ZnO nanoparticles catalyzed synthesis of bis- and poly(imidazoles) as potential anticancer agents

References

• Steinman, R. A.; Brufsky, A. M.; Oesterreich, S. Zoledronic Acid Effectiveness against Breast Cancer Metastases – A Role for Estrogen in the Microenvironment? Breast Cancer Res. 2012, 14, 213–221. doi:10.1186/bcr3223.
   PubMed Web of Science ®Google Scholar
• Mishra, R.; Ganguly, S. Imidazole as an Anti-Epileptic: An Overview. Med. Chem. Res. 2012, 21, 3929–3939. doi:10.1007/s00044-012-9972-6.
   Web of Science ®Google Scholar
• Burnier, M.; Wuerzner, G. Pharmacokinetic Evaluation of Losartan. Expert Opin. Drug Metab. Toxicol. 2011, 7, 643–649. doi:10.1517/17425255.2011.570333.
   PubMed Web of Science ®Google Scholar
• Oncology, T. L. Cancer in Developing Countries: Can the Revolution Begin? Lancet. Oncol. 2011, 12, 201. doi:10.1016/S1470-2045(11)70046-8.
   PubMed Web of Science ®Google Scholar
• Ali, I.; Lone, M. N.; Aboul-Enein, H. Y. Imidazoles as Potential Anticancer Agents. Medchemcomm 2017, 8, 1742–1773. doi:10.1039/C7MD00067G.
   PubMed Web of Science ®Google Scholar
• Kulkarni, A.; Török, B. Microwave-Assisted Multicomponent Domino Cyclization–Aromatization: An Efficient Approach for the Synthesis of Substituted Quinolines. Green Chem. 2010, 12, 875. doi:10.1039/c001076f.
   Web of Science ®Google Scholar
• Cioc, R. C.; Ruijter, E.; Orru, R. V. A. Multicomponent Reactions: Advanced Tools for Sustainable Organic Synthesis. Green Chem. 2014, 16, 2958–2975. doi:10.1039/C4GC00013G.
   Web of Science ®Google Scholar
• Abd El-Fatah, N. A.; Darweesh, A. F.; Mohamed, A. A.; Abdelhamid, I. A.; Elwahy, A. H. M. Experimental and Theoretical Study on the Regioselective Bis- and Polyalkylation of 2-Mercaptonicotinonitrile and 2-Mercaptopyrimidine-5-Carbonitrile Derivatives. Tetrahedron 2017, 73, 1436–1450. doi:10.1016/j.tet.2017.01.047.
   Web of Science ®Google Scholar
• Elwahy, A. H. M.; Shaaban, M. R. Synthesis of Heterocycles and Fused Heterocycles Catalyzed by Nanomaterials. RSC Adv. 2015, 5, 75659–75710. doi:10.1039/C5RA11421G.
   Web of Science ®Google Scholar
• Banerjee, S.; Saha, A. Free-ZnO Nanoparticles: A Mild, Efficient and Reusable Catalyst for the One-Pot Multicomponent Synthesis of Tetrahydrobenzo[b]Pyran and Dihydropyrimidone Derivatives. New J. Chem. 2013, 37, 4170–4175. doi:10.1039/c3nj00723e.
   Web of Science ®Google Scholar
• Rao, G.; Kaushik, M.; Halve, A. An Efficient Synthesis of Naphtha [1, 2-E] Oxazinone and 14-Substituted-14H-Dibenzo [A, J] Xanthene Derivatives Promoted by Zinc Oxide Nanoparticle under Thermal and Solvent-Free Conditions. Tetrahedron Lett. 2012, 53, 2741–2744. doi:10.1016/j.tetlet.2012.03.085.
   Web of Science ®Google Scholar
• Dallinger, D.; Kappe, C. O. Microwave-Assisted Synthesis in Water as Solvent. Chem. Rev. 2007, 107, 2563–2591. doi:10.1021/cr0509410.
