Synthesis, characterization, molecular docking and in vitro anticancer activity of 3-(4-methoxyphenyl)-5-substituted phenyl-2-pyrazoline-1- carbothioamide

Benupani Sahu; Rajapandi R; Avik Maji; Abhik Paul; Tanushree Singha; Tapan Kumar Maity

Benupani Sahu ⁽¹⁾ , Rajapandi R ⁽²⁾ , Avik Maji ⁽³⁾ , Abhik Paul ⁽⁴⁾ , Tanushree Singha ⁽⁵⁾ , Tapan Kumar Maity ⁽⁶⁾

(1) Division of Pharmaceutical Chemistry, Department of Pharmaceutical Technology, Jadavpur University, Kolkata – 700032, West Bengal, India, India ,

(2) Department of Pharmaceutical Chemistry, Arulmigu Kalasalingam College of Pharmacy, Krishnan Koil – 626126, Tamilnadu, India, India ,

(3) Division of Pharmaceutical Chemistry, Department of Pharmaceutical Technology, Jadavpur University, Kolkata – 700032, West Bengal, India, India ,

(4) Division of Pharmaceutical Chemistry, Department of Pharmaceutical Technology, Jadavpur University, Kolkata – 700032, West Bengal, India, India ,

(5) Division of Pharmaceutical Chemistry, Department of Pharmaceutical Technology, Jadavpur University, Kolkata – 700032, West Bengal, India, India ,

(6) Division of Pharmaceutical Chemistry, Department of Pharmaceutical Technology, Jadavpur University, Kolkata – 700032, West Bengal, India, India

Issue
Vol. 12 No. 2 (2021): Volume 12 Issue 2

Keywords:

Anticancer, Molecular docking, Pyrazoline, SRB Assay and Molegro Virtual Docker

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Abstract

In the present study, eight numbers of new 3- (4-methoxy phenyl)-5-substituted phenyl-2-pyrazoline-1-carbothioamide (5a-h) have been synthesized from 1- (4-methoxy phenyl)-3- (substituted phenyl)-prop-2-en-1-one (3a-h) and structurally characterized by using FT-IR, 1H NMR, 13C NMR, Mass and Elemental analysis. The synthesized molecules were biologically evaluated for their in vitro anticancer activity against human breast adenocarcinoma (MCF-7), liver cancer (Hep-G2) and leukaemia cancer (K-562) cell line using Sulforhodamine B (SRB) bioassay technique. From the all-synthesized compounds 5a, 5c, 5d, and 5e exhibited potent anticancer activity (GI50= <10µg/ml) as compared to the controlled drug 5-Fluorouracil (5-FU) (GI50=44.5µg/ml) and Adriamycin (ADR) (GI50= <10µg/ml) on MCF-7 cell lines. Besides this, all the synthesized compounds have exhibited moderate activity against human liver cancer (Hep-G2) and leukaemia cancer (K-562) cell lines. In addition, molecular docking studies were also explored in order to study the probable binding specificity into the active site of Epidermal Growth Factor Receptor tyrosine kinase (EGFR) (PDB ID: 1M17) using Molegro Virtual Docker Evaluation 2013 6.0.1 (MVD). Based on the molecular docking result, it was found that compound 5a exhibited the best interaction with the above target (i.e., EGFR) by interacting with specific amino acid residues such as: Thr 766, Gin 767, Thr 830, Cys 575, Ala 719 and Met 769.

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