Synthesis and anticancer activity of oxazolo and oxazinoquinolinone derivatives

References

• DeVita, R. J.; Goulet, M. T.; Wyvratt, M. J.; Fisher, M. H.; Lo, J.-L.; Yang, Y. T.; Cheng, K.; Smith, R. G. Investigation of the 4-O-Alkylamine Substituent of Non-Peptide Quinolone GnRH Receptor Antagonists. Bioorg. Med. Chem. Lett. 1999, 9, 2621–2624. DOI: 10.1016/S0960-894X(99)00447-3.
   PubMed Web of Science ®Google Scholar
• McQuaid, L. A.; Smith, E. C.; Lodge, D.; Pralong, E.; Wikel, J. H.; Calligaro, D. O.; O'Malley, P. J. 3-Phenyl-4-Hydroxyquinolin-2(1H)-Ones: Potent and Selective Antagonists at the Strychnine-Insensitive Glycine Site on the N-methyl-D-Aspartate Receptor Complex. J. Med. Chem. 1992, 35, 3423–3425. DOI: 10.1021/jm00096a019.
   PubMed Web of Science ®Google Scholar
• Fuchigami, T.; Haradahira, T.; Fujimoto, N.; Nojiri, Y.; Mukai, T.; Yamamoto, F.; Okauchi, T.; Maeda, J.; Suzuki, K.; Suhara, T.; et al. Development of N-[11C]Methylamino 4-Hydroxy-2(1H)-Quinolone Derivatives as PET Radioligands for the Glycine-Binding Site of NMDA Receptors. Bioorg. Med. Chem. 2009, 17, 5665–5675. DOI: 10.1016/j.bmc.2009.06.014.
   PubMed Web of Science ®Google Scholar
• Rowley, M.; Kulagowski, J. J.; Watt, A. P.; Rathbone, D.; Stevenson, G. I.; Carling, R. W.; Baker, R.; Marshall, G. R.; Kemp, J. A.; Foster, A. C.; et al. Effect of Plasma Protein Binding on In Vivo Activity and Brain Penetration of Glycine/NMDA Receptor Antagonists. J. Med. Chem. 1997, 40, 4053–4068. DOI: 10.1021/jm970417o.
   PubMed Web of Science ®Google Scholar
• Leeson, P. D.; Baker, R.; Carling, R. W.; Kulagowski, J. J.; Mawer, I. M.; Ridgill, M. P.; Rowley, M.; Smith, J. D.; Stansfield, I.; Stevenson, G. I.; et al. Amino Acid Bioisosteres: Design of 2-Quinolone Derivatives as Glycine-Site N-methyl-D-Aspartate Receptor Antagonists. Bioorg. Med. Chem. Lett. 1993, 3, 299–304. DOI: 10.1016/S0960-894X(01)80897-0.
   Web of Science ®Google Scholar
• Sarveswari, S.; Vijayakumar, V.; Siva, R.; Priya, R. Synthesis of 4-Hydroxy-2(1H)-Quinolone Derived Chalcones, Pyrazolines and Their Antimicrobial, in Silico Antimalarial Evaluations. Appl. Biochem. Biotechnol. 2015, 175, 43–64. DOI: 10.1007/s12010-014-1256-9.
   PubMed Web of Science ®Google Scholar
• Patel, R. V.; Kumari, P.; Rajani, D. P.; Chikhalia, K. H. Synthesis, Characterization and Pharmacological Activities of 2-[4-Cyano-(3-Trifluoromethyl)Phenyl Amino)]-4-(4-Quinoline/Coumarin-4-Yloxy)-6-(Fluoropiperazinyl)-s-Triazines. J. Fluorine Chem. 2011, 132, 617–627. DOI: 10.1016/j.jfluchem.2011.06.021.
   Web of Science ®Google Scholar
• Krishna, A.; Vijayakumar, V.; Sarveswari, S. Chemistry Select 2020, 5, 7967–7972.
