Synthesis, characterization, and cytotoxic activity of some new 1,3,4-trisubstituted pyrazoles against diverse tumor cell lines

Synthesis, characterization, and cytotoxic activity of some new 1,3,4-trisubstituted pyrazoles... New derivatives of 1,3,4-trisubstituted pyrazole have been synthesized via different reaction routs starting with the chalcone (E)-3-[3-(4-bromophenyl)-1-ethyl-1H-pyrazol-4-yl]-1-(4-chlorophenyl)prop-2-en-1-one and dicarbonitrile 2-[[3- (4-bromophenyl)-1-ethyl-1H-pyrazol-4-yl]methylene]malononitrile derived from 3-(4-bromophenyl)-1H-pyrazole-4-carb- aldehyde, and the in-vitro anti-cancer activity has been tested against various human cancer cell lines, namely: hepato- cellular carcinoma HepG2, breast cancer MCF7, lung carcinoma A549, prostatic cancer PC3, and colon carcinoma HCT116. Some of the tested analogs exhibited significant activity on the target cell lines, and compound 4-[3-(4-bro- mophenyl)-1-ethyl-1H-pyrazol-4-yl]-1,2-dihydro-2-oxo-6-(pyridin-2-yl)pyridine-3-carbonitrile was not only the most potent among the tested compounds with IC = 9.130, 11.957, 9.130, 29.130, and 8.913 lM, compared with the reference standard doxorubicin (IC = 34.242, 20.851, 5.928, 38.024, 7.174 lM) on HepG2, MCF7, A549, PC3, and HCT116 cell lines, respectively, but also displayed no cytotoxic activity on the BJ-1 fibroblast normal human cell line. Objectively, the newly synthesized analogs can serve as a brick for the development of potent anti-cancer agents. Graphical abstract IC 1.1 0.9 0.8 0.7 0.6 0.5 0.4 0.3 0.2 0.1 0 102030405060708090 100 Keywords Trisubstituted pyrazole  Claisen–Schmidt  Knoevenagel  Anti-cancer Introduction Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00706-018-2153-7) contains supplementary Cancer is a major worldwide health problem with material, which is available http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Monatshefte für Chemie - Chemical Monthly Springer Journals

Synthesis, characterization, and cytotoxic activity of some new 1,3,4-trisubstituted pyrazoles against diverse tumor cell lines

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Publisher
Springer Vienna
Copyright
Copyright © 2018 by Springer-Verlag GmbH Austria, part of Springer Nature
Subject
Chemistry; Chemistry/Food Science, general; Organic Chemistry; Inorganic Chemistry; Analytical Chemistry; Physical Chemistry; Theoretical and Computational Chemistry
ISSN
0026-9247
eISSN
1434-4475
D.O.I.
10.1007/s00706-018-2153-7
Publisher site
See Article on Publisher Site

Abstract

New derivatives of 1,3,4-trisubstituted pyrazole have been synthesized via different reaction routs starting with the chalcone (E)-3-[3-(4-bromophenyl)-1-ethyl-1H-pyrazol-4-yl]-1-(4-chlorophenyl)prop-2-en-1-one and dicarbonitrile 2-[[3- (4-bromophenyl)-1-ethyl-1H-pyrazol-4-yl]methylene]malononitrile derived from 3-(4-bromophenyl)-1H-pyrazole-4-carb- aldehyde, and the in-vitro anti-cancer activity has been tested against various human cancer cell lines, namely: hepato- cellular carcinoma HepG2, breast cancer MCF7, lung carcinoma A549, prostatic cancer PC3, and colon carcinoma HCT116. Some of the tested analogs exhibited significant activity on the target cell lines, and compound 4-[3-(4-bro- mophenyl)-1-ethyl-1H-pyrazol-4-yl]-1,2-dihydro-2-oxo-6-(pyridin-2-yl)pyridine-3-carbonitrile was not only the most potent among the tested compounds with IC = 9.130, 11.957, 9.130, 29.130, and 8.913 lM, compared with the reference standard doxorubicin (IC = 34.242, 20.851, 5.928, 38.024, 7.174 lM) on HepG2, MCF7, A549, PC3, and HCT116 cell lines, respectively, but also displayed no cytotoxic activity on the BJ-1 fibroblast normal human cell line. Objectively, the newly synthesized analogs can serve as a brick for the development of potent anti-cancer agents. Graphical abstract IC 1.1 0.9 0.8 0.7 0.6 0.5 0.4 0.3 0.2 0.1 0 102030405060708090 100 Keywords Trisubstituted pyrazole  Claisen–Schmidt  Knoevenagel  Anti-cancer Introduction Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00706-018-2153-7) contains supplementary Cancer is a major worldwide health problem with material, which is available

Journal

Monatshefte für Chemie - Chemical MonthlySpringer Journals

Published: Feb 17, 2018

References

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