Shedding Light on the Synthesis, Crystal Structure, Characterization, and Computational Study of Optoelectronic Properties and Bioactivity of Imine derivatives

Muhammad Ashfaq; Muhammad Nawaz Tahir; Shabbir Muhammad; Khurram Shahzad Munawar; Saqib Ali; Gulzar Ahmed; Abdullah G Al-Sehemi; Saleh S Alarfaji; Muhammad Ehtisham Ibraheem Khan

doi:10.1021/acsomega.1c06325

Shedding Light on the Synthesis, Crystal Structure, Characterization, and Computational Study of Optoelectronic Properties and Bioactivity of Imine derivatives

ACS Omega. 2022 Feb 2;7(6):5217-5230. doi: 10.1021/acsomega.1c06325. eCollection 2022 Feb 15.

Authors

Muhammad Ashfaq¹, Muhammad Nawaz Tahir¹, Shabbir Muhammad², Khurram Shahzad Munawar³, Saqib Ali⁴, Gulzar Ahmed⁵, Abdullah G Al-Sehemi², Saleh S Alarfaji², Muhammad Ehtisham Ibraheem Khan⁶

Affiliations

¹ Department of Physics, University of Sargodha, Sargodha 40100, Pakistan.
² Department of Chemistry, College of Science, King Khalid University, P.O. Box 9004, Abha 61413, Saudi Arabia.
³ Institute of Chemistry, University of Sargodha, Sargodha 40100, Pakistan.
⁴ Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan.
⁵ School of Materials Science and Engineering, South China University of Technology, Guangzhou 510640, China.
⁶ Department of Chemistry, University of Wah, Quaid Avenue Wah Cantt., Rawalpindi 47040, Pakistan.

Abstract

Two imine compounds named as (E)-2-(((3,4-dichlorophenyl)imino)methyl)phenol (DC2H) and (E)-4-(((2,4-dimethylphenyl)imino)methyl)phenol (DM4H) are synthesized, and their crystal structures are verified using the single-crystal X-ray diffraction (XRD) technique. The crystal structures of the compounds are compared with the closely related crystal structures using the Cambridge Structural Database (CSD). The crystal packing in terms of intermolecular interactions is fully explored by Hirshfeld surface analysis. Void analysis is carried out for both compounds to check the strength of the crystal packing. Furthermore, a state-of-the-art dual computational technique consisting of quantum chemical and molecular docking methods is used to shed light on the molecular structure, optoelectronic properties, and bioactivity of indigenously synthesized compounds. The optimized molecular geometries are compared with their counterpart experimental values. Based on previous reports of biofunctions of the indigenously synthesized imine derivatives, they are explored for their potential inhibition properties against two very crucial proteins (main protease (M^pro) and nonstructural protein 9 (NSP9)) of SARS-CoV-2. The calculated interaction energy values of DC2H and DM4H with M^pro are found to be -6.3 and -6.6 kcal/mol, respectively, and for NSP9, the calculated interaction energy value is found to be -6.5 kcal/mol. We believe that the current combined study through experiments and computational techniques will not only pique the interest of the broad scientific community but also evoke interest in their further in vitro and in vivo investigations.