014): 152–4.
  • (a) I. Yavari, and Z.S. Hossaini, “Synthesis of Fused α-Methylene-γ-Butyrolactone Derivatives through Pyridine-Induced Addition of Phenols to Dimethyl Acetylenedicarboxylate,” Tetrahedron Letters 47, no. 26 (2006): 4465–8. (b) F. Rostami-Charati, Z.S. Hossaini, R. Rostamian, M. Ghambarian, and A. Zamani, Green synthesis of indol-2-one derivatives from N-alkylisatins in the presence of KF/clinoptilolite nanoparticles. Chemistry of Heterocyclic Compounds 53 (2017): 480–3. (c) Z.S. Hossaini, D. Zareyee, F. Sheikholeslami‐Farahani, S. Vaseghi, and A. Zamani, “ZnO‐NR as the efficient catalyst for the synthesis of new thiazole and cyclopentadienone phosphonate derivatives in water,” Heteroatom Chemistry. 28 (2017): e21362. (d) F. Salehi Borban, S. Gharachorloo, and F. Zamani Hargalani, “Check Amount of heavy metals in muscle and fish oil Rutilus frisii kutum, Clupeonella cultriventris and Liza saliens,” Journal of Food Technology and Nutrition 6 (2017): 75–104. (e) M. Rezaei Nazari, V. Abdossi, F. Zamani Hargalani, and K. Larijani, Research Square https://doi.org/10.21203/rs.3.rs-708123/v1.
  • (a) Z.S. Hossaini, F. Sheikholeslami-Farahani, and F. Rostami-Charati, “Green Synthesis of Phosphoryl-2-Oxo-2H-Pyran via Three Component Reaction of Trialkyl Phosphites,” Combinatorial Chemistry & High Throughput Screening 17, no. 9 (2014): 804–7. (b) I. Yavari, and Z.S. Hossaini, Tetrahedron Letters 47 (2006): 4465–8. (c) Yavari, I. Seyfi, S. Nematpour, M. Hossaini, and Z.S. Helvetica Chimica Acta 93 (2010): 1413–7.
  • S.P. Rajendran, and K. Sengodan, “Synthesis and Characterization of Zinc Oxide and Iron Oxide Nanoparticles Using Sesbania Grandiflora Leaf Extract as Reducing Agent,” Journal of Nanoscience 2017 (2017): 1–7.
  • K. Shimada, K. Fujikawa, K. Yahara, and T. Nakamura, “Antioxidative Properties of Xanthan on the Autoxidation of Soybean Oil in Cyclodextrin Emulsion,” Journal of Agricultural and Food Chemistry 40, no. 6 (1992): 945–8.
  • G.C. Yen, and P.D. Duh, “Scavenging Effect of Methanolic Extracts of Peanut Hulls on Free-Radical and Active-Oxygen Species,” Journal of Agricultural and Food Chemistry 42, no. 3 (1994): 629–32.
  • A. Yildirim, A. Mavi, and A.A. Kara, “Determination of Antioxidant and Antimicrobial Activities of Rumex Crispus L. Extracts,” Journal of Agricultural and Food Chemistry 49, no. 8 (2001): 4083–9.
  • A.M. Bidchol, A. Wilfred, P. Abhijna, and R. Harish, “Free Radical Scavenging Activity of Aqueous and Ethanolic Extract of Brassica oleracea L. var. italica,” Food and Bioprocess Technology 4, no. 7 (2011): 1137–43.

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