132
Views
6
CrossRef citations to date
0
Altmetric
Research Articles

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)

, , ORCID Icon & ORCID Icon
Pages 721-739 | Received 18 Sep 2021, Accepted 05 Dec 2021, Published online: 24 Dec 2021

References

  • E. A. E. El-Helw, M. M. Gado, and A. K. El-Ziaty, “Synthesis and Anti-Rotavirus Activity of Some Nitrogen Heterocycles Integrated with Pyrazole Scaffold,” Journal of the Iranian Chemical Society 17, no. 6 (2020): 1479–92.
  • S. K. Ramadan, N. A. Ibrahim, S. A. El-Kaed, and E. A. E. El-Helw, “New Potential Fungicides Pyrazole-Based Heterocycles Derived from 2-Cyano-3-(1,3-Diphenyl-1H-Pyrazol-4-yl) Acryloyl Isothiocyanate,” Journal of Sulfur Chemistry 42, no. 5 (2021): 529–46.
  • A. R. I. Morsy, S. K. Ramadan, and M. M. Elsafty, “Synthesis and Antiviral Activity of Some Pyrrolonyl Substituted Heterocycles as Additives to Enhance Inactivated Newcastle Disease Vaccine,” Medicinal Chemistry Research 29, no. 6 (2020): 979–88.
  • S. K. Ramadan, A. K. El-Ziaty, and E. A. E. El-Helw, “Synthesis and Antioxidant Evaluation of Some Heterocyclic Candidates from 3-(1,3-Diphenyl-1H-Pyrazol-4-yl)-2-(4-Oxo-4H-Benzod][1,3]Oxazin-2-yl)Propenonitrile.” Synthetic Communications 51, no. 8 (2021): 1272.
  • H. A. Sallam, A. S. Elgubbi, and E. A. E. El-Helw, “Synthesis and Antioxidant Screening of New 2-Cyano-3-(1,3-Diphenyl-1H-Pyrazol-4-yl)Acryloyl Amide Derivatives and Some Pyrazole-Based Heterocycles,” Synthetic Communications. 50, no. 13 (2020): 2066–77.
  • E. A. E. El-Helw, and A. A. El-Badawy, “Synthesis of Chromenone, Pyrimidinone, Thiazoline, and Quinolone Derivatives as Prospective Antitumor Agents,” Journal of Heterocyclic Chemistry 57, no. 6 (2020): 2354.
  • K. Karrouchi, S. Radi, Y. Ramli, J. Taoufik, Y. N. Mabkhot, F. A. Al-Aizari, and M. Ansar, “Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review,” Molecules 23, no. 1 (2018): 134.
  • S. K. Ramadan, E. A. E. El-Helw, and H. A. Sallam, “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,” Heterocyclic Communications 25, no. 1 (2019): 107–15.
  • K. N. M. Halim, S. A. Rizk, M. A. El-Hashash, and S. K. Ramadan, “Straightforward Synthesis, Antiproliferative Screening, and Density Functional Theory Study of Some Pyrazolylpyrimidine Derivatives,” Journal of Heterocyclic Chemistry 58, no. 2 (2021): 636–45.
  • M. M. Kaddah, A. A. Fahmi, M. M. Kamel, S. K. Ramadan, and S. A. Rizk, “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,” Synthetic Communications 51, no. 12 (2021): 1798–813.
  • S. K. Ramadan, A. K. El-Ziaty, and R. S. Ali, “Synthesis, Antiproliferative Activity, and Molecular Docking of Some N-Heterocycles Bearing a Pyrazole Scaffold against Liver and Breast Tumors,” Journal of Heterocyclic Chemistry 58, no. 1 (2021): 290–304.
  • S. K. Ramadan, K. N. M. Halim, S. A. Rizk, and M. A. El-Hashash, “Cytotoxic Activity and Density Functional Theory Studies of Some 1,3-Diphenylpyrazolyltetrahydropyrimidine Derivatives,” Journal of the Iranian Chemical Society 17, no. 7 (2020): 1575–89.
