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In vitro Anti Leukemia Cancer Activity of Some Novel Pyrazole Derivatives and Pyrazoles Containing Thiazole Moiety

Received: 30 June 2019     Accepted: 1 August 2019     Published: 14 August 2019
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Abstract

The design and syntheses of several novel pyrazole derivatives (2, 5, 6 and 7) and pyrazole derivatives (3 and 4) containing thiazole moiety via by ethyl β-(p-chlorophenyl)–α-cyanoacrylate (1) and thiosemicarbazide as starting materials. Pyrazole derivatives (3 and 4) containing thiazole moiety were synthesized via cyclization of pyrazole derivative (2) with bromomethyl arylketones, to give compound 3, followed by acetylation. N- (3- methoxy-2-hydroxybenzal) -3- (p -chlorophenyl)-4- cyano-5-oxopyrazol-1-thiocarboxamide (6) was synthesized via reaction of compound 2 with 3-methoxy-2-hydroxybenzaldehyde. Structures of all compounds were confirmed by elemental analysis, FT-IR, 1H-NMR, 13C-NMR and mass spectrometry. The cytotoxic activity of all the synthetic compounds were evaluated against Leukemia HL-60 compared with Doxorubicicn. The cytotoxic activity was checked in vitro for the recently prepared compounds by using the MTT assay. Compounds 4, 6 and 9 were the most active against Leukemia HL-60. The IC50 values of them were less than 5 µM in the range of 1.35-4.78 µM. In addition, compounds 3 and 5 showed less antiproliferative activity against Leukemia HL-60 cells with IC50 values in the range 5.39-8.82 µM. Compound 6 was the most potent cytotoxic activity. The studies biological activity includes cell cycle analysis, apoptosis detection assay and Topoisomerase II inhibition activity assay explained that compound 6 is a strong Topo II inhibitor.

Published in American Journal of Heterocyclic Chemistry (Volume 5, Issue 3)
DOI 10.11648/j.ajhc.20190503.12
Page(s) 55-70
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2019. Published by Science Publishing Group

Keywords

Pyrazole, Thiazole, Antiproliferative, Cell Cycle Analysis, Annexin-V, Topoisomerase II

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    Amal Mahmoud Youssef Moustafa. (2019). In vitro Anti Leukemia Cancer Activity of Some Novel Pyrazole Derivatives and Pyrazoles Containing Thiazole Moiety. American Journal of Heterocyclic Chemistry, 5(3), 55-70. https://doi.org/10.11648/j.ajhc.20190503.12

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    Amal Mahmoud Youssef Moustafa. In vitro Anti Leukemia Cancer Activity of Some Novel Pyrazole Derivatives and Pyrazoles Containing Thiazole Moiety. Am. J. Heterocycl. Chem. 2019, 5(3), 55-70. doi: 10.11648/j.ajhc.20190503.12

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    Amal Mahmoud Youssef Moustafa. In vitro Anti Leukemia Cancer Activity of Some Novel Pyrazole Derivatives and Pyrazoles Containing Thiazole Moiety. Am J Heterocycl Chem. 2019;5(3):55-70. doi: 10.11648/j.ajhc.20190503.12

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  • @article{10.11648/j.ajhc.20190503.12,
      author = {Amal Mahmoud Youssef Moustafa},
      title = {In vitro Anti Leukemia Cancer Activity of Some Novel Pyrazole Derivatives and Pyrazoles Containing Thiazole Moiety},
      journal = {American Journal of Heterocyclic Chemistry},
      volume = {5},
      number = {3},
      pages = {55-70},
      doi = {10.11648/j.ajhc.20190503.12},
      url = {https://doi.org/10.11648/j.ajhc.20190503.12},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20190503.12},
      abstract = {The design and syntheses of several novel pyrazole derivatives (2, 5, 6 and 7) and pyrazole derivatives (3 and 4) containing thiazole moiety via by ethyl β-(p-chlorophenyl)–α-cyanoacrylate (1) and thiosemicarbazide as starting materials. Pyrazole derivatives (3 and 4) containing thiazole moiety were synthesized via cyclization of pyrazole derivative (2) with bromomethyl arylketones, to give compound 3, followed by acetylation. N- (3- methoxy-2-hydroxybenzal) -3- (p -chlorophenyl)-4- cyano-5-oxopyrazol-1-thiocarboxamide (6) was synthesized via reaction of compound 2 with 3-methoxy-2-hydroxybenzaldehyde. Structures of all compounds were confirmed by elemental analysis, FT-IR, 1H-NMR, 13C-NMR and mass spectrometry. The cytotoxic activity of all the synthetic compounds were evaluated against Leukemia HL-60 compared with Doxorubicicn. The cytotoxic activity was checked in vitro for the recently prepared compounds by using the MTT assay. Compounds 4, 6 and 9 were the most active against Leukemia HL-60. The IC50 values of them were less than 5 µM in the range of 1.35-4.78 µM. In addition, compounds 3 and 5 showed less antiproliferative activity against Leukemia HL-60 cells with IC50 values in the range 5.39-8.82 µM. Compound 6 was the most potent cytotoxic activity. The studies biological activity includes cell cycle analysis, apoptosis detection assay and Topoisomerase II inhibition activity assay explained that compound 6 is a strong Topo II inhibitor.},
     year = {2019}
    }
    

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  • TY  - JOUR
    T1  - In vitro Anti Leukemia Cancer Activity of Some Novel Pyrazole Derivatives and Pyrazoles Containing Thiazole Moiety
    AU  - Amal Mahmoud Youssef Moustafa
    Y1  - 2019/08/14
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    N1  - https://doi.org/10.11648/j.ajhc.20190503.12
    DO  - 10.11648/j.ajhc.20190503.12
    T2  - American Journal of Heterocyclic Chemistry
    JF  - American Journal of Heterocyclic Chemistry
    JO  - American Journal of Heterocyclic Chemistry
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    PB  - Science Publishing Group
    SN  - 2575-5722
    UR  - https://doi.org/10.11648/j.ajhc.20190503.12
    AB  - The design and syntheses of several novel pyrazole derivatives (2, 5, 6 and 7) and pyrazole derivatives (3 and 4) containing thiazole moiety via by ethyl β-(p-chlorophenyl)–α-cyanoacrylate (1) and thiosemicarbazide as starting materials. Pyrazole derivatives (3 and 4) containing thiazole moiety were synthesized via cyclization of pyrazole derivative (2) with bromomethyl arylketones, to give compound 3, followed by acetylation. N- (3- methoxy-2-hydroxybenzal) -3- (p -chlorophenyl)-4- cyano-5-oxopyrazol-1-thiocarboxamide (6) was synthesized via reaction of compound 2 with 3-methoxy-2-hydroxybenzaldehyde. Structures of all compounds were confirmed by elemental analysis, FT-IR, 1H-NMR, 13C-NMR and mass spectrometry. The cytotoxic activity of all the synthetic compounds were evaluated against Leukemia HL-60 compared with Doxorubicicn. The cytotoxic activity was checked in vitro for the recently prepared compounds by using the MTT assay. Compounds 4, 6 and 9 were the most active against Leukemia HL-60. The IC50 values of them were less than 5 µM in the range of 1.35-4.78 µM. In addition, compounds 3 and 5 showed less antiproliferative activity against Leukemia HL-60 cells with IC50 values in the range 5.39-8.82 µM. Compound 6 was the most potent cytotoxic activity. The studies biological activity includes cell cycle analysis, apoptosis detection assay and Topoisomerase II inhibition activity assay explained that compound 6 is a strong Topo II inhibitor.
    VL  - 5
    IS  - 3
    ER  - 

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Author Information
  • Chemistry Department, Faculty of Science, Port Said University, Port Said, Egypt

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