   Google Scholar
• Sarveswari, S.; Vijayakumar, V. Int. J. Chem. Tech. Res. 2015, 8, 782–788.
   Google Scholar
• Arya, K.; Agarwal, M. Microwave Prompted Multigram Synthesis, Structural Determination, and Photo-Antiproliferative Activity of Fluorinated 4-Hydroxyquinolinones. Bioorg. Med. Chem. Lett. 2007, 17, 86–93. DOI: 10.1016/j.bmcl.2006.09.082.
   PubMed Web of Science ®Google Scholar
• Abass, M.; Mostafa, B. B. Synthesis and Evaluation of Molluscicidal and Larvicidal Activities of Some Novel Enaminones Derived from 4-Hydroxyquinolinones: Part IX. Bioorg. Med. Chem. 2005, 13, 6133–6144. DOI: 10.1016/j.bmc.2005.06.038.
   PubMed Web of Science ®Google Scholar
• Roussaki, M.; Hall, B.; Lima, S. C.; da Silva, A. C.; Wilkinson, S.; Detsi, A. Synthesis and Anti-Parasitic Activity of a Novel Quinolinone–Chalcone Series. Bioorg. Med. Chem. Lett. 2013, 23, 6436–6441. DOI: 10.1016/j.bmcl.2013.09.047.
   PubMed Web of Science ®Google Scholar
• Sherlock, M. H.; Kaminski, J. J.; Tom, W. C.; Lee, J. F.; Wong, S.-C.; Kreutner, W.; Bryant, R. W.; McPhail, A. T. Antiallergy Agents. 1. Substituted 1,8-Naphthyridin-2(1H)-Ones as Inhibitors of SRS-A Release. J. Med. Chem. 1988, 31, 2108–2121. DOI: 10.1021/jm00119a010.
   PubMed Web of Science ®Google Scholar
• Saylam, A.; Seferoğlu, Z.; Ertan, N. Azo-8-Hydroxyquinoline Dyes: The Synthesis, Characterizations and Determination of Tautomeric Properties of Some New Phenyl- and Heteroarylazo-8-Hydroxyquinolines. J. Mol. Liq. 2014, 195, 267–276. DOI: 10.1016/j.molliq.2014.02.027.
   Web of Science ®Google Scholar
• Rufchahi, E. O. M. Chin. Chem. Lett. 2010, 21, 542–546. DOI: 10.1016/j.cclet.2010.01.017.
   Web of Science ®Google Scholar
• Rufchahi, E. O. M.; Ghanadzadeh, A. A Study of Solvatochromism in Diazonium Coupling Products of 6-Flouro 4-Hydroxyl-2-Quinolone. J. Mol. Liq. 2011, 160, 160–165. DOI: 10.1016/j.molliq.2011.03.011.
   Web of Science ®Google Scholar
• Rufchahi, E. O. M.; Gilani, A. G. Synthesis, Characterization and Spectroscopic Properties of Some New Azo Disperse Dyes Derived from 4-Hydroxybenzo[h]Quinolin-2-(1H)-One as a New Synthesized Enol Type Coupling Component. Dyes Pigm. 2012, 95, 632–638. DOI: 10.1016/j.dyepig.2012.06.008.
   Web of Science ®Google Scholar
• Rufchahi, E. O. M.; Pouramir, H.; Yazdanbakhsh, M. R.; Yousefi, H.; Bagheri, M.; Rassa, M. Novel Azo Dyes Derived from 8-Methyl-4-Hydroxyl-2-Quinolone: Synthesis, UV–Vis Studies and Biological Activity. Chin. Chem. Lett. 2013, 24, 425–428. DOI: 10.1016/j.cclet.2013.03.002.
   Web of Science ®Google Scholar
• Rufchahi, E. O. M.; Mohammadinia, M. 6-Butyl-4-Hydroxyquinolin-2-(1H)-One as an Enol Type Coupling Component for the Synthesis of Some New Azo Disperse Dyes. J. Mol. Liq. 2014, 199, 393–400. DOI: 10.1016/j.molliq.2014.09.039.
