Novel Synthesis, Docking studies and Antitumor Evaluation of Pyrazolo- and Pyrazolo Aminophosphonate Derivatives Derived from N-Heterocyclic Amines
Khidre, M., Abdelaleem, F., Abu Bakr, S., Awad, H., Sabry, E. (2022). Novel Synthesis, Docking studies and Antitumor Evaluation of Pyrazolo- and Pyrazolo Aminophosphonate Derivatives Derived from N-Heterocyclic Amines. EKB Journal Management System, 65(9), 657-672. doi: 10.21608/ejchem.2022.125116.5562
Maha Khidre; Fatma Abdelaleem; Sherifa Abu Bakr; Hanem Awad; Eman Sabry. "Novel Synthesis, Docking studies and Antitumor Evaluation of Pyrazolo- and Pyrazolo Aminophosphonate Derivatives Derived from N-Heterocyclic Amines". EKB Journal Management System, 65, 9, 2022, 657-672. doi: 10.21608/ejchem.2022.125116.5562
Khidre, M., Abdelaleem, F., Abu Bakr, S., Awad, H., Sabry, E. (2022). 'Novel Synthesis, Docking studies and Antitumor Evaluation of Pyrazolo- and Pyrazolo Aminophosphonate Derivatives Derived from N-Heterocyclic Amines', EKB Journal Management System, 65(9), pp. 657-672. doi: 10.21608/ejchem.2022.125116.5562
Khidre, M., Abdelaleem, F., Abu Bakr, S., Awad, H., Sabry, E. Novel Synthesis, Docking studies and Antitumor Evaluation of Pyrazolo- and Pyrazolo Aminophosphonate Derivatives Derived from N-Heterocyclic Amines. EKB Journal Management System, 2022; 65(9): 657-672. doi: 10.21608/ejchem.2022.125116.5562

Novel Synthesis, Docking studies and Antitumor Evaluation of Pyrazolo- and Pyrazolo Aminophosphonate Derivatives Derived from N-Heterocyclic Amines

Egyptian Journal of Chemistry
Article 60, Volume 65, Issue 9, September 2022, Page 657-672  XML PDF (831.9 K)
Document Type: Original Article
DOI: 10.21608/ejchem.2022.125116.5562
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Authors
Maha Khidre1; Fatma Abdelaleemorcid 2; Sherifa Abu Bakr2; Hanem Awadorcid 3; Eman Sabry email orcid 4
1Pesticide Chemistry Department, National Research Centre (NRC), Giza, Egypt
2Department of Chemistry of Natural and Microbial Products, Institute of Pharmaceutical and Drug Industries, National Research Centre,
3Department of Tanning Materials and Leather Technology, National Research Centre
4Chemical Industries Research Division, National Research Centre, Giza, Egypt.
Abstract
Amino thiophene carbonitrile 1 reacted with chloropyrazole carbaldehyde 2a,b to afford Schiff bases 3a,b in good yield via condensation reaction. Compounds 3a,b reacted with different primary and secondary amines to afford pyrazolo derivatives 4-10. Also, one-pot Kabachnic-Fields reaction invloved the synthesis of α-aminophosphonates by condensation of pyrazole-5-carbaldehyde derivatives, N-heterocyclic amines and trialkylphosphites in moderate yields. α-Aminophosphonates were also produced in high yields (75%) by reacting Schiff bases directly with dialkylphosphites. In addition, hexaalkyl triamidophosphites were applied to the Schiff bases in THF to afford the amino derivatives in high yields. Molecular modelling investigations were studied to explore the possible binding interactions which revealed that compounds 8, 7, and 3b were the most promising candidates comparing with Doxorubicin. Antitumor activity of new compounds was tested on three cell lines of liver (HepG2), breast (MCF7) carcinoma cell lines and HCT-116 cancer cells together with human healthy cell line (BJ-1) using the MTT assay.
Keywords
α -Aminophosphonate; Antitumor activity; Docking studies; Kabachnik– Fields; Pyrazole-5-carbaldehyde; Tetrahydrobenzo[b]thiophene
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