Synthesis, biological evaluation and computational studies of fused acridine containing 1,2,4-triazole derivatives as anticancer agents

References

• Gurova, K. New Hopes from Old Drugs: Revisiting DNA-Binding Small Molecules as Anticancer Agents. Future Oncol. 2009, 5, 1685. DOI: 10.2217/fon.09.127.
   PubMed Web of Science ®Google Scholar
• Kathiravan, M. K.; Khilare, M. M.; Nikoomanesh, K.; Chothe, A. S.; Jain, K. S. Topoisomerase as Target for Antibacterial and Anticancer Drug discovery. J. Enzyme Inhib. Med. Chem. 2013, 28, 419. DOI: 10.3109/14756366.2012.658785.
   PubMed Web of Science ®Google Scholar
• Wainwright, M. Acridine-a Neglected Antibacterial chromophore. J. Antimicrob. Chemother. 2001, 47, 1. DOI: 10.1093/jac/47.1.1.
   PubMed Web of Science ®Google Scholar
• Sugaya, T.; Mimura, Y.; Shida, Y.; Osawa, Y.; Matsukuma, I.; Ikeda, S.; Akinaga, S.; Morimoto, M.; Ashizawa, T.; Okabe, M . 6H-Pyrazolo[4,5,1-de]acridin-6-ones as a Novel Class of Antitumor Agents. Synthesis and Biological Activity. J. Med. Chem. 1994, 37, 1028. DOI: 10.1021/jm00033a020.
   PubMed Web of Science ®Google Scholar
• Kimura, M.; Okabayash, i. I.; Kato, A. Acridine Derivatives. V. Synthesis and P388 Antitumor Activity of the Novel 9-Anilino-2,3-Ethylenedioxyacridines. J. Heterocycl. Chem. 1993, 30, 1101. DOI: 10.1002/jhet.5570300446.
   Web of Science ®Google Scholar
• Zhang, B.; Li, X.; Li, B.; Gao, C. M.; Jiang, Y. Y. Acridine and Its Derivatives: A Patent Review (2009–2013)). Expert Opin. Ther. Pat. 2014, 24, 647. DOI: 10.1517/13543776.2014.902052.
   PubMed Web of Science ®Google Scholar
• Gensicka-Kowalewska, M.; Cholewiński, G.; Dzierzbicka, K. Recent Developments in the Synthesis and Biological Activity of Acridine/Acridone Analogues. RSC Adv. 2017, 7, 15776. DOI: 10.1039/C7RA01026E.
   Web of Science ®Google Scholar
• Gaĭdukevich, A. N.; Bashura, G. S.; Pertsev, I. M.; Piminov, A. F.; Piatikop, A. I. Determination of the Antimicrobial Activity of Some Acridine derivatives. Farm. Zh. 1973, 28, 50.
   PubMedGoogle Scholar
• Srivastava, A.; Pathak, R.; Bahel, S. Synthesis of antifungal N-acridin-5-yl, N′-α-aryloxy-butanoylhydrazines. J. Indian Chem. Soc. 1985, 62, 486
   Web of Science ®Google Scholar
• Srivastava, A.; Pathak, R. B.; Bahel, S. C. J. Indian Chem. Soc. 1985, 62, 486.
   Web of Science ®Google Scholar
• Ngadi, L.; Bsiri, N. G.; Mahamoud, A.; Galy, A. M.; Galy, J. P.; Soyfer, J. C.; Barbe, J.; Placidi, M.; Rodriguez-Santiago, J. I.; Mesa-Valle, C. Synthesis and Antiparasitic Activity of New 1-nitro, 1-amino and 1-acetamido 9-acridinones. Arzneimittelforschung. 1993, 43, 480.
   PubMed Web of Science ®Google Scholar
• Csuk, R.; Barthel, A.; Brezesinski, T.; Raschke, C. Synthesis of Dimeric Acridine Derived Antivirals. Med Chem Lett. 2004, 14, 4983. DOI: 10.1016/j.bmcl.2004.07.015.
   PubMed Web of Science ®Google Scholar
• Fang, L.; Appenroth, D.; Decker, M.; Kiehntopf, M.; Roegler, C.; Deufel, T.; Fleck, C.; Peng, S.; Zhang, Y.; Lehmann, J. Synthesis and Biological Evaluation of NO-Donor-Tacrine Hybrids as Hepatoprotective anti-Alzheimer Drug Candidates. J. Med. Chem. 2008, 51, 713. DOI: 10.1021/jm701491k.