   PubMed Web of Science ®Google Scholar
• Gawande, M. B.; Shelke, S. N.; Zboril, R.; Varma, R. S. Microwave-Assisted Chemistry: Synthetic Applications for Rapid Assembly of Nanomaterials and Organics. Acc. Chem. Res. 2014, 47, 1338–1348. doi:10.1021/ar400309b.
   PubMed Web of Science ®Google Scholar
• Abdelmoniem, A. M.; Elwahy, A. H. M.; Abdelhamid, I. A. Bis (Indoline-2,3-Diones): Versatile Precursors for Novel Bis (2’,6’-Dicarbonitrile) Derivatives. Arkivoc 2016, 2016 (iii), 304–312.
   Google Scholar
• Salem, M. E.; Darweesh, A. F.; Farag, A. M.; Elwahy, A. H. M. Synthesis and Structures of Novel Multi-Armed Molecules Involving Benzene as a Core and 4-Phenylthiazole, 4-Pyrazolylthiazole, or Thiadiazole Units as Arms. J. Heterocyclic Chem. 2017, 54, 586–595. doi:10.1002/jhet.2629.
   Web of Science ®Google Scholar
• Salem, M. E.; Darweesh, A. F.; Mekky, A. E. M.; Farag, A. M.; Elwahy, A. H. M. 2-Bromo-1-(1H-Pyrazol-4-Yl)Ethanone: Versatile Precursor for Novel Mono- and Bis[Pyrazolylthiazoles]. J. Heterocyclic Chem. 2017, 54, 226–234. doi:10.1002/jhet.2571.
   Web of Science ®Google Scholar
• Salama, S. K.; Darweesh, A. F.; Abdelhamid, I. A.; Elwahy, A. H. M. Microwave Assisted Green Multicomponent Synthesis of Novel Bis(2-Amino-Tetrahydro-4H-Chromene-3-Carbonitrile) Derivatives Using Chitosan as Eco-Friendly Basic Catalyst. J. Heterocyclic Chem. 2017, 54, 305–312. doi:10.1002/jhet.2584.
   Web of Science ®Google Scholar
• Dolle, R. E. Comprehensive Survey of Combinatorial Library Synthesis: 2004. J. Comb. Chem. 2005, 7, 739–798. doi:10.1021/cc050082t.
   PubMed Web of Science ®Google Scholar
• Dolle, R. E. Comprehensive Survey of Combinatorial Library Synthesis: 2003. J. Comb. Chem. 2004, 6, 623–679. doi:10.1021/cc0499082.
   PubMedGoogle Scholar
• Menger, F. M. Chemistry of Multi-Armed Organic Compounds. In Biomimetic and Bioorganic Chemistry III; Vögtle, F.; Weber, E., Eds.; Springer: Berlin, Heidelberg, 1986; pp 1–15. doi:10.1007/3-540-16724-2_5.
   Google Scholar
• Hadjichristidis, N.; Pitsikalis, M.; Iatrou, H.; Driva, P.; Sakellariou, G.; Chatzichristidi, M. Polymers with Star-Related Structures. In Polymer Science: A Comprehensive Reference; Moeller, M.; Matyjaszewski, K., Eds.; Elsevier: Amsterdam, 2012; pp 29–111. doi:10.1016/B978-0-444-53349-4.00161-8.
   Google Scholar
• Muraoka, H.; Mori, M.; Ogawa, S. A Comparative Study of the Electronic Property of a Series of 2,4,6-Tri(5-Aryl-2-Thienyl)-1,3,5-Triazines Controlled by the Electronic Nature of Aryl Groups. Phosphorus, Sulfur Silicon Relat. Elem. 2015, 190, 1382–1391. doi:10.1080/10426507.2015.1043047.
   Web of Science ®Google Scholar
• Calió, L.; Kazim, S.; Grätzel, M.; Ahmad, S. Hole-Transport Materials for Perovskite Solar Cells. Angew. Chem. Int. Ed. 2016, 55, 14522–14545. doi:10.1002/anie.201601757.
   PubMed Web of Science ®Google Scholar
• Zhang, W.; Jin, Y. Dynamic Covalent Chemistry: Principles, Reactions, and Applications; John Wiley & Sons, New York City, NY, 2017. doi:10.1002/9781119075738.
