Synthesis and antioxidant activity of some pyrazole-based heterocycles using a 2(3H)-furanone building block

References

• 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. DOI: 10.1007/s13738-020-01873-7.
   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. DOI: 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. DOI: 10.1080/00397911.2018.1491995.
   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. DOI: 10.1080/17415993.2021.1878170.
   Web of Science ®Google Scholar
• Kaddah, M. M.; Morsy, A. R.; Fahmi, A. A.; Rizk, S. A.; Ramadan, S. K. 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. Synth. Commun. 2021, 51, 3366. DOI: 10.1080/00397911.2021.1970776.
   Web of Science ®Google Scholar
• Halim, K. N.; Rizk, S. A.; El-Hashash, M. A.; Ramadan, S. K. Straightforward Synthesis, Antiproliferative Screening, and Density Functional Theory Study of Some Pyrazolylpyrimidine Derivatives. J. Heterocycl. Chem. 2021, 58, 636. DOI: 10.1002/jhet.4204.
   Web of Science ®Google Scholar
• Ramadan, S. K.; El‐Ziaty, 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
• 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. DOI: 10.1080/00397911.2020.1765258.
   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. Heterocycl. Chem. 2018, 55, 1942. DOI: 10.1002/jhet.3232.
   Web of Science ®Google Scholar
• El-Helw, E. A. E.; Morsy, A. R.; Hashem, A. I. Evaluation of Some New Heterocycles Bearing 2-Oxoquinolyl Moiety as Immunomodulator against Highly Pathogenic Avian Influenza Virus (H5N8). J. Heterocycl. Chem. 2021, 58, 1003. DOI: 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. DOI: 10.1080/00397911.2020.1731549.
   Web of Science ®Google Scholar
• Ramadan, S. K.; Haleem, D. R.; Abd-Rabboh, H. S.; Gad, N. M.; Abou-Elmagd, W. S. I.; Haneen, D. S. Synthesis, SAR Studies, and Insecticidal Activities of Certain N-Heterocycles Derived from 3-((2-Chloroquinolin-3-yl)Methylene)-5-Phenylfuran-2(3H)-One against Culex pipiens L. larvae. RSC Adv. 2022, 12, 13628. DOI: 10.1039/D2RA02388A.
   PubMed Web of Science ®Google Scholar
• Ramadan, S. K.; Shaban, S. S.; Hashem, A. I. Facile and Expedient Synthesis and anti-Proliferative Activity of Diversely Pyrrolones Bearing 1,3-Diphenylpyrazole Moiety. Synth. Commun. 2020, 50, 185. DOI: 10.1080/00397911.2019.1691737.
   Web of Science ®Google Scholar
• Morsy, A. R.; 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. DOI: 10.1007/s00044-020-02538-z.
   Web of Science ®Google Scholar
• Abbas, S. H.; Abuo-Rahma, G. A.; Abdel-Aziz, M.; Aly, O. M.; Beshr, E. A.; Gamal-Eldeen, A. M. Synthesis, Cytotoxic Activity, and Tubulin Polymerization Inhibitory Activity of New Pyrrol-2(3H)-Ones and Pyridazin-3(2H)-Ones. Bioorg. Chem. 2016, 66, 46–62. DOI: 10.1016/j.bioorg.2016.03.007.
   PubMed Web of Science ®Google Scholar
• (a) Gilchrist, T. L. Heterocyclic Chemistry; Pitman Publishing Ltd: London, 1985; Vol. 195, pp 127.
   Google Scholar
  (b) Ramadan, S. K.; Abou-Elmagd, W. S. I.; Hashem, A. I. Reactions of 2(3H)-Furanones. Synth. Commun. 2019, 49, 3031.
   Google Scholar
• Sawant, P.; Maier Martin, E. Synthesis of Atorvastatin Lactone Linker Constructs for Target Fishing. Tetrahedron 2010, 66, 9738. DOI: 10.1016/j.tet.2010.10.028.
   Web of Science ®Google Scholar
• Valko, M.; Izakovic, M.; Mazur, M.; Rhodes, C. J.; Telser, J. Role of Oxygen Radicals in DNA Damage and Cancer Incidence. Mol. Cell Biochem. 2004, 266, 37–56. DOI: 10.1023/B:MCBI.0000049134.69131.89.
   PubMed Web of Science ®Google Scholar
• Lobo, V.; Patil, A.; Phatak, A.; Chandra, N. Free Radicals, Antioxidants and Functional Foods: Impact on Human Health. Pharmacogn. Rev. 2010, 4, 118–126. DOI: 10.4103/0973-7847.70902.
   PubMedGoogle Scholar
• El-Sayed, A. A.; Ismail, M. F.; Amr, A. E.; Naglah, A. M. Synthesis, Antiproliferative, and Antioxidant Evaluation of 2-Pentylquinazolin-4(3H)-One(Thione) Derivatives with DFT Study. Molecules 2019, 24, 3787. DOI: 10.3390/molecules24203787.