   Web of Science ®Google Scholar
• Asghari, S.; Ramezani, S.; Mohseni, M. Synthesis and Antibacterial Activity of Ethyl 2-Amino-6-Methyl-5-Oxo-4-Aryl-5,6-Dihydro-4H-Pyrano[3,2-c]Quinoline-3-Carboxylate. Chin. Chem. Lett. 2014, 25, 431–434. DOI: 10.1016/j.cclet.2013.12.010.
   Web of Science ®Google Scholar
• Khaleghi-Abbasabadi, M.; Azarifar, D. Magnetic Fe3O4-Supported Sulfonic Acid-Functionalized Graphene Oxide (Fe3O4@GO-naphthalene-SO3H): a Novel and Recyclable Nanocatalyst for Green One-Pot Synthesis of 5-Oxo-Dihydropyrano[3,2-c]Chromenes and 2-Amino-3-Cyano-1,4,5,6-Tetrahydropyrano[3,2-c]Quinolin-5-Ones. Res. Chem. Intermed. 2019, 45, 2095–2118. DOI: 10.1007/s11164-018-03722-y.
   Web of Science ®Google Scholar
• Salnikova, T. V.; Sabitov, A. A.; Dmitriev, M. V.; Maslivets, A. N.; Rubin, M. Substrate-Dependent Regiodivergent Three-Component Condensation of 1H-Pyrrole-2,3-Diones, Malononitrile and 4-Hydroxyquinolin-2(1H)-Ones. Tetrahedron 2021, 88, 132129–132138. DOI: 10.1016/j.tet.2021.132129.
   Web of Science ®Google Scholar
• Ishida, T.; Kikuchi, S.; Yamada, T. Efficient Preparation of 4-Hydroxyquinolin-2(1H)-One Derivatives with Silver-Catalyzed Carbon Dioxide Incorporation and Intramolecular Rearrangement. Org. Lett. 2013, 15, 3710–3713. DOI: 10.1021/ol401571r.
   PubMed Web of Science ®Google Scholar
• Guo, C.-X.; Zhang, W.-Z.; Liu, S.; Lu, X.-B. Cu(i)-Catalyzed Chemical Fixation of CO2 with 2-Alkynylaniline into 4-Hydroxyquinolin-2(1H)-One. Catal. Sci. Technol. 2014, 4, 1570–1577. DOI: 10.1039/c3cy00858d.
   Web of Science ®Google Scholar
• Zhang, S.-L.; Huang, Z.-S.; Li, Y.-M.; Chan, A. S. C.; Gu, L.-Q. Synthesis of Zwitterionic 4-Hydroxy-2(1H)-Quinolinone Derivatives. Tetrahedron 2008, 64, 4403–4407. DOI: 10.1016/j.tet.2008.02.052.
   Web of Science ®Google Scholar
• Okamoto, T.; Kimura, E.; Iwasaki, S.; Yamamoto, K. Studies on Reaction of Alkali-Fusion of Haloquinolones via Aryne Intermediates. Chem. Pharm. Bull. 1969, 17, 2083–2087. DOI: 10.1248/cpb.17.2083.
   Web of Science ®Google Scholar
• Gradillas, A.; Lopez, B.; Brana , Sancho, I.; Perez-Garkia, C.; Alguacil, L. F. Arzneim.-Forsch./Drug Res. 2005, 55, 725–729.
   PubMed Web of Science ®Google Scholar
• Zhang, F.; Chapman, K. T.; Schleif, W. A.; Olsen, D. B.; Stahlhut, M.; Rutkowski, C. A.; Kuo, L. C.; Jin, L.; Lin, J. H.; Emini, E. A.; Tata, J. R. The Design, Synthesis and Evaluation of Novel HIV-1 Protease Inhibitors with High Potency against PI-Resistant Viral Strains. Bioorg. Med. Chem. Lett. 2003, 13, 2573–2576. DOI: 10.1016/S0960-894X(03)00474-8.