   Google Scholar
• Pathak, S. K.; Nath, S.; De, J.; Pal, S. K.; Achalkumar, A. S. Contrasting Effects of Heterocycle Substitution and Branched Tails in the Arms of Star-Shaped Molecules. New J. Chem. 2017, 41, 4680–4688. doi:10.1039/C7NJ00911A.
   Web of Science ®Google Scholar
• Astruc, D.; Boisselier, E.; Ornelas, C. Dendrimers Designed for Functions: From Physical, Photophysical, and Supramolecular Properties to Applications in Sensing, Catalysis, Molecular Electronics, Photonics, and Nanomedicine. Chem. Rev. 2010, 110, 1857–1959. doi:10.1021/cr900327d.
   PubMed Web of Science ®Google Scholar
• Grillaud, M.; Bianco, A. Multifunctional Adamantane Derivatives as New Scaffolds for the Multipresentation of Bioactive Peptides. J. Pept. Sci. 2015, 21, 330–345. doi:10.1002/psc.2719.
   PubMed Web of Science ®Google Scholar
• Abdella, A. M.; Moatasim, Y.; Ali, M. A.; Elwahy, A. H. M.; Abdelhamid, I. A. Synthesis and Anti-Influenza Virus Activity of Novel Bis(4H-Chromene-3-Carbonitrile) Derivatives. J. Heterocyclic Chem. 2017, 54, 1854–1862. doi:10.1002/jhet.2776.
   Web of Science ®Google Scholar
• Al-Awadi, N. A.; Ibrahim, M. R.; Abdelhamid, I. A.; Elnagdi, M. H. Arylhydrazonals as the Aldehyde Component in Baylis-Hillman Reactions. Tetrahedron 2008, 64, 8202–8205. doi:10.1016/j.tet.2008.06.026.
   Web of Science ®Google Scholar
• Elwahy, A. H. M.; Abdelhamid, A. I.; Sanad, S.M. H.; Kassab, R. M. Microwave Assisted Multi-Component Synthesis of Novel Bis(1,4-Dihydropyridines) Based Arenes or Heteroarenes. Heterocycles 2016, 92, 910. doi:10.3987/COM-16-13441.
   Web of Science ®Google Scholar
• Elwahy, A. H. M.; Shaaban, M. R. Synthesis of Furo-, Pyrrolo-, and Thieno-Fused Heterocycles by Multi-Component Reactions (Part 1). Curr. Org. Synth. 2015, 10, 425–466. doi:10.2174/1570179411310030007.
   Web of Science ®Google Scholar
• Shaaban, M. R.; Elwahy, A. H. M. Synthesis of Oxazolo-, Thiazolo-, Pyrazolo-, and Imidazo-Fused Heterocycles by Multi-Component Reactions (Part 2). Cos 2014, 11, 471–525. doi:10.2174/15701794113106660076.
   Web of Science ®Google Scholar
• Abdella, A. M.; Elwahy, A. H. M.; Abdelhamid, I. A. Multicomponent Synthesis of Novel Bis(2-Amino-Tetrahydro-4H-Chromene-3-Carbonitrile) Derivatives Linked to Arene or Heteroarene Cores. Curr. Org. Synth. 2016, 13, 601–610.
   Web of Science ®Google Scholar
• Shaaban, M. R.; Elwahy, A. H. M. Bis(α-Bromo Ketones): Versatile Precursors for Novel Bis(S-Triazolo[3,4-B][1,3,4]Thiadiazines) and Bis(as-Triazino[3,4-B][1,3,4]Thiadiazines). J. Heterocyclic Chem. 2012, 49, 640–645. doi:10.1002/jhet.861.
   Web of Science ®Google Scholar
• Abdelmoniem, A. M.; Ghozlan, S. A. S.; Abdelmoniem, D. M.; Elwahy, A. H. M.; Abdelhamid, I. A. Facile One-Pot, Three-Component Synthesis of Novel Bis-Heterocycles Incorporating 5H-Chromeno[2,3-B]Pyridine-3-Carbonitrile Derivatives. J. Heterocyclic Chem. 2017, 54, 2844–2849. doi:10.1002/jhet.2890.
