Synthesis and biological evaluation of 3-(2,4-dichlorophenoxymethyl)-1-phenyl-1 H -pyrazole derivatives as potential ant
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ORIGINAL PAPER
Synthesis and biological evaluation of 3‑(2,4‑dichlorophenoxymethyl)‑1‑phenyl‑1H‑pyrazole derivatives as potential antitumor agents Mohamed F. El Shehry1 · Samir Y. Abbas2 · Amel M. Farrag3 · Sawsan A. Fouad4 · Yousry A. Ammar5 Received: 22 March 2020 / Accepted: 4 May 2020 © Iranian Chemical Society 2020
Abstract Series of novel 3-(2,4-dichlorophenoxymethyl)-1-phenyl-1H-pyrazole derivatives with various substituents at positions 4 and 5 were synthesized. Antitumor activity of all the synthesized compounds was evaluated by using SRB assay on four cell lines: lung carcinoma (A549), human hepatocellular carcinoma (HepG2), colon carcinoma (HCT116) and mammary gland breast cancer (MCF-7) cell lines. Some of the synthesized compounds showed promising activity in comparison with doxorubicin against lung carcinoma cell lines. Incorporating arylidene moiety at position-4 in pyrazole ring improved and displayed strong effect on the cytotoxic activity. Compound 9c incorporating 4-chlorophenyl moiety was the most potent toward all tested cell lines. Keywords Pyrazoles · Schiff’s bases · Hydrazones · Vinyl derivative · Antitumor agents
Introduction Pyrazole is one of the important moieties of heterocyclic compounds. The first pyrazole was synthesized by Knorr in 1883, which led to discovery of antipyrine and its derivatives. Great attention has been focused on pyrazole derivatives as potent anti-inflammatory, analgesic, antipyretic Electronic supplementary material The online version of this article (https://doi.org/10.1007/s13738-020-01951-w) contains supplementary material, which is available to authorized users. * Samir Y. Abbas [email protected] * Yousry A. Ammar [email protected] 1
Pesticide Chemistry Department, National Research Centre, Cairo 12622, Egypt
2
Organometallic and Organometalloid Chemistry Department, National Research Centre, Cairo, Egypt
3
Pharmaceutical Chemistry Department, Faculty of Pharmacy (Girls), Al-Azher University, Nasr City, Cairo, Egypt
4
Chemistry Department, Faculty of Science, Al-Azhar University (Girls), Cairo, Egypt
5
Chemistry Department, Faculty of Science, Al-Azhar University, Cairo, Egypt
agents [1–3]. Pyrazoles have important roles among antitumor agents; they play as good inhibitor against EGFR, BRAFV600E, ROS receptor tyrosine kinase, telomerase, and Aurora-A kinase. There are many of drugs incorporating pyrazole moiety such as antipyrine, celecoxib, novalgine, phenylbutazone, apixaban, ramifenazone, rimonabant, fipronil, pyrazofurin [4–6]. Moreover, many of pyrazole derivatives have another broad spectra of biological activities, such as antimicrobial [7] antiviral [8] and herbicidal activities [9]. Dichlorophenoxy moiety showed systemic herbicide. (2,4-Dichlorophenoxy) acetic acid (2,4-D) are used in the control of broadleaf weeds. During the last six decades, many research were carried out on (2,4-dichlorophenoxy) acetic acid [10]. Schiff’s base derivatives are interesting in medicinal chemistry due to their diverse biological pr
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