Synthesis and biological activity on IBD virus of diverse heterocyclic systems derived from 2-cyano-N'-((2-oxo-1,2-dihydroquinolin-3-yl)methylene)acetohydrazide

References

• Michael, J. P. Quinoline, Quinazoline and Acridone Alkaloids. Nat. Prod. Rep. 2004, 21, 650–668. DOI: https://doi.org/10.1039/b310691h.
   PubMed Web of Science ®Google Scholar
• El-Helw, E. A. E.; Morsy, A. R. I.; Hashem, A. I. Evaluation of Some New Heterocycles Bearing 2-Oxoquinolyl Moiety as Immunomodulator against Highly Pathogenic Avian Influenza Virus (H5N8). J. Heterocyclic Chem. 2021, 58, 1003–1014. DOI: https://doi.org/10.1002/jhet.4233.
   Web of Science ®Google Scholar
• El-Helw, E. A. E.; Hashem, A. I. Synthesis, and Antitumor Activity Evaluation of Some Pyrrolone and Pyridazinone Heterocycles Derived from 3-((2-Oxo-5-(p-Tolyl)Furan-3(2H)-Ylidene)Methyl)Quinolin-2(1H)-One. Synth. Commun. 2020, 50, 1046–1055. DOI: https://doi.org/10.1080/00397911.2020.1731549.
   Web of Science ®Google Scholar
• Xu, M.; Wagerle, T.; Long, J. K.; Lahm, G. P.; Barry, J. D.; Smith, R. M. Insecticidal Quinoline and Isoquinoline Isoxazolines. Bioorg. Med. Chem. Lett. 2014, 24, 4026–4030. DOI: https://doi.org/10.1016/j.bmcl.2014.06.004.
   PubMed Web of Science ®Google Scholar
• Cheng, L.; Cai, P.-P.; Zhang, R.-R.; Han, L.; Tan, C.-X.; Weng, J.-Q.; Xu, T.-M.; Liu, X.-H. Synthesis, and Insecticidal Activity of New Quinoline Derivatives Containing Perfluoropropanyl Moiety. J. Heterocyclic Chem. 2019, 56, 1312–1317. DOI: https://doi.org/10.1002/jhet.3502.
   Web of Science ®Google Scholar
• Morsy, A. R. I.; Ramadan, S. K.; Elsafty, M. M. Synthesis and Antiviral Activity of Some Pyrrolonyl Substituted Heterocycles as Additives to Enhance Inactivated Newcastle Disease Vaccine. Med. Chem. Res. 2020, 29, 979–988. DOI: https://doi.org/10.1007/s00044-020-02538-z.
   Web of Science ®Google Scholar
• Alam, M.; Sarkar, P.; Husain, A.; Marella, A.; Zaman, M. S.; Akhter, M.; Shaharyar, M.; Alam, O.; Azam, F. Synthesis of Quinoline-Attached Furan-2(3H)-Ones Having anti-Inflammatory and Antibacterial Properties with Reduced Gastro-Intestinal Toxicity and Lipid Peroxidation. J. Serb. Chem. Soc. 2011, 76, 1617–1626. DOI: https://doi.org/10.2298/JSC110131142A.
   Web of Science ®Google Scholar
• El-Gazzar, A. B.; Hafez, H. N.; Nawwar, G. A. New Acyclic Nucleosides Analogues as Potential Analgesic, anti-Inflammatory, anti-Oxidant and anti-Microbial Derived from Pyrimido[4,5-b]Quinolines. Eur. J. Med. Chem. 2009, 44, 1427–1436. DOI: https://doi.org/10.1016/j.ejmech.2008.09.030.
   PubMed Web of Science ®Google Scholar
• Gao, F.; Wang, P.; Yang, H.; Miao, Q.; Ma, L.; Lu, G. Recent Developments of Quinolone-Based Derivatives and Their Activities against Escherichia coli. Eur. J. Med. Chem. 2018, 157, 1223–1248. DOI: https://doi.org/10.1016/j.ejmech.2018.08.095.