   Web of Science ®Google Scholar
• Elwahy, A. H. M.; Abbas, A. A. Bis(β-Difunctional) Compounds: Versatile Starting Materials for Novel Bis(Heterocycles). Synth. Commun. 2000, 30, 2903–2921. doi:10.1080/00397910008087441.
   Web of Science ®Google Scholar
• Sayed, O. M.; Mekky, A. E. M.; Farag, A. M.; Elwahy, A. H. M. 3,4-Bis(Bromomethyl)Thieno[2,3-B]Thiophene: Versatile Precursors for Novel Bis(Triazolothiadiazines), Bis(Quinoxalines), Bis(Dihydrooxadiazoles), and Bis(Dihydrothiadiazoles). J. Heterocyclic Chem. 2016, 53, 1113–1120. doi:10.1002/jhet.2373.
   Web of Science ®Google Scholar
• Salem, M. E.; Darweesh, A. F.; Farag, A. M.; Elwahy, A. H. M. 2-Bromo-1-(1H-Pyrazol-4-Yl)Ethanone: Versatile Precursors for Novel Mono-, Bis- and Poly{6-(1H-Pyrazol-4-Yl)-[1,2,4]Triazolo[3,4-b][1,3,4]Thiadiazines}. Tetrahedron 2016, 72, 712–719. doi:10.1016/j.tet.2015.12.024.
   Web of Science ®Google Scholar
• Sayed, O. M.; Mekky, A. E. M.; Farag, A. M.; Elwahy, A. H. M. 3. 4-Dimethyl-2,5-Functionalized Thieno[2,3-B]Thiophenes: Versatile Precursors for Novel Bis-Thiazoles. J. Sulfur Chem. 2015, 36, 124–134. doi:10.1080/17415993.2014.975131.
   Web of Science ®Google Scholar
• Elwahy, A. H. M.; Shaaban, M. R. Synthesis of Pyrido- and Pyrimido-Fused Heterocycles by Multi-Component Reactions (Part 3). Cos 2014, 11, 835–873. doi:10.2174/157017941106141023114039.
   Web of Science ®Google Scholar
• Hebishy, A. M. S.; Abdelhamid, I. A.; Elwahy, A. H. M. Synthesis of Novel Bis(Nicotinecarbonitrile) Derivatives. Arkivoc 2018, 2018, 97–108. doi:10.24820/ark.5550190.p010.367.
   Web of Science ®Google Scholar
• Hebishy, A. M. S.; Abdelhamid, I. A.; Elwahy, A. H. M. Synthesis of Novel Bis(Dihydropyridine) and Terpyridine Derivatives. Arkivoc 2018, 2018, 109–123. doi:10.24820/ark.5550190.p010.498.
   Web of Science ®Google Scholar
• Hebishy, A. M. S.; Elgemeie, G. H.; Elwahy, A. H. M. Novel Bis(2‐Cyanoketene‐S,S‐/S,N‐Acetals): Versatile Precursors for Novel Bis(Aminopyrazole) Derivatives. J. Heterocycl. Chem. 2019, 56, 1581–1587. doi:10.1002/jhet.3536.
   Web of Science ®Google Scholar
• Elwahy, A. H. M. A New Approach for the Design of Novel Hexa-Host Molecules. Tetrahedron Lett. 2001, 42, 5123–5126. doi:10.1016/S0040-4039.
   Web of Science ®Google Scholar
• Abdelhamid, I. A.; Darweesh, A. F.; Elwahy, A. H. M. Synthesis and Characterization of Poly(2,6-Dimethyl-4-Phenyl-1,4-Dihydropyridinyl)Arenes as Novel Multi-Armed Molecules. Tetrahedron Lett. 2015, 56, 7085–7088. doi:10.1016/j.tetlet.2015.11.015.
   Web of Science ®Google Scholar
• Elwahy, A. H. M.; Sarhan, R. M.; Badawy, M. A. Synthesis and Characterization of Poly([1,2,4]Triazolyl- and [1,2,4]Triazolo[3,4- b][1,3,4]Thiadiazinylsulfanylmethyl)Arenes: Novel Multi-Armed Molecules. Cos 2013, 10, 786–790. doi:10.2174/1570179411310050008.
   Web of Science ®Google Scholar
• Mohamed, M. F.; Darweesh, A. F.; Elwahy, A. H. M.; Abdelhamid, I. A. Synthesis, Characterization and Antitumor Activity of Novel Tetrapodal 1,4-Dihydropyridines: p53 Induction, Cell Cycle Arrest and Low Damage Effect on Normal Cells Induced by Genotoxic Factor H2O2. RSC Adv. 2016, 6, 40900–40910. doi:10.1039/C6RA04974E.
   Web of Science ®Google Scholar
• Chauveau, E.; Marestin, C.; Schiets, F.; Mercier, R. Synthesis of 2,4,5-Triarylimidazoles in Aqueous Solution, under Microwave Irradiation. Green Chem. 2010, 12, 1018. doi:10.1039/b925177d.
   Web of Science ®Google Scholar
• Kidwai, M.; Mothsra, P.; Bansal, V.; Somvanshi, R. K.; Ethayathulla, A. S.; Dey, S.; Singh, T. P. One-Pot Synthesis of Highly Substituted Imidazoles Using Molecular Iodine: A Versatile Catalyst. J. Mol. Catal. A Chem. 2007, 265, 177–182. doi:10.1016/j.molcata.2006.10.009.
   Web of Science ®Google Scholar
• Goli-Jolodar, O.; Shirini, F. Succinimidinium Hydrogensulfate ([H-Suc]HSO4) as a New, Green and Efficient Ionic Liquid Catalyst for the Synthesis of Tetrahydrobenzimidazo[2,1-B]Quinazolin-1(2H)-One, 1-(Benzothiazolylamino)Phenylmethyl-2-Naphthol, 1, 8-Dioxo-Octahydroxanthene and Bis(indolyl)methane derivatives. J. Iran. Chem. Soc. 2016, 13, 1077–1092. doi:10.1007/s13738-016-0822-1.
   Web of Science ®Google Scholar
• Puligoundla, R. G.; Karnakanti, S.; Bantu, R.; Nagaiah, K.; Kondra, S. B.; Nagarapu, L. A Simple, Convenient One-Pot Synthesis of [1,2,4]Triazolo/Benzimidazolo Quinazolinone Derivatives by Using Molecular Iodine. Tetrahedron Lett. 2013, 54, 2480–2483. doi:10.1016/j.tetlet.2013.02.099.
   Web of Science ®Google Scholar
• Wolkenberg, S. E.; Wisnoski, D. D.; Leister, W. H.; Wang, Y.; Zhijian Zhao, A.; Lindsley, C. W. Efficient Synthesis of Imidazoles from Aldehydes and 1,2-Diketones Using Microwave Irradiation. Org. Lett. 2004, 6, 1453–1456. doi:10.1021/ol049682b.
   PubMed Web of Science ®Google Scholar
• Safari, J.; Gandomi-Ravandi, S.; Akbari, Z. Sonochemical Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles Using Nanocrystalline MgAl2O4 as an Effective Catalyst. J. Adv. Res 2013, 4, 509–514. doi:10.1016/j.jare.2012.09.001.
   PubMedGoogle Scholar
• MaGee, D. I.; Bahramnejad, M.; Dabiri, M. Highly Efficient and Eco-Friendly Synthesis of 2-Alkyl and 2-Aryl-4,5-Diphenyl-1H-Imidazoles under Mild Conditions. Tetrahedron Lett. 2013, 54, 2591–2594. doi:10.1016/j.tetlet.2013.03.008.
   Google Scholar
• Xu, F.; Wang, N.; Tian, Y.; Li, G. Simple and Efficient Method for the Synthesis of Highly Substituted Imidazoles Catalyzed by Benzotriazole. J. Heterocyclic Chem. 2013, 50, 668–675. doi:10.1002/jhet.
   Web of Science ®Google Scholar
• Armstrong, L. G.; Lindoy, L. F. Nitrogen-oxygen Donor Macrocyclic Ligands. I. Nickel(II) Complexes of a New Series of Cyclic Ligands Derived from Salicylaldehydes. Inorg Chem. 1975, 14, 1322–1326. doi:10.1021/ic50148a024.
   Google Scholar
• Elwahy, A. H. M. Difunctional Heterocycles: A Convenient Synthesis of Bis(4,5-Dihydropyrazolyl) Ethers from Their Precursor Bis(Chalcones). J. Chem. Res. 1999, 1999, 602–603. doi:10.1039/a904716f.
   Google Scholar
• Muathen, H. A.; Aloweiny, N. A. M.; Elwahy, A. H. M. Synthesis of Novel Amide-Crownophanes and Schiff Base-Crownophanes Based on P-Phenylene, 2,6-Naphthalene, and 9,10-Anthracene. J. Heterocyclic Chem. 2009, 46, 656–663. doi:10.1002/jhet.129.
   Web of Science ®Google Scholar
• Ibrahim, Y. A.; Elwahy, A. H. M.; Elkareis, G. M. M. Synthesis of New Tetrabenzo Nitrogen-Oxygen Macrocycles Containing Two Amide Groups. J. Chem. Res 1994, 11, (S)414–415. (M)2321–2331. https://doi.org/0308-2342(1994):11<414:SONTNO>2.0.ZU;2-3. doi:10.1002/chin.199518195.
   Google Scholar
• Idris, M.; Coburn, C.; Fleetham, T.; Milam-Guerrero, J.; Djurovich, P. I.; Forrest, S. R.; Thompson, M. E. Phenanthro[9,10-D]Triazole and Imidazole Derivatives: High Triplet Energy Host Materials for Blue Phosphorescent Organic Light Emitting Devices. Mater. Horiz. 2019, 6, 1179–1186. doi:10.1039/C9MH00195F.
   Web of Science ®Google Scholar
• Baptista, P.; Roma-Rodrigues, C.; Fernandes, A.; Santos, S.; Martins, P.; Jesus, J.; Raposo, L. Heterocyclic Anticancer Compounds: Recent Advances and the Paradigm Shift towards the Use of Nanomedicine’s Tool Box. Molecules 2015, 20, 16852–16891. doi:10.3390/molecules200916852.
   PubMed Web of Science ®Google Scholar
• Murti, Y.; Mishra, P. Synthesis and Evaluation of Flavanones as Anticancer Agents. Indian J. Pharm. Sci. 2014, 76, 163–166.
   PubMed Web of Science ®Google Scholar
• Mosmann, T. Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays. J. Immunol. Methods 1983, 65, 55–63. (83)90303-4. doi:10.1016/0022-1759.
   PubMed Web of Science ®Google Scholar
• Elmallah, M. I. Y.; Micheau, O.; Eid, M. A. G.; Hebishy, A. M. S.; Abdelfattah, M. S. Marine Actinomycete Crude Extracts with Potent TRAIL-Resistance Overcoming Activity against Breast Cancer Cells. Oncol. Rep. 2017, 37, 3635–3642. doi:10.3892/or.2017.5595.
   PubMed Web of Science ®Google Scholar
• Perreault, M.; Maltais, R.; Roy, J.; Dutour, R.; Poirier, D. Design of a Mestranol 2-N-Piperazino-Substituted Derivative Showing Potent and Selective in Vitro and in Vivo Activities in MCF-7 Breast Cancer Models. ChemMedChem 2017, 12, 177–182. doi:10.1002/cmdc.201600482.
   PubMed Web of Science ®Google Scholar
• Awang, N.; Aziz, Z. A.; Farahana, K. N.; Meng, C. K. Cytotoxicity and Mode of Cell Death Induced by Triphenyltin (IV) Compounds in Vitro. Online J. Biol. Sci. 2014, 14, 84–93. doi:10.3844/OJBSSP.2014.84.93.
   Google Scholar