  • K. N. M. Halim, S. K. Ramadan, S. A. Rizk, and M. A. El-Hashash, “Synthesis, DFT Study, Molecular Docking and Insecticidal Evaluation of Some Pyrazole-Based Tetrahydropyrimidine Derivatives,” Synthetic Communications. 50, no. 8 (2020): 1159–75.
  • Y. Nagahara, and K. Nagahara, “Relationship between Structure and Antiproliferative Activity of Novel 5-Amino-4-Cyanopyrazole-1-Formaldehydehydrazono Derivatives on HL-60RG Human Leukemia Cells,” Anticancer Research 37, no. 11 (2017): 6329–33.
  • H. Raju, S. Chandrappa, D. S. Prasanna, H. Ananda, T. S. Nagamani, S. M. Byregowda, and K. S. Rangappa, “Synthesis, Characterization and in-Vitro Antiproliferative Effects of Novel 5-Amino Pyrazole Derivatives against Breast Cancer Cell Lines,” Recent Patents on anti-Cancer Drug Discovery 6, no. 2 (2011): 186–95.
  • P. Ravula, H. B. Vamaraju, M. Paturi, and J. N. Chandra, “Design, Synthesis, in Silico and Antiproliferative Evaluation of Novel Pyrazole Derivatives as VEGFR-2 Inhibitors,” Archiv Der Pharmazie 351, no. 1 (2018) : 1700234-235.
  • S. A. Rizk, G. A. Elsayed, and M. A. El-Hashash, “One-Pot Synthesis, Spectroscopic Characterization and DFT Study of Novel 8-Azacoumarin Derivatives as Eco-Friendly Insecticidal Agents,” Journal of the Iranian Chemical Society 15, no. 9 (2018): 2093–105.
  • M. A. El-Hashash, S. A. Rizk, F. A. El-Bassiouny, D. B. Guirguis, S. M. Khairy, and L. A. Guirguis, “Facile Synthesis and Structural Characterization of Some Phthalazine-1(2H)-One Derivatives as Antimicrobial Nucleosides and Reactive Dye,” Egyptian Journal of Chemistry. 60, no. 3 (2017): 407.
  • (a) Azab, M.E.; Rizk, S.A.; Mahmoud, N.F. “ Facile Synthesis, Characterization and Antimicrobial Evaluation of Novel Heterocycles, Schiff Bases, and N-nucleosides Bearing Phthalazine Moiety.” Chemical and Pharmaceutical Bulletin 2016, 64(5), 439. (b) 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 Advances 2020, 10(49), 29475.
  • E. A. Ghareeb, N. F. H. Mahmoud, E. A. El-Bordany, and E. A. E. El-Helw, “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,” Bioorganic Chemistry 112, (2021): 104945.
  • E. A. E. El-Helw, A. R. I. Morsy, and A. I. Hashem, “Evaluation of Some New Heterocycles Bearing 2-Oxoquinolyl Moiety as Immunomodulator against Highly Pathogenic Avian Influenza Virus (H5N8),” Journal of Heterocyclic Chemistry 58, no. 4 (2021): 1003–14.
  • A. A. El-Badawy, A. S. Elgubbi, and E. A. E. El-Helw, “Acryloyl Isothiocyanate Skeleton as a Precursor for Synthesis of Some Novel Pyrimidine, Triazole, Triazepine, Thiadiazolopyrimidine and Acylthiourea Derivatives as Antioxidant Agents,” Journal of Sulfur Chemistry 42, no. 3 (2021): 295–307.
  • E. A. E. El-Helw, and A. I. Hashem, “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,” Synthetic Communications 50, no. 7 (2020): 1046–55.
  • (a) M.S. Salem; E.A.E. El-Helw; H.A.Y. Derbala, “Development of Chromone-Pyrazole-Based Anticancer Agents,” Russian Journal of Bioorganic Chemistry 46, no. 1 (2020): 77. (b) A.M. El-Naggar; S.K. Ramadan, “Efficient Synthesis of Some Pyrimidine and Thiazolidine Derivatives Bearing Quinoline Scaffold under Microwave Irradiation,” Synthetic Communications 50, no. 14 (2020): 2188.