   PubMed Web of Science ®Google Scholar
• Kategaonkar, A. H.; Pokalwar, R. U.; Sonar, S. S.; Gawali, V. U.; Shingate, B. B.; Shingare, M. S. Synthesis, in Vitro Antibacterial and Antifungal Evaluations of New α-Hydroxyphosphonate and New α-Acetoxyphosphonate Derivatives of Tetrazolo[1,5-a] Quinoline. Eur. J. Med. Chem. 2010, 45, 1128–1132. DOI: https://doi.org/10.1016/j.ejmech.2009.12.013.
   PubMed Web of Science ®Google Scholar
• Mandal, S.; Bhuyan, S.; Jana, S.; Hossain, J.; Chhetri, K.; Roy, B. G. Efficient Visible Light Mediated Synthesis of Quinolin-2(1H)-Ones from Quinoline N-Oxides. Green Chem. 2021, 23, 5049–5055. DOI: https://doi.org/10.1039/D1GC01460A.
   Web of Science ®Google Scholar
• Xie, L.-Y.; Qu, J.; Peng, S.; Liu, K.-J.; Wang, Z.; Ding, M.-H.; Wang, Y.; Cao, Z.; He, W.-M. Selectfluor-Mediated Regioselective Nucleophilic Functionalization of N-Heterocycles under Metal- and Base-Free Conditions. Green Chem. 2018, 20, 760–764. DOI: https://doi.org/10.1039/C7GC03106H.
   Web of Science ®Google Scholar
• Xie, L.-Y.; Duan, Y.; Lu, L.-H.; Li, Y.-J.; Peng, S.; Wu, C.; Liu, K.-J.; Wang, Z.; He, W.-M. Fast, Base-Free and Aqueous Synthesis of Quinolin-2(1H)-Ones under Ambient Conditions. ACS Sustainable Chem. Eng. 2017, 5, 10407–10412. DOI: https://doi.org/10.1021/acssuschemeng.7b02442.
   Web of Science ®Google Scholar
• El-Naggar, A. M.; Ramadan, S. K. Efficient Synthesis of Some Pyrimidine and Thiazolidine Derivatives Bearing Quinoline Scaffold under Microwave Irradiation. Synth. Commun. 2020, 50, 2188–2198. DOI: https://doi.org/10.1080/00397911.2020.1769673.
   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: https://doi.org/10.1016/j.ejmech.2009.11.036.
   PubMed Web of Science ®Google Scholar
• Forlani, L.; Cristoni, G.; Boga, C.; Todesco, P. E.; Vecchio, E. D.; Selva, S.; Monari, M. Reinvestigation of the Tautomerism of Some Substituted 2-Hydroxypyridines. ARKIVOC 2002, 2002, 198–215. DOI: https://doi.org/10.3998/ark.5550190.0003.b18.
   Web of Science ®Google Scholar
• Rao, H. S. P.; Senthilkumar, S. P. Review on the Synthesis of 8-Azasteroids. Curr. Org. Chem. 2004, 8, 1521–1528. DOI: https://doi.org/10.2174/1385272043369881.
   Web of Science ®Google Scholar
• Uscumlic, G.; Mijin, D.; Valentic, N.; Vajs, V.; Susic, B. Substituent and Solvent Effects on the UV/Vis Absorption Spectra of 5-(4-Substituted Arylazo)-6-Hydroxy-4-Methyl-3-Cyano-2-Pyridones. Chem. Phys. Lett. 2004, 397, 148–153. DOI: https://doi.org/10.1016/j.cplett.2004.07.057.
   Web of Science ®Google Scholar
• Balamurugan, V.; Kataria, J. M. Economically Important Non-Oncogenic Immunosuppressive Viral Diseases of Chicken-Current Status. Vet. Res. Commun. 2006, 30, 541–566. DOI: https://doi.org/10.1007/s11259-006-3278-4.
   PubMed Web of Science ®Google Scholar
• Lütticken, D. Viral Diseases of the Immune System and Strategies to Control Infectious Bursal Disease by Vaccination. Acta Vet. Hung. 1997, 45, 239–249.