   PubMed Web of Science ®Google Scholar
• Minhas, G. S.; Pilch, D. S.; Kerrigan, J. E.; La Voie, E. J.; Rice, J. E. Synthesis and G-Quadruplex Stabilizing Properties of a Series of Oxazole-Containing Macrocycles. Bioorg. Med. Chem. Lett. 2006, 16, 3891–3895. DOI: 10.1016/j.bmcl.2006.05.038.
   PubMed Web of Science ®Google Scholar
• Abdel-Kader, D.; Abass, M. Synthesis of Some Oxazolo and Oxazinopyrano[3,2‐c] Quinolines and Their Antitumor Activity. J. Heterocyclic Chem. 2020, 57, 2480–2488. DOI: 10.1002/jhet.3963.
   Web of Science ®Google Scholar
• Bheemappa, E.; Aswathanarayanappa, C.; Bodke, Y. D.; Peethamber, S. K. Der. Pharma Chem. 2014, 6, 220–227.
   Google Scholar
• García, J. J. S.; Flores-Alamo, M.; Martínez-Klimova, E.; Apan, T. R.; Klimova, E. I. Diferrocenyl(Areno)Oxazoles, Spiro(Arenooxazole)Cyclopropenes, Quinolines and Areno[1,4-]Oxazines: Synthesis, Characterization and Study of Their Antitumor Activity. J. Organomet. Chem. 2018, 867, 312–322. DOI: 10.1016/j.jorganchem.2018.01.026.
   Web of Science ®Google Scholar
• Regal, M. K. A.; Shabana, S. S.; El-Metwally, S. A. Reactivity and Anticancer Assessment of 4-Hydroxyquinoline Derivatives. Russ. J. Org. Chem. 2020, 56, 307–314. DOI: 10.1134/S1070428020020219.
   Web of Science ®Google Scholar
• Voight, E. A.; Daanen, J. F.; Kort, M. E. Synthesis of Oxazolo[4,5-c]Quinoline TRPV1 Antagonists. J. Org. Chem. 2010, 75, 8713–8715. DOI: 10.1021/jo101938b.
   PubMed Web of Science ®Google Scholar
• Eswaran, S.; Adhikari, A. V.; Kumar, R. A. New 1,3-Oxazolo[4,5-c]Quinoline Derivatives: synthesis and Evaluation of Antibacterial and Antituberculosis Properties. Eur. J. Med. Chem. 2010, 45, 957–966. DOI: 10.1016/j.ejmech.2009.11.036.
   PubMed Web of Science ®Google Scholar
• Buckle, D. R.; Cantello, B. C. C.; Smith, H.; Spicer, B. A. 4-hydroxy-3-Nitro-2-Quinolones and Related Compounds as Inhibitors of Allergic Reactions. J. Med. Chem. 1975, 18, 726–732. DOI: 10.1021/jm00241a017.
   PubMed Web of Science ®Google Scholar
• Roschger, P.; Fiala, W.; Stadlbauer, W. Nucleophilic Substitution and Ring Closure Reactions of 4-Chloro-3-Nitro-2-Quinolones. J. Heterocycl. Chem. 1992, 29, 225–231. DOI: 10.1002/jhet.5570290141.
   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. DOI: 10.1016/0022-1759(83)90303-4.
   PubMed Web of Science ®Google Scholar
• Gomha, S. M.; Riyadh, S. M.; Mahmmoud, E. A.; Elaasser, M. M. Heterocycles 2015, 91, 1227–1243.
   Web of Science ®Google Scholar
• Jedhe, G. S.; Paul, D.; Gonnade, R. G.; Santra, M. K.; Hamel, E.; Nguyen, T. L.; Sanjayan, G. J. Correlation of Hydrogen-Bonding Propensity and Anticancer Profile of Tetrazole-Tethered Combretastatin Analogues. Bioorg. Med. Chem. Lett. 2013, 23, 4680–4684. DOI: 10.1016/j.bmcl.2013.06.004.
   PubMed Web of Science ®Google Scholar