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Synthesis, characterization and preliminary study on acetylpyrazine N(4)butylthiosemicarbazone as a potential CDK2 inhibitor combined with DFT calculations

Abdullah, Erna Normaya and Ahmad, Mohammad Norazmi and Abdul Aziz, Yang Farina and Ku Bulat, Ku Halim (2018) Synthesis, characterization and preliminary study on acetylpyrazine N(4)butylthiosemicarbazone as a potential CDK2 inhibitor combined with DFT calculations. Journal of Brazilian Chemical Society, 29 (10). pp. 2197-2206. ISSN 0103-5053 E-ISSN 1678-4790

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Abstract

In this study, a new thiosemicarbazone ligand, namely acetylpyrazine N(4)butylthiosemicarbazone (APBT), was synthesized and characterized using 1H and 13C nuclear magnetic resonance (NMR) and Fourier transform infrared (FTIR) spectroscopies. Quantum chemical calculations were performed using density functional theory at the B3LYP/6-311++G(d,p) basis set level. The optimized molecular geometry of APBT is discussed based on X-ray structural reports from the literature. The assignment of the vibrational frequencies was done based on a potential energy distribution analysis using the vibrational energy distribution analysis (VEDA) 4 software. The energy gap between the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) was evaluated to study the reactivity and stability of the compound. Global chemical reactivity and local reactivity descriptors of reactants and the product (APBT) were calculated to study the reaction mechanism. The region of interaction during the reaction to form APBT was determined using molecular electrostatic potential analysis. Finally, a preliminary study of the title compound as a cyclin-dependent kinase (CDK) inhibitor was further evaluated by performing a docking calculation.

Item Type: Article (Journal)
Additional Information: 7149/63804
Uncontrolled Keywords: thiosemicarbazone, DFT, global reactivity descriptors, CDK inhibitor
Subjects: Q Science > QD Chemistry
Kulliyyahs/Centres/Divisions/Institutes (Can select more than one option. Press CONTROL button): Kulliyyah of Science > Department of Chemistry
Depositing User: Dr Erna Normaya Abdullah
Date Deposited: 23 May 2018 10:50
Last Modified: 15 Feb 2019 11:55
URI: http://irep.iium.edu.my/id/eprint/63804

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