   PubMed Web of Science ®Google Scholar
• Sharma, J. M. Introduction to Poultry Vaccines and Immunity. Adv. Vet. Med. 1999, 41, 481–494. DOI: https://doi.org/10.1016/s0065-3519(99)80036-6.
   PubMedGoogle Scholar
• Rauf, A. Persistence, Distribution and Immunopathogenesis of Infectious Bursal Disease Virus in Chickens; The Ohio State University: Columbus, OH: OhioLINK Electronic Theses and Dissertations Center, 2011.
   Google Scholar
• Ingrao, F.; Rauw, F.; Lambrecht, B.; Van den Berg, T. Infectious Bursal Disease: A Complex Host-Pathogen Interaction. Dev. Comp. Immunol. 2013, 41, 429–438. DOI: https://doi.org/10.1016/j.dci.2013.03.017.
   PubMed Web of Science ®Google Scholar
• Beenish, Z.; Khan, M. U. R.; Aslam, A.; Durrani, A. Z.; Alam, S.; Saleem, M. H.; Mehmood, K. Effect of a Herbal Supplement Livol on the Growth Performance and Antibody Response Against Infectious Bursal Disease Virus in Broiler Chicks. Pakistan J. Zool. 2013, 45, 1387.
   Web of Science ®Google Scholar
• Cosgrove, A. S. An Apparently New Disease of Chickens – Avian Nephrosis. Avian Dis. 1962, 6, 385. DOI: https://doi.org/10.2307/1587909.
   Web of Science ®Google Scholar
• Sharma, J. M.; Dohms, J. E.; Metz, A. L. Comparative Pathogenesis of Serotype I and Variant Serotype 1 Isolates of Infectious Bursal Disease Virus and Their Effect on Humoral and Cellular Immune Competence of Specific Pathogen-Free Chickens. Avian Dis. 1989, 33, 112–124. DOI: https://doi.org/10.2307/1591076.
   PubMed Web of Science ®Google Scholar
• Maclachlan, N. J.; Dubovi, E. J. Birnaviridae. In Fenner’s Veterinary Virology, 8th ed.; Maclachlan, N. J., Dubovi, E. J., Eds.; Elsevier: Oxford, UK, 2011; pp 293–298.
   Google Scholar
• El-Helw, E. A. E.; El-Badawy, A. A. Synthesis of Chromenone, Pyrimidinone, Thiazoline and Quinolone Derivatives as Prospective Antitumor Agents. J. Heterocycl. Chem. 2020, 57, 2354. DOI: https://doi.org/10.1002/jhet.3948.
   Web of Science ®Google Scholar
• Fadda, A. A.; Bondock, S.; Rabie, R.; Etman, H. A. Cyanoacetamide Derivatives as Synthons in Heterocyclic Synthesis. Turk. J. Chem. 2008, 32, 259.
   Web of Science ®Google Scholar
• Ramadan, S. K.; El-Helw, E. A. E.; Azab, M. E. 2-Cyano-N′-[(1,3-Diphenyl-1H-Pyrazol-4-yl)Methylidene]Acetohydrazide in the Synthesis of Nitrogen Heterocycles. Russ. J. Org. Chem. 2019, 55, 1940–1945. DOI: https://doi.org/10.1134/S1070428019120224.
   Web of Science ®Google Scholar
• Huang, W.; Li, J.; Tang, J.; Liu, H.; Shen, J.; Jiang, H. Microwave‐Assisted Synthesis of 2-Amino-Thiophene-3-Carboxylic Derivatives under Solvent-Free Conditions. Synth. Commun. 2005, 35, 1351–1357. DOI: https://doi.org/10.1081/SCC-200057268.
   Web of Science ®Google Scholar
• Ibrahim, S. N.; Abed, M. N.; Kandeel, Z. E. Nitriles in Heterocyclic Synthesis: A New Approach for the Synthesis of Thiazinones. Heterocycles 1984, 22, 1677. DOI: https://doi.org/10.3987/R-1984-08-1677.
   Web of Science ®Google Scholar
• Youssef, A. S. A.; Hemdan, M. M.; El-Mariah, F. A.; Hashem, H. E. Synthesis of Some Quinazolinone Derivatives Functionalized with N-3 Heterocyclic Side Chain. J. Heterocyclic Chem. 2018, 55, 1626–1633. DOI: https://doi.org/10.1002/jhet.3197.
