Synthesis, Characterization, Cytotoxicity Study and Docking Studies of New Fused-pyrazoline Derivatives derived from Bis-Chalcones Against Breast Cancer cells

Alidmat, Mohammad Murwih; Ning, Tan Zhi; Khairuddean, Melati; Shayazi, Nurul Hayati; Nik Mohammad Kamal, Nik Nur Syazni; Muhammad, Musthahimah

doi:10.21608/ejchem.2021.73796.3648

Synthesis, Characterization, Cytotoxicity Study and Docking Studies of New Fused-pyrazoline Derivatives derived from Bis-Chalcones Against Breast Cancer cells

Document Type : Original Article

Authors

¹ School of chemical science Universiti Sains Malaysia

² School of Chemical Sciences, University Sains Malaysia, 11800 Penang, Malaysia

³ Advanced Medical and Dental Institute, Universiti Sains Malaysia, 13200 Kepala Batas, Penang, Malaysia

10.21608/ejchem.2021.73796.3648

Abstract

Breast cancer is one of the prevalent diseases that kill millions of women worldwide. The development of resistance and side effects of chemotherapy drugs is a common obstacle in the treatment of breast cancer. Recently, the focus of drug discovery has increased toward a valuable structure known as chalcones due to their extensive bioactivity in cancer treatment. In this study, 6 chalcones and 4 fused-pyrazoline derivatives have been synthesized (1-6) using the Claisen-Schmidt condensation technique for cyclopentanone and cyclohexanone with different aromatic aldehydes at room temperature. Chalcones 2-3 and 5-6 were used in cyclo-condensation reaction with thiosemicarbazide to form new fused pyrazoline derivatives. All the synthesized chalcones and fused pyrazoline were characterized using ATR-FTIR, H-NMR and 13C-NMR (1D ). The cytotoxic activity of these new chalcone compounds was investigated against breast cancer cell lines (MCF-7) and normal breast cell lines (MCF-10A). The results showed that compounds 1 and 10 exhibited significant antiproliferative effects against MCF-7 with IC50 values of 8 µM and 8.5 µM when exposed for 48 hours compared with the reference anticancer drug, tamoxifen. Molecular docking analysis showed that compounds 1 and 10 entered the pocket of ERα and interaction with the amino acids in high affinity of binding as tamoxifen.

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