Research Articles

2019  |  Vol: 5(5)  |  Issue: 5(September- October)  |  https://doi.org/10.31024/ajpp.2019.5.5.22
Synthesis, characterization, molecular docking and evaluation of anticancer activity of 2- pyrazoline derivatives

Benupani Sahu1, Subhasish Mondal1, Sudipa Mondal2, Chiranjit Patra2, Tanushree Singha1, Tapan Kumar Maity1*

1Division of Pharmaceutical Chemistry, Department of Pharmaceutical Technology, Jadavpur University, Kolkata – 700032, India

2Department of Chemistry, Jadavpur University, Kolkata – 700032, India

*Address for Corresponding Author

Professor (Dr.) Tapan Kumar Maity

Department of Pharmaceutical Technology, Jadavpur University, Kolkata-700032, India

Abstract

Objectives: 5-Substituted aryl-2-pyrazoline derivatives (5a-f) were synthesized by Claisen Schmit reaction method for their molecular docking and evaluation of their anticancer activity. Materials and Methods: 2-pyrazoline derivatives (5a-f) were characterized by spectroscopic (FTIR, 1H NMR, 13C NMR and Mass) analysis after synthesis. All compounds were screened for their in vivo anticancer activity using Ehrlich ascites carcinoma (EAC) cells and their in vitro anticancer activity also performed against Human breast adenocarcinoma cell line (MCF-7). Molecular docking study was performed using the CDOCKER protocol in Discovery Studio 3.5. Results:  In the in vivo assay, 1-(2,4-dinitrophenyl)-5-(2-chlorophenyl)-3-(4-methoxyphenyl)-2-pyrazoline (5b) and 1-(2,4-dinitrophenyl)-5-(3-nitrophenyl)-3-(4-methoxyphenyl)-2-pyrazoline (5f) exhibited significant anticancer activity as compared to the standard drug 5-FU.  But in vitro assay, compound 1-(2, 4-dinitrophenyl)-5-(4-chlorophenyl)-3-(4-methoxyphenyl)-2-pyrazoline (5c) and 1-(2,4-dinitrophenyl)-5-(4-N,N dimethylaminophenyl)-3-(4-methoxyphenyl)-2 pyrazoline (5e) were emerged as more potent inhibitor of MCF-7 with IC50 2.42±0.26 mg/l and 2.75±0.33 mg/l respectively when compared with standard drug 5-Fluorouracil (5-FU) with IC50 was 9.84±2.57 mg/l).. Docking simulation of these compounds with epidermal growth factor receptor (EGFR) protein was used to determine the best pose binding mode and supportive mechanism of action. Conclusions: Hence compound 1-(2, 4-dinitrophenyl)-5-(4- chlorophenyl)-3-(4-methoxyphenyl)-2-pyrazoline (5c) and compound 1-(2, 4-dinitrophenyl)-5-(4-N, N-dimetyl amino phenyl)-3-(4-methoxyphenyl)-2-pyrazoline (5e) could be considered as bioactive molecules for future development and research and hope to get more target specific, less toxic and potent anticancer activity.

Keywords: 2-Pyrazoline, MCF-7, EAC cells, MTT assay, Molecular docking, EGFR, 5-Fluorouracil

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