   Web of Science ®Google Scholar
• Halim, K. N. M.; Ramadan, S. K.; Rizk, S. A.; El-Hashash, M. A. Synthesis, DFT Study, Molecular Docking, and Insecticidal Evaluation of Some Pyrazole-Based Tetrahydropyrimidine Derivatives. Synth. Commun. 2020, 50, 1159–1175. DOI: https://doi.org/10.1080/00397911.2020.1720739.
   Web of Science ®Google Scholar
• Kaddah, M. M.; Fahmi, A. A.; Kamel, M. M.; Ramadan, S. K.; Rizk, S. A. Synthesis, Characterization, Computational Chemical Studies and Antiproliferative Activity of Some Heterocyclic Systems Derived from 3-(3-(1,3-Diphenyl-1H-Pyrazol-4-yl)Acryloyl)-2H-Chromen-2-One. Synth. Commun. 2021, 51, 1798–1813. DOI: https://doi.org/10.1080/00397911.2021.1904991.
   Web of Science ®Google Scholar
• Ramadan, S. K.; Abou-Elmagd, W. S. I. Synthesis and anti H5N1 Activities of Some Novel Fused Heterocycles Bearing Pyrazolyl Moiety. Synth. Commun. 2018, 48, 2409–2419. DOI: https://doi.org/10.1080/00397911.2018.1491995.
   Web of Science ®Google Scholar
• Ramadan, S. K.; Elziaty, A. K.; El-Helw, E. A. E. Synthesis and Antioxidant Evaluation of Some Heterocyclic Candidates from 3-(1,3-Diphenyl-1H-Pyrazol-4-yl)-2-(4-Oxo-4H-Benzo[d][1,3]Oxazin-2-yl)Propenonitrile. Synth. Commun. 2021, 51, 1272.
   Web of Science ®Google Scholar
• (a) Ramadan, S. K.; Ibrahim, N. A.; El-Kaed, S. A.; El-Helw, E. A. E. New Potential Fungicides Pyrazole-Based Heterocycles Derived from 2-Cyano-3-(1,3-Diphenyl-1H -Pyrazol-4-yl)Acryloyl Isothiocyanate. J. Sulfur Chem. 2021, 42, 529–546. DOI: https://doi.org/10.1080/17415993.2021.1909591.
   Web of Science ®Google Scholar
  (b) Salem, M. S.; El-Helw, E. A. E.; Derbala, H. A. Development of Chromone-Pyrazole-Based Anticancer Agents. Russ. J. Bioorg. Chem. 2020, 46, 77. DOI: https://doi.org/10.1080/17415993.2021.1909591.
   Web of Science ®Google Scholar
• (a) Ghareeb, E. A.; Mahmoud, N. F. H.; El-Bordany, E. A.; El-Helw, E. A. E.; Synthesis, DFT, and Eco-Friendly Insecticidal Activity of Some N-Heterocycles Derived from 4-((2-Oxo-1,2-Dihydroquinolin-3-yl)Methylene)-2-Phenyloxazol-5(4H)-One. Bioorg. Chem. 2021, 112, 1. 104945. DOI: https://doi.org/10.1016/j.bioorg.2021.104945.
   PubMed Web of Science ®Google Scholar
  (b) El-Helw, E. A. E.; Gado, M. M.; El-Ziaty, A. K. Synthesis and anti-Rotavirus Activity of Some Nitrogen Heterocycles Integrated with Pyrazole Scaffold. J. Iran. Chem. Soc. 2020, 17, 1479–1492. DOI: https://doi.org/10.1007/s13738-020-01873-7.
   Web of Science ®Google Scholar
• El-Badawy, A. A.; Elgubbi, A. S.; El-Helw, E. A. E. Acryloyl Isothiocyanate Skeleton as a Precursor for Synthesis of Some Novel Pyrimidine, Triazole, Triazepine, Thiadiazolopyrimidine and Acylthiourea Derivatives as Antioxidant Agents. J. Sulfur Chem. 2021, 42, 295–307. DOI: https://doi.org/10.1080/17415993.2021.1878170.
