Structural and Theoretical Investigations, Hirshfeld Surface Analyses, and Cytotoxicity of a Naphthalene-Based Chiral Compound

Saud I Al-Resayes; Mohammad Azam; Agata Trzesowska-Kruszynska; Rafal Kruszynski; Saied M Soliman; Ranjan K Mohapatra; Zahid Khan

doi:10.1021/acsomega.0c03376

Structural and Theoretical Investigations, Hirshfeld Surface Analyses, and Cytotoxicity of a Naphthalene-Based Chiral Compound

ACS Omega. 2020 Oct 12;5(42):27227-27234. doi: 10.1021/acsomega.0c03376. eCollection 2020 Oct 27.

Authors

Saud I Al-Resayes¹, Mohammad Azam¹, Agata Trzesowska-Kruszynska², Rafal Kruszynski², Saied M Soliman³, Ranjan K Mohapatra⁴, Zahid Khan⁵

Affiliations

¹ Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
² Institute of General and Ecological Chemistry, Lodz University of Technology, Zeromskiego 116, Lodz 90-924, Poland.
³ Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt.
⁴ Department of Chemistry, Government College of Engineering, Keonjhar, Odisha 758002, India.
⁵ Genome Research Chair, Department of Biochemistry, College of Science, King Saud University, Riyadh 11451, Saudi Arabia.

Abstract

A novel Schiff base compound derived from the condensation of 2-hydroxy-1-naphthaldehyde with (1S,2S)-(-)-1,2-diphenylethylenediamine in 2:1 M ratio was reported and investigated by elemental analyses, Fourier transform infrared and NMR spectroscopic studies, and single-crystal X-ray crystallography. Hirshfeld surface analyses were also carried out to measure the various intermolecular contacts controlling the supramolecular topology, suggesting the H···O (7.6%) contacts to be the most significant interactions, whereas the H···H (48.9%) and C···H (40.2%) interactions are less-significant. The data obtained from the energy calculations revealed the structure observed experimentally to be the most stable isomer and its energy being lower by 18.0441 kcal/mol than the less stable one. Density functional theory calculations were also carried out to analyze the natural charges, reactivity descriptors, and different intramolecular charge transfer interactions. The in vitro anticancer activity of the compound was evaluated by MTT assays against human colorectal cancer cells, HT-29 and SW620. The results showed that the compound has potential anticancer activity against these cells lines.