Synthesis, Cytotoxicity Evaluation and Molecular Docking Study of  N -Phenylpyrazoline Derivatives

Artania Adnin Tri Suma; Tutik Dwi Wahyuningsih; Mustofa Mustofa

doi:10.22146/ijc.45777

Synthesis, Cytotoxicity Evaluation and Molecular Docking Study of N-Phenylpyrazoline Derivatives

https://doi.org/10.22146/ijc.45777

Artania Adnin Tri Suma⁽¹⁾, Tutik Dwi Wahyuningsih^(2*), Mustofa Mustofa⁽³⁾

(1) Laboratory of Organic Chemistry, Department of Chemistry, Universitas Gadjah Mada
(2) Laboratory of Organic Chemistry, Department of Chemistry, Universitas Gadjah Mada
(3) Department of Pharmacology and Therapy, Faculty of Medicine, Universitas Gadjah Mada,
(*) Corresponding Author

Abstract

The synthesis of N-phenylpyrazolines 1-5 was performed by the cyclocondensation of phenylhydrazine and appropriate chalcones that have been synthesized from our previous work. All of the compounds were elucidated for their structure using GC-MS, FTIR, ¹H, and ¹³C-NMR spectrometers. Their anticancer activity was evaluated against breast cancer cell line (T47D) and colorectal cancer cell line (WiDr). Compound 4 (4-(3-(4-chlorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl)-2-methoxyphenol) was found to be the most potent compound with IC₅₀ value of 13.11 µg/mL in T47D cell line and 3.29 µg/mL in WiDr cell line. Docking study was conducted to evaluate the interaction between all compounds and EGFR receptor on cancer cells. Among the tested compounds, compound 4 is the only compound that has interaction with MET769 residue through hydrogen bonding due to the presence of hydroxyl group on its structure. Our findings suggest that the synthesized N-phenylpyrazolines in this study have a promising anticancer activity.

Keywords

N-phenylpyrazoline, anticancer, cytotoxic activity, molecular docking

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DOI: https://doi.org/10.22146/ijc.45777