   Web of Science ®Google Scholar
• Ramadan, S. K.; Sallam, H. A. Synthesis, Spectral Characterization, Cytotoxic, and Antimicrobial Activities of Some Novel Heterocycles Utilizing 1,3-Diphenylpyrazole-4-Carboxaldehyde Thiosemicarbazone. J. Heterocyclic Chem. 2018, 55, 1942–1954. DOI: https://doi.org/10.1002/jhet.3232.
   Web of Science ®Google Scholar
• Ramadan, S. K.; Elrazaz, E. Z.; Abouzid, K. A. M.; El-Naggar, A. M. Design, Synthesis and in Silico Studies of New Quinazolinone Derivatives as Antitumor PARP-1 Inhibitors. RSC Adv. 2020, 10, 29475–29492. DOI: https://doi.org/10.1039/D0RA05943A.
   PubMed Web of Science ®Google Scholar
• Ramadan, S. K.; El-Helw, E. A. E.; Sallam, H. A. Cytotoxic and Antimicrobial Activities of Some Novel Heterocycles Employing 6-(1,3-Diphenyl-1H-Pyrazol-4-yl)-4-Oxo-2-Thioxo-1,2,3,4-Tetrahydropyrimidine-5-Carbonitrile. Heterocycl. Commun. 2019, 25, 107–115. DOI: https://doi.org/10.1515/hc-2019-0008.
   Web of Science ®Google Scholar
• (a) Ramadan, S. K.; El-Ziaty, A. K.; Ali, R. S.; Synthesis, Antiproliferative Activity, and Molecular Docking of Some N-Heterocycles Bearing a Pyrazole Scaffold against Liver and Breast Tumors. J. Heterocyclic Chem. 2021, 58, 5. 290–304. DOI: https://doi.org/10.1002/jhet.4168.
   Web of Science ®Google Scholar
  (b) Sallam, H. A.; Elgubbi, A. S.; El-Helw, E. A. E. Synthesis and Antioxidant Screening of New 2-Cyano-3-(1,3-Diphenyl-1H-Pyrazol-4-yl)Acryloyl Amide Derivatives and Some Pyrazole-Based Heterocycles. Synth. Commun. 2020, 50, 2066–2077. DOI: https://doi.org/10.1080/00397911.2020.1765258.
   Web of Science ®Google Scholar
• Ramesh, E.; Sree Vidhya, T. K.; Raghunathan, R. Indium Chloride/Silica Gel Supported Synthesis of Pyrano/Thiopyranoquinolines through Intramolecular Imino Diels-Alder Reaction Using Microwave Irradiation. Tetrahedron Lett. 2008, 49, 2810–2814. DOI: https://doi.org/10.1016/j.tetlet.2008.02.128.
   Web of Science ®Google Scholar
• Zhang, Y.; Fang, Y.; Liang, H.; Wang, H.; Hu, K.; Liu, X.; Yi, X.; Peng, Y. Synthesis and Antioxidant Activities of 2-Oxo-Quinoline-3-Carbaldehyde Schiff-Base Derivatives. Bioorg. Med. Chem. Lett. 2013, 23, 107–111. DOI: https://doi.org/10.1016/j.bmcl.2012.11.006.
   PubMed Web of Science ®Google Scholar
• Reed, L. J.; Muench, H. A Simple Method of Estimating Fifty Percent End Point. Am. J. Hyg. 1938, 27, 493.
   Google Scholar
• Infectious Bursal Disease. In OIE Terrestrial Manual; World Organisation For Animal Health: Paris, France, 2008.
   Google Scholar
• Singh, N. K.; Dey, S.; Madhan, M. C.; Kataria, J. M.; Vakharia, V. N. Evaluation of Four Enzyme Linked Immunosorbent Assays for the Detection of Antibodies to Infectious Bursal Disease in Chickens. J. Virol. Methods. 2010, 165, 277–282. DOI: https://doi.org/10.1016/j.jviromet.2010.02.008.
   PubMed Web of Science ®Google Scholar