  • E. A. E. El-Helw, H. A. Sallam, and A. S. Elgubbi, “Antioxidant Activity of Some N-Heterocycles Derived from 2-(1-(2-Oxo-2H-Chromen-3-yl)Ethylidene) Hydrazinecarbothioamide,” Synthetic Communications 49, no. 20 (2019): 2651–61.
  • M. A. El-Helw, H. A. Derbala, M. M. El-Shahawi, M. S. Salem, and M. M. Ali, “Synthesis and in Vitro Antitumor Activity of Novel Chromenones Bearing Benzothiazole Moiety,” Russian Journal of Bioorganic Chemistry 45, no. 1 (2019): 42.
  • M. K. Bratenko, V. A. Chornous, and M. V. Vovk, “Functionally Substituted 3-Heterylpyrazoles: XI. 3-[3-Aryl(Heteryl)Pyrazol-4-yl]Propenoic and Propanoic Acids,” Russian Journal of Organic Chemistry 38, no. 8 (2002): 1171–7.
  • F. El-Taib Heakal, S. A. Rizk, and A. E. Elkholy, “Characterization of Newly Synthesized Pyrimidine Derivatives for Corrosion Inhibition as Inferred from Computational Chemical Analysis,” Journal of Molecular Structure 1152, (2018): 328–36.
  • L. E. Chirlian, and M. M. Francl, “Atomic Charges Derived from Electrostatic Potentials: A Detailed Study,” Journal of Computational Chemistry 8, no. 6 (1987): 894–905.
  • R. Dhingra, V. Margulets, S. R. Chowdhury, J. Thliveris, D. Jassal, P. Fernyhough, G. W. Dorn, and L. A. Kirshenbaum, “Kirshenbaum Bnip3 Mediates Doxorubicin-Induced Cardiac Myocyte Necrosis and Mortality through Changes in Mitochondrial Signaling,” Proceedings of the National Academy of Sciences of the United States of America 111, no. 51 (2014): E5537–E5544.
  • A. E. Elkholy, S. A. Rizk, and A. M. Rashad, “Enhancing Lubricating Oil Properties Using Novel Quinazolinone Derivatives: DFT Study and Molecular Dynamics Simulation,” Journal of Molecular Structure 1175, (2019): 788–96.
  • B. Kalyanaraman, “Teaching the Basics of the Mechanism of Doxorubicin-Induced Cardiotoxicity: Have we Been Barking up the Wrong Tree?,” Redox Biology 29, (2020): 101394.
  • X. Fang, H. Wang, D. Han, E. Xie, X. Yang, J. Wei, S. Gu, F. Gao, N. Zhu, X. Yin, et al. “Erroptosis as a Target for Protection against Cardiomyopathy,” Proceedings of the National Academy of Sciences of the United States of America 116, no. 7 (2019): 2672–80.
  • S. A. Rizk, M. A. El-Hashash, A. A. Youssef, and A. T. Elgendy, “A Green Microwave Method for Synthesizing a More Stable Phthalazin-1-ol Isomer as a Good Anticancer Reagent Using Chemical Plasma Organic Reactions,”Heliyon 7, no. 3 (2021): e06220.
  • S. K. Ramadan, and S. A. Rizk, “Synthesis, Density Functional Theory, and Cytotoxic Activity of Some Heterocyclic Systems Derived from 3‑(3‑(1,3‑Diphenyl‑1H‑Pyrazol‑4‑yl) Acryloyl)‑2H‑Chromen‑2‑One,” Journal of the Iranian Chemical Society. (2021) (in press). doi:10.1007/s13738-021-02298-6
  • T. Mosmann, “Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays,” Journal of Immunological Methods 65, no. 1-2 (1983): 55–63.
  • F. Denizot, and R. Lang, “Rapid Colorimetric Assay for Cell Growth and Survival. Modifications to the Tetrazolium Dye Procedure Giving Improved Sensitivity and Reliability,” Journal of Immunological Methods 89, no. 2 (1986): 271–7.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.