New Fluorinated Chalcone and Pyrazolines Analogues: Synthesis, Docking and Molecular Dynamic Studies as Anticancer Agents

Jasril Jasril

Abstract


Some of chalcones and pyrazolines analogues are known to have a good potency as anticancer agents. In this work, a fluorinated chalcone and two pyrazolines were successfully synthesized under microwave irradiation. Molecular docking and molecular dynamic (MD) were performed to observe the potency of these compounds as anticancer against MCF7 cell line (i.e. breast cancer). Base on these methods, it indicates that hydrogen bonding, van der Waals and electrostatic interaction were assumed to be enhancing the biological activity of those compounds. Based on the result, compound 1 and compound 2 showed a good potential against MCF7 cell line and it can be used and chosen as the reference for the next stage in drug design, whereas compound 3 has another mode of action against MCF7 line.


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References


Widiandani T, Arifianti L, Siswandono. Docking, synthesis and cytotoxicity test on human breast cancer cell line (T47D) of N-(allylcarbamothoyl)benzamide. Int J Pharm Clin Res. 2016; 8:372-376.

O’Hagan D. Understanding organofluorine chemistry. An introduction to the C-F bond. Chem. Soc. Rev. 2008. 37: 308–319.

Aguilar JA, Morris GA, Kenwrigh AM. Pure shift 1H NMR, a robust method for revealing heteronuclear coupling in complex spectra. RSC Adv. 2014; 4: 8278-8282.

Purser S, Moore PR, Swallow S, Gouverneur V. Fluorine in medicinal chemistry. Chem. Soc. Rev. 2008; 37: 320–330.

Jasril J, Zamri A, Ikhtiarudin I, Teruna HY. 5-(4-fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-4,5- dihydro-1H-pyrazole. Molbank. 2016; 2016M891:1-5.

Yang W, Hu Y, Yang YS, Zhang F, Zhang YB, Wang XL, Tang JF, Zhong WQ, Zhu HL. Design, modification and 3D QSAR studies of novel naphthalin-containing pyrazolines derivatives with/without thiourea skeleton as anticancer agents. Bioorg and Med Chem. 2013; 21: 1050-1063

Koç GŞ, Tan OU, Uçar G, Yıldırım E, Erol K, Palaska E. Synthesis and monoamine oxidase inhibitory activities of some 3-(4-fluorophenyl)-5-aryl-N-substituted-4,5-dihydro-(1H)-pyrazole-1- carbothioamide derivatives. Drug Res. 2014; 64: 591–598.

Nimbalkar S, Bhoyar SP. Synthesis of some pyrazolines and their derivatives-a review. IJRITCC. 2015; 3 (2): 66-71.

Karabacak M, Altintop MD, Ciftci HI, Koga R, Otsuka M, Fujita M, Ozdemir A. Synthesis and evaluation of new pyrazoline derivatives as potential anticancer agents. Molecules. 2015; 20: 19066-19084.

Humprey W, Dalke A, Schulten K. VMD: visual molecular dynamics. J. Mol Graph. 1996; 14(1):33–38.

Yu-Meng X, Xing-Zhang H, Mezei M, Cui M. Molecular docking: a powerful approach for structure –based drug discovery. Curr comp aided drug des. 2011; 7(2): 146-157.

Wala SE, Neama AM, Emad MK, Mahmoud K, Mounier MM. Synthesis, Biological evaluation and docking analysis of some novel quinazolin derivatives as antitumor cancer. Iranian J of Pharm Res. 2016; 15 (1): 179-196.

Mubeen M, Kini SG, Pai KSR. Design, synthesis, antioxidant and anticancer activity of novel pyrazole derivatives. Der Pharma chemica. 2015; 7(2): 215-233.

Marzieh Y, Frimayanti N, Chee CF, Ikram KK, Najjar OB, Zain SM, Abdullah Z, Wahab HA. QSAR, insilico docking and in vitro evaluation of chalcone derivatives as potential inhibitors for H1N1 virus neurominidase. Med Chem Res. 2016; 25: 2133-2142.

Huiding X, Yupeng L, Fang Yu, Xiaoguang X, Kaixiong Q, Jijun F. An Investigation of Molecular Docking and Molecular Dynamic Simulation on Imidazopyridines as B-Raf Kinase Inhibitors. Int. J. Mol. Sci. 2015; 16: 27350–27361.


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