Investigation of Anticancer Properties of 2-benzylidene-1-indanone and Its Derivatives by DFT and Molecular Docking-Reference-Cited by-同舟云学术

Investigation of Anticancer Properties of 2-benzylidene-1-indanone and Its Derivatives by DFT and Molecular Docking

Published:2024-05-21 Issue:2 Volume:8 Page:101-109
ISSN:2587-1722
Container-title:Turkish Computational and Theoretical Chemistry
language:
Short-container-title:

Author:

Alkaya Yıldız Ceylan¹^ORCID,Erkan Sultan¹^ORCID

Affiliation:

1. SIVAS CUMHURIYET UNIVERSITY, FACULTY OF SCIENCE, CHEMISTRY PR.

Abstract

In this study, 2-benzylidene-1-indanone and its derivatives, which is a chalcone compound and contains indanone in its structure, were examined. Quantum chemical parameters for these compounds were calculated with the B3LYP method and the 6-31G(d) basis set and evaluated for their biological activity. The effect of different functional groups (F, Cl, Br, CF3, CH3 and OCH3) attached to the 2-benzylidene-1-indanone compound on biological activity was investigated. Some quantum chemical parameters such as highest energy filled molecule orbital energy (EHOMO), lowest non-bonding empty molecule orbital energy (ELUMO), energy gap (ΔE), hardness (η), softness (σ), global molecular electrophilicity (ω) index, global molecular nucleophilicity (ɛ) index, electron-accepting (ω+) and electron-donating (ω-) electrophilicity index were calculated for the biological activities of the compounds. Frontier molecular orbitals and molecular electrostatic potential (MEP) maps were interpreted. The biological activities of 2-benzylidine-1-indanone and some of its derivatives bearing the 1-indanone skeleton were evaluated by performing molecular docking studies with the target protein PDB ID = 1HJD corresponding to the melanoma cell line. The activity ranking obtained with quantum chemical parameters was found to be compatible with the binding energies obtained from docking results.

Publisher

Turkish Computational and Theoretical Chemistry

Reference29 articles.

1. [1] Shrestha, A., Oh, H. J., Kim, M. J., Pun, N. T., Magar, T. B. T., Bist, G., ... & Lee, E. S. (2017). Design, synthesis, and structure-activity relationship study of halogen containing 2-benzylidene-1-indanone derivatives for inhibition of LPS-stimulated ROS production in RAW 264.7 macrophages. European Journal of Medicinal Chemistry, 133, 121-138.

2. [2] Shintani, E. Y., & Uchida, K. M. (1997). Donepezil: an anticholinesterase inhibitor for Alzheimer’s disease. American journal of health-system pharmacy, 54(24), 2805-2810.

3. [3] Xiao, S., Zhang, W., Chen, H., Fang, B., Qiu, Y., Chen, X., ... & Liang, G. (2018). Design, synthesis, and structure–activity relationships of 2-benzylidene-1-indanone derivatives as anti-inflammatory agents for treatment of acute lung injury. Drug Design, Development and Therapy, 12, 887.

4. [4] Xiao, S., Zhang, W., Chen, H., Fang, B., Qiu, Y., Chen, X., ... & Liang, G. (2018). Design, synthesis, and structure–activity relationships of 2-benzylidene-1-indanone derivatives as anti-inflammatory agents for treatment of acute lung injury. Drug Design, Development and Therapy, 12, 887.

5. [5] Gezegen, H., Tutar, U., Hepokur, C., Tüzün, G., Atioğlu, Z., & Akkurt, M. (2021). Michael/Michael Addition Cascade of 2‐Benzylidene‐1‐indanones with Chalcones: Synthesis and Biological Evaluations of Novel Polycyclic Compounds. ChemistrySelect, 6(36), 9625-9631.