   PubMed Web of Science ®Google Scholar
• Youssef, Y. M.; Azab, M. E.; Elsayed, G. A.; El-Sayed, A. A.; El-Helw, E. A. E. Synthesis and Antiproliferative Screening of Some Heterocycles Derived from 4-((5-Chloro-3-Methyl-1-Phenyl-1H-Pyrazol-4-yl)Methylene)-2-Phenyloxazol-5(4H)-One. Polycycl. Aromat. Compd. 2022. DOI: 10.1080/10406638.2022.2130373.
   Web of Science ®Google Scholar
• Hemdan, M. M.; Fahmy, A. F. M.; Aly, N. F.; Hegazi, I. A.; El-Sayed, A. A. Utility of Phthalimidoacyl Isothiocyanate in Synthesis of Quinazolines, Benzoxazoles, Benzimidazoles, 1,2,4-Triazoles, and Oxatriazepines. Phosphorus Sulfur Silicon Relat. Elem. 2012, 187, 181. DOI: 10.1080/10426507.2011.597804.
   Web of Science ®Google Scholar
• Rizk, S. A.; El‐Sayed, A. A.; Mounier, M. M. Synthesis of Novel Pyrazole Derivatives as Antineoplastic Agent. J. Heterocycl. Chem. 2017, 54, 3358. DOI: 10.1002/jhet.2956.
   Web of Science ®Google Scholar
• Hemdan, M. M.; El-Sayed, A. A. Use of Phthalimidoacetyl Isothiocyanate as a Scaffold in the Synthesis of Target Heterocyclic Systems, and Their Antimicrobial Assessment. Chem. Pharm. Bull. 2016, 64, 483–489. DOI: 10.1248/cpb.c16-00099.
   PubMed Web of Science ®Google Scholar
• Salem, M. S.; El-Helw, E. A. E.; Derbala.; H. A. Russ  . Development of Chromone-Pyrazole-Based Anticancer Agents. Russ. J. Bioorg. Chem. 2020, 46, 77. DOI: 10.1134/S1068162020010094.
   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, 104945.
   PubMed Web of Science ®Google Scholar
  (b) 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. DOI: 10.1016/j.bioorg.2021.104945.
   Web of Science ®Google Scholar
• 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. DOI: 10.1080/17415993.2021.1909591.
   Web of Science ®Google Scholar
• Abdelrahman, A. M.; Fahmi, A. A.; Rizk, S. A.; El-Helw, E. A. E. Synthesis, DFT and Antitumor Activity Screening of Some New Heterocycles Derived from 2,2′-(2-(1,3-Diphenyl-1H-Pyrazol-4-yl)Ethene-1,1-Diyl)Bis(4H-Benzo[d][1,3]Oxazin-4-One). Polycycl. Aromat. Compd. 2023, 43(1), 721. DOI: 10.1080/10406638.2021.2020310.
   Web of Science ®Google Scholar
• Hassaballah, A. I.; Ramadan, S. K.; Rizk, S. A.; El-Helw, E. A. E.; Abdelwahab, S. S. Ultrasonic Promoted Regioselective Reactions of the Novel Spiro 3,1-Benzoxazon-Isobenzofuranone Dye toward Some Organic Base Reagents. Polycycl. Aromat. Compd. 2022. DOI: 10.1080/10406638.2022.2061021.
   Web of Science ®Google Scholar
• Xu, C.-J.; Shi, Y.-Q. Synthesis and Crystal Structure of 5-Chloro-3-Methyl-1-Phenyl-1H-Pyrazole-4-Carbaldehyde. J. Chem. Crystallogr. 2011, 41, 1816. DOI: 10.1007/s10870-011-0178-4.
   Web of Science ®Google Scholar
• Brown, P. M.; Russell, J.; Thomsoon, R. H.; Wylile, A. G. J. Chem. Soc. (c) 1968, 842.
   Google Scholar
• Prieto, P.; Pineda, M.; Aguilar, M. Spectrophotometric Quantation of Antioxidant Capacity through the Formation of a Phosphomolybdenum Complex: Specific Application to the Determination of Vitamin E. Anal. Biochem. 1999, 269, 337. DOI: 10.1006/abio.1999.4019.
   PubMed Web of Science ®Google Scholar
• Ostby, O. B.; Gundersen, L. L.; Rise, F.; Antonsen, O.; Fosnes, K.; Larsen, V.; Bast, A.; Custers, I.; Haenen, G. R. Synthesis of 5-Substituted Pyrrolo[1,2-b]Pyridazines with Antioxidant Properties. Arch. Pharm. 2001, 334, 21. DOI: 10.1002/1521-4184(200101)334:1<21::AID-ARDP21>3.0.CO;2-W.
   PubMed Web of Science ®Google Scholar
• Rice-Evance, C. A.; Miller, N. J.; Paganga, G. Structure-Antioxidant Activity Relationships of Flavonoids and Phenolic Acids. Free Rad. Biol. Med. 1996, 20, 933. DOI: 10.1016/0891-5849(95)02227-9.
   PubMed Web of Science ®Google Scholar
• Imada, I.; Sato, E. F.; Miyamoto, M.; Ichimori, Y.; Minamiyama, Y.; Konaka, R.; Inoue, M. Analysis of Reactive Oxygen Species Generated by Neutrophils Using a Chemiluminescence Probe L-012. Anal. Biochem. 1999, 271, 53–58. DOI: 10.1006/abio.1999.4107.
   PubMed Web of Science ®Google Scholar