Interprofessional Journal of Health Sciences. Vol.17 No.2 , July - December 2019.

SYNTHESIS AND ANTI-CERVICAL ACTIVITY OF 3-CHLORO-N-PHENYLBENZAMIDE

Thitaree Theerachayanan and Anong Teeravanichpong

Abstract

Targeted chemotherapy is one of the popular cancer treatments. Many studies had shown that enzyme IKKβ is one of the key elements which essential for activation of cell proliferation in the NF-kB signaling pathways.  Therefore, this enzyme was utilized as target for activity inhibition. The 3-Chloro-N-phenylbenzamide, an aryl amide compound, was designed and synthesized as a small molecule aimed to act as IKKβ inhibitor and possess anti-proliferative activity.  The compound was simulated and docking with IKKβ enzyme by computer-aided process to evaluate for its potential therapeutic properties.  The structure of this compound was characterized by spectroscopic methods.  The results from infrared spectrum showed a singlet peak of secondary amine at wavenumber 3,352 cm^-1 and a carbonyl amide peak at wavenumber 1,659 cm^-1.  The ¹H Nuclear Magnetic Resonance spectrum showed two distinct regions of 10 protons; the –NH peak at 10.37 ppm and another nine aromatic protons in the range of 7.10 – 8.03 ppm.  The fragmentation pattern from mass spectrum showed the remarkable base peak at m/z 135.2 which is the typical of benzoyl fragment peak with the molecular ion peak also corresponding with the molecular weight of compound which equals to 231. An MTT assay indicated the ability of the synthesized compound that can inhibit the growth of cervical cancer cell line (SiHa) with an IC₅₀ of 22.4 µM.  The result emphasized the possibility of targeted cancer therapy of this compound.

Keywords: Aryl amide, Anticancer, Targeted chemotherapy, Benzamide, IKKβ inhibitor

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