One Pot Efficient Synthesis of 1,3-di(Naphthalen-1-yl)Thiourea; X-Ray Structure, Hirshfeld Surface Analysis, Density Functional Theory, Molecular Docking and In-Vitro Biological Assessment

Muhammad Asam Raza, Kanwal Javaid, Umme Farwa, Anam Javaid, Muhammad Yaseen, Jan K. Maurin, Armand Budzianowski, Bushra Iqbal, Saba Ibrahim,

https://doi.org/10.1016/j.molstruc.2022.133989
Supplementary information

Highlights

  • A new thiourea has been prepared using one pot synthesis.
  • Structure elucidation was done with XRD.
  • In-Vitro enzyme inhibition and antibacterial assessments.
  • DFT and Docking studies used to compare experimental and theoretical calculations.

Abstract

1,3-di(Naphthalen-1-yl)Thiourea was synthesized in good yield from a cheaper amine through one pot synthesis technique. The exact structure was elucidated with single crystal X-ray Diffraction. In silico studies in terms of Hirshfeld analysis, density functional theory and molecular docking were carried out. The thiourea was optimized with hybrid functional B3LYP method and 6-31G(d,p) basis set. Bond angles and bond lengths determined from XRD were compared with these obtained from DFT and are in close agreement to each other. The HOMO (highly occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) energy gap is 4.915 eVIn 2D fingerprinting analysis (Hirshfeld), H∙∙∙H contacts are responsible for the stability of the crystalline structure. