Green synthesis of 2-amino-3-cyanopyridines via a cooperative vinylogous anomeric-based oxidation and their antiproliferative effects on liver, breast, and prostate cancer studies

References

• Siegel, R. L.; Miller, K. D.; Jemal, A. Cancer Statistics, 2020. CA. A Cancer J. Clin. 2020, 70, 7–30. DOI: 10.3322/caac.21590.
   PubMed Web of Science ®Google Scholar
• Zhang, F.; Zhao, Y.; Sun, L.; Ding, L.; Gu, Y.; Gong, P. Synthesis and Anti-Tumor Activity of 2-Amino-3-Cyano-6-(1H-Indol-3-yl)-4-Phenylpyridine Derivatives In Vitro. Eur. J. Med. Chem. 2011, 46, 3149–3157. DOI: 10.1016/j.ejmech.2011.03.055.
   PubMed Web of Science ®Google Scholar
• Deng, J.; Sanchez, T.; Al-Mawsawi, L. Q.; Dayam, R.; Yunes, R. A.; Garofalo, A.; Bolger, M. B.; Neamati, N. Discovery of Structurally Diverse HIV-1 Integrase Inhibitors Based on a Chalcone Pharmacophore. Bioorganic Med. Chem. 2007, 15, 4985–5002. DOI: 10.1016/j.bmc.2007.04.041.
   PubMed Web of Science ®Google Scholar
• Murata, T.; Shimada, M.; Sakakibara, S.; Yoshino, T.; Kadono, H.; Masuda, T.; Shimazaki, M.; Shintani, T.; Fuchikami, K.; Sakai, K.; et al. Discovery of Novel and Selective IKK-β Serine-Threonine Protein Kinase Inhibitors. Part 1. Bioorganic Med. Chem. Lett. 2003, 13, 913–918. DOI: 10.1016/S0960-894X(02)01046-6.
   PubMed Web of Science ®Google Scholar
• Mantri, M.; De Graaf, O.; Van Veldhoven, J.; Göblyös, A.; Von Frijtag Drabbe Künzel, J. K.; Mulder-Krieger, T.; Link, R.; De Vries, H.; Beukers, M. W.; Brussee, J.; et al. 2-Amino-6-Furan-2-Yl-4-Substituted Nicotinonitriles as A2a Adenosine Receptor Antagonists. J. Med. Chem. 2008, 51, 4449–4455. DOI: 10.1021/jm701594y.
   PubMed Web of Science ®Google Scholar
• Tang, J.; Wang, L.; Yao, Y.; Zhang, L.; Wang, W. One-Pot Synthesis of 2-Amino-3-Cyanopyridine Derivatives Catalyzed by Ytterbium Perfluorooctanoate [Yb(PFO)3]. Tetrahedron Lett. 2011, 52, 509–511. DOI: 10.1016/j.tetlet.2010.11.102.
   Web of Science ®Google Scholar
• Behrouz, S. Highly Efficient Four-Component Synthesis of 2-Amino-3-Cyanopyridines Using Doped Nano-Sized Copper (I) Oxide (Cu 2 O) on Melamine – Formaldehyde Resin. J. Chem. Res. 2016, 40, 540–544.DOI: 10.3184/174751916X14709292404728.
   Google Scholar
• Zolfigol, M. A.; Kiafar, M.; Yarie, M.; Taherpour, A.; Fellowes, T.; Nicole Hancok, A.; Yari, A. A Convenient Method for Preparation of 2-Amino-4,6-Diphenylnicotinonitrile Using HBF4 as an Efficient Catalyst via an Anomeric Based Oxidation: A Joint Experimental and Theoretical Study. J. Mol. Struct. 2017, 1137, 674–680. DOI: 10.1016/j.molstruc.2017.02.083.
   Web of Science ®Google Scholar
• Zolfigol, M. A.; Yarie, M. Fe3O4@TiO2@O2PO2(CH2)NHSO3H as a Novel Nanomagnetic Catalyst: Application to the Preparation of 2-Amino-4,6-Diphenylnicotinonitriles via Anomeric-Based Oxidation. Appl. Organomet. Chem. 2017, 31, 1–10. DOI: 10.1002/aoc.3598.
   Web of Science ®Google Scholar
• Mansoor, S. S.; Aswin, K.; Logaiya, K.; Sudhan, P. N.; Malik, S. Aqueous Media Preparation of 2-Amino-4,6-Diphenylnicotinonitriles Using Cellulose Sulfuric Acid as an Efficient Catalyst. Res. Chem. Intermed. 2014, 40, 871–885. DOI: 10.1007/s11164-012-1008-9.
   Web of Science ®Google Scholar
• Sun, J.; Gong, S. S.; Sun, Q. A Novel Strategy for the Synthesis of Azetidine. Amr. 2013, 830, 135–138. DOI: 10.4028/www.scientific.net/AMR.830.135.
   Google Scholar
• Kheilkordi, Z.; Mohammadi Ziarani, G.; Bahar, S.; Badiei, A. The Green Synthesis of 2-Amino-3-Cyanopyridines Using SrFe12O19 Magnetic Nanoparticles as Efficient Catalyst and Their Application in Complexation with Hg2+ Ions. J. Iran. Chem. Soc. 2019, 16, 365–372. DOI: 10.1007/s13738-018-1514-9.
   Web of Science ®Google Scholar
• Khalifeh, R.; Ghamari, M. A Multicomponent Synthesis of 2-Amino-3-Cyanopyridine Derivatives Catalyzed by Heterogeneous and Recyclable Copper Nanoparticles on Charcoal. J. Braz. Chem. Soc. 2016, 27, 759–768. DOI: 10.5935/0103-5053.20150327.
   Web of Science ®Google Scholar
• Yahyazadeh, A.; Abbaspour-Gilandeh, E.; Aghaei-Hashjin, M. Four-Component Synthesis of 2-Amino-3-Cyanopyridine Derivatives Catalyzed by Cu@imineZCMNPs as a Novel, Efficient and Simple Nanocatalyst under Solvent-Free Conditions. Catal. Lett. 2018, 148, 1254–1262. DOI: 10.1007/s10562-018-2318-3.
   Web of Science ®Google Scholar
• Zolfigol, M. A.; Kiafar, M.; Yarie, M.; Taherpour, A.; Saeidi-Rad, M. Experimental and Theoretical Studies of the Nanostructured {Fe3O4@SiO2@(CH2)3Im}C(CN)3 Catalyst for 2-Amino-3-Cyanopyridine Preparation: Via an Anomeric Based Oxidation. RSC Adv. 2016, 6, 50100–50111. DOI: 10.1039/C6RA12299J.
   Web of Science ®Google Scholar
• Kalhor, S.; Yarie, M.; Rezaeivala, M.; Zolfigol, M. A. Novel Magnetic Nanoparticles with Morpholine Tags as Multirole Catalyst for Synthesis of Hexahydroquinolines and 2-Amino-4,6-Diphenylnicotinonitriles through Vinylogous Anomeric-Based Oxidation. Res. Chem. Intermed. 2019, 45, 3453–3480. DOI: 10.1007/s11164-019-03802-7.
   Web of Science ®Google Scholar
• Karimi, H. A Novel Preparation of Zirconium Phosphate Nanoparticle and Its Application in Multi-Component Reactions. Iran. J. Chem. Chem. Eng. 2017, 36, 11–19.
   Google Scholar
• Swamy, K.; Pagilla, S. Synthesis of Pyridine Derivatives in Multicomponent Cascade Coupling Strategy Using Green Solvent. JCCS. 2017, 7, 1147–1152. DOI: 10.29055/jccs/522.
   Google Scholar
• Balaswamy, P.; Aravind, S.; Satyanarayana, B. Polyethylene Glycol-400 Used as Phase Transfer Catalyst for One-Pot Synthesis of 2-Amino-3-Cyanopyridine Derivatives under Aqueous Conditions. RJC. 2017, 10, 1334–1339. DOI: 10.7324/RJC.2017.1041903.