   PubMed Web of Science ®Google Scholar
• Burres, N. S.; Sazesh, S.; Gunawardana, G. P.; Clement, J. J. Antitumor Activity and Nucleic Acid Binding Properties of Dercitin, a New Acridine Alkaloid Isolated from a Marine Dercitus Species Sponge. Cancer Res. 1989, 49, 5267.
   PubMed Web of Science ®Google Scholar
• Taraporewala, I. B.; Cessac, J. W.; Chanh, T. C.; Delgado, A. V.; Schinazi, R. F. HIV-1 Neutralization and Tumor Cell Proliferation Inhibition in vitro by Simplified Analogues of pyrido[4,3,2-mn]thiazolo[5,4-b]acridine marine alkaloids. J. Med. Chem. 1992, 35, 2744. DOI: 10.1021/jm00093a005.
   PubMed Web of Science ®Google Scholar
• Tornøe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on Solid Phase: [1,2,3]-triazoles by Regiospecific Copper(i)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides. J. Org. Chem. 2002, 67, 3057. DOI: 10.1021/jo011148j.
   PubMed Web of Science ®Google Scholar
• Reck, F.; Zhou, F.; Girardot, M.; Kern, G.; Eyermann, C. J.; Hales, N. J.; Ramsay, R. R.; Gravestock, M. B . Identification of 4-Substituted 1,2,3-Triazoles as Novel Oxazolidinone Antibacterial Agents with Reduced Activity Against Monoamine Oxidase A. J. Med. Chem. 2005, 48, 499. DOI: 10.1021/jm0400810.
   PubMed Web of Science ®Google Scholar
• Li, W. T.; Wu, W. H.; Tang, C. H.; Tai, R.; Chen, S. T . One-Pot Tandem Copper-Catalyzed Library Synthesis of 1-thiazolyl-1,2,3-triazoles as Anticancer Agents. ACS Comb. Sci. 2011, 13, 72. DOI: 10.1021/co1000234.
   PubMed Web of Science ®Google Scholar
• El-Sherief, H.; Youssif, B.; Bukhari, S.; Abdel-Aziz, M.; Abdel-Rahman, H. M . Novel 1,2,4-Triazole Derivatives as Potential Anticancer Agents: Design, Synthesis, Molecular Docking and Mechanistic Studies. Bioorg. Chem. 2018, 76, 314. DOI: 10.1016/j.bioorg.2017.12.013.
   PubMed Web of Science ®Google Scholar
• Sarigol, D.; Uzgoren-Baran, A.; Tel, B. C.; Somuncuoglu, E. I.; Kazkayasi, I.; Ozadali-Sari, K.; Unsal-Tan, O.; Okay, G.; Ertan, M.; Tozkoparan, B . Novel Thiazolo[3,2-b]-1,2,4-triazoles Derived from Naproxen with Analgesic/Anti-Inflammatory Properties: Synthesis, Biological Evaluation and Molecular Modeling Studies. Bioorg. Med. Chem. 2015, 23, 2518. DOI: 10.1016/j.bmc.2015.03.049.
   PubMed Web of Science ®Google Scholar
• Narsimha, S.; Kumar, N. S.; Swamy, B. K.; Reddy, N. V.; Hussain, S. A.; Rao, M. S . Indole-2-Carboxylic Acid Derived Mono and Bis 1,4-disubstituted 1,2,3-triazoles: Synthesis, Characterization and Evaluation of Anticancer, Antibacterial, and DNA-Cleavage Activities. Bioorg. Med. Chem. Lett. 2016, 26, 1639. DOI: 10.1016/j.bmcl.2016.01.055.
   PubMed Web of Science ®Google Scholar
• Manohar, S.; Khan, S. I.; Rawat, D. S . Synthesis of 4-aminoquinoline-1,2,3-triazole and 4-aminoquinoline-1,2,3-triazole-1,3,5-triazine Hybrids as Potential Antimalarial Agents. Chem. Biol. Drug Des. 2011, 78, 124. DOI: 10.1111/j.1747-0285.2011.01115.x.
   PubMed Web of Science ®Google Scholar
• Gehlhaar, D. K.; Verkhivker, G. M.; Rejto, P. A.; Sherman, C. J.; Fogel, D. R.; Fogel, L. J.; Freer, S. T. Molecular Recognition of the Inhibitor AG-1343 by HIV-1 Protease: Conformationally Flexible Docking by Evolutionary Programming. Chem. Biol. 1995, 2, 317. DOI: 10.1016/1074-5521(95)90050-0.
   PubMed Web of Science ®Google Scholar