European Journal of Chemistry 2017, 8(4), 391-399 | doi: https://doi.org/10.5155/eurjchem.8.4.391-399.1652 | Get rights and content






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Synthesis and biological evaluation of phthalimide dithiocarbamate and dithioate derivatives as anti-proliferative and anti-angiogenic agents-I


Magdy Zahran (1) , Hussein Agwa (2,*) , Amany Osman (3) , Sherif Hammad (4) , Bishoy El-Aarag (5) , Nasser Ismail (6) , Tarek Salem (7) , Amira Gamal-Eldeen (8)

(1) Chemistry Department, Faculty of Science, Menoufia University, Shebin El-Koom, 32511, Egypt
(2) Chemistry Department, Faculty of Science, Menoufia University, Shebin El-Koom, 32511, Egypt
(3) Chemistry Department, Faculty of Science, Menoufia University, Shebin El-Koom, 32511, Egypt
(4) Research and Development Department, Pharco B International Company for Pharmaceutical Industries, Borg El-Arab, Alexandria, 21934, Egypt
(5) Biochemistry Division, Chemistry Department, Faculty of Science, Menoufia University, Shebin El-Koom, 32511, Egypt
(6) Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ain-Shams University, Cairo, 11599, Egypt
(7) Molecular Biology Department, Genetic Engineering and Biotechnology Research Institute (GEBRI), Sadat City University, Sadat City, 32897, Egypt
(8) Cancer Biology and Genetics Laboratory, Centre of Excellence for Advanced Sciences, National Research Centre, Dokki, Cairo, 11599, Egypt
(*) Corresponding Author

Received: 15 Sep 2017 | Revised: 23 Oct 2017 | Accepted: 25 Oct 2017 | Published: 31 Dec 2017 | Issue Date: December 2017

Abstract


A facile synthesis of new phthalimide dithiocarbamate and dithioate analogs 8a-j, 9a-e and 9g-j were achieved by the reaction of N-chloromethyl and N-bromoethylphthalimide with carbon disulfide (CS2) and various amines. The structures of the synthesized analogs were elucidated by spectroscopic methods, including IR, 1H NMR and 13C NMR, and ESI-HRMS techniques. The antiproliferative activity of the newly synthesized compounds was also evaluated against various human cancer cell lines. The compound 9e and 9i exhibited the highest activity against human breast adenocarcinoma MCF-7 and hepatocellular carcinoma HepG2 cells. Compound 8f showed better antiproliferative effect against colon carcinoma HCT-116 and cervical carcinoma HeLa compared to thalidomide. The binding affinity to vascular endothelial growth factor receptor (VEGFR) of some compounds was assessed in addition to molecular docking study. Compounds 9e and 9i showed high docking score values and they significantly declined the concentration of VEGFR.


Keywords


Cytotoxicity; Phthalimide; Thalidomide; Dithiocarbamate; Antitumor activity; Molecular Docking

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DOI: 10.5155/eurjchem.8.4.391-399.1652

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Funding information


Science and Technology Development Fund (STDF) through Project No. 3627 (Egyptian fund); Prof. Erik Pedersen, Department of Physics, Chemistry and Pharmacy, Nucleic Acid Center, University of Southern Denmark, Odense, Denmark.

Citations

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[1]. El-Saied, El-Aarag, Salem, Said, Khalifa, El-Seedi
Synthesis, Characterization, and In Vivo Anti-Cancer Activity of New Metal Complexes Derived from Isatin-N(4)antipyrinethiosemicarbazone Ligand Against Ehrlich Ascites Carcinoma Cells
Molecules  24(18), 3313, 2019
DOI: 10.3390/molecules24183313
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[2]. Ismail M. M. Othman, Mohamed A. M. Gad-Elkareem, Mohamed El-Naggar, Eman S. Nossier, Abd El-Galil E. Amr
Novel phthalimide based analogues: design, synthesis, biological evaluation, and molecular docking studies
Journal of Enzyme Inhibition and Medicinal Chemistry  34(1), 1259, 2019
DOI: 10.1080/14756366.2019.1637861
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How to cite


Zahran, M.; Agwa, H.; Osman, A.; Hammad, S.; El-Aarag, B.; Ismail, N.; Salem, T.; Gamal-Eldeen, A. Eur. J. Chem. 2017, 8(4), 391-399. doi:10.5155/eurjchem.8.4.391-399.1652
Zahran, M.; Agwa, H.; Osman, A.; Hammad, S.; El-Aarag, B.; Ismail, N.; Salem, T.; Gamal-Eldeen, A. Synthesis and biological evaluation of phthalimide dithiocarbamate and dithioate derivatives as anti-proliferative and anti-angiogenic agents-I. Eur. J. Chem. 2017, 8(4), 391-399. doi:10.5155/eurjchem.8.4.391-399.1652
Zahran, M., Agwa, H., Osman, A., Hammad, S., El-Aarag, B., Ismail, N., Salem, T., & Gamal-Eldeen, A. (2017). Synthesis and biological evaluation of phthalimide dithiocarbamate and dithioate derivatives as anti-proliferative and anti-angiogenic agents-I. European Journal of Chemistry, 8(4), 391-399. doi:10.5155/eurjchem.8.4.391-399.1652
Zahran, Magdy, Hussein Agwa, Amany Osman, Sherif Hammad, Bishoy El-Aarag, Nasser Ismail, Tarek Salem, & Amira Gamal-Eldeen. "Synthesis and biological evaluation of phthalimide dithiocarbamate and dithioate derivatives as anti-proliferative and anti-angiogenic agents-I." European Journal of Chemistry [Online], 8.4 (2017): 391-399. Web. 9 Aug. 2020
Zahran, Magdy, Agwa, Hussein, Osman, Amany, Hammad, Sherif, El-Aarag, Bishoy, Ismail, Nasser, Salem, Tarek, AND Gamal-Eldeen, Amira. "Synthesis and biological evaluation of phthalimide dithiocarbamate and dithioate derivatives as anti-proliferative and anti-angiogenic agents-I" European Journal of Chemistry [Online], Volume 8 Number 4 (31 December 2017)

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