   Google Scholar
• Khaksar, S.; Yaghoobi, M. A Concise and Versatile Synthesis of 2-Amino-3-Cyanopyridine Derivatives in 2,2,2-Trifluoroethanol. J. Fluor. Chem. 2012, 142, 41–44. DOI: 10.1016/j.jfluchem.2012.06.009.
   Web of Science ®Google Scholar
• Tamaddon, F.; Azadi, D. Nicotinium Methane Sulfonate (NMS): A Bio-Renewable Protic Ionic Liquid and Bi-Functional Catalyst for Synthesis of 2-Amino-3-Cyano Pyridines. J. Mol. Liq. 2018, 249, 789–794. DOI: 10.1016/j.molliq.2017.10.153.
   Web of Science ®Google Scholar
• Erşatır, M.; Yıldırım, M.; Giray, E. S.; Yalın, S. Synthesis and Antiproliferative Evaluation of Novel Biheterocycles Based on Coumarin and 2-Aminoselenophene-3-Carbonitrile Unit. Monatsh. Chem. 2020, 151, 625–636. DOI: 10.1007/s00706-020-02573-x.
   Web of Science ®Google Scholar
• Erşatır, M.; Yıldırım, M.; Giray, E. S. Carbostyril Derivatives: Synthesis of Novel Carbostyril-3′-Carbonitrilselenophene Hybrid Compounds and Investigation of Their Antiproliferative Properties on Prostate and Breast Cancer. Synth. Commun. 2020, 0, 1–12. DOI: 10.1080/00397911.2020.1825744.
   Web of Science ®Google Scholar
• Khaksar, S.; Yaghoobi, M.; Zolfigol, M. A.; Kiafar, M.; Yarie, M.; Taherpour, A.; Fellowes, T.; Nicole Hancok, A.; Yari, A.; Tang, J.; et al. Synthesis of 2-Amino-4,6-Diarylnicotinonitrile in the Presence of CoFe2O4@SiO2-SO3H as a Reusable Solid Acid Nanocatalyst under Microwave Irradiation in Solvent-Freeconditions. Res. Chem. Intermed. 2017, 40, 2169–2176. DOI: 10.1007/s13738-018-1514-9..
   Web of Science ®Google Scholar
• Yarie, M. Catalytic Vinylogous Anomeric Based Oxidation (Part I). Iran. J. Catal. 2019, 10, 79–83.
   Google Scholar
• Yarie, M. Catalytic Anomeric Based Oxidation. Iran. J. Catal. 2017, 7, 29–37.
   Web of Science ®Google Scholar
• Babaee, S.; Zarei, M.; Sepehrmansourie, H.; Zolfigol, M. A.; Rostamnia, S. Synthesis of Metal-Organic Frameworks MIL-101(Cr)-NH2 Containing Phosphorous Acid Functional Groups: Application for the Synthesis of N-Amino-2-pyridone and Pyrano [2,3-c]pyrazole Derivatives via a Cooperative Vinylogous Anomeric-Based Oxidation. ACS Omega. 2020, 5, 6240–6249. DOI: 10.1021/acsomega.9b02133.
   PubMed Web of Science ®Google Scholar
• Ghasemi, P.; Yarie, M.; Zolfigol, M. A.; Taherpour, A. A.; Torabi, M. Ionically Tagged Magnetic Nanoparticles with Urea Linkers: Application for Preparation of 2-Aryl-Quinoline-4-Carboxylic Acids via an Anomeric-Based Oxidation Mechanism. ACS Omega. 2020, 5, 3207–3217. DOI: 10.1021/acsomega.9b03277.
   PubMed Web of Science ®Google Scholar
• Safari, J.; Banitaba, S. H.; Khalili, S. D. Ultrasound-Promoted an Efficient Method for One-Pot Synthesis of 2-Amino-4,6-Diphenylnicotinonitriles in Water: A Rapid Procedure without Catalyst. Ultrason. Sonochem. 2012, 19, 1061–1069. DOI: 10.1016/j.ultsonch.2012.01.005.
   PubMed Web of Science ®Google Scholar