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 |
Pyrazole, Thiazole, Antiproliferative, Cell Cycle Analysis, Annexin-V, Topoisomerase II
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APA Style
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
ACS Style
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
AMA Style
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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Download@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}
}
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 PY - 2019 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 SP - 55 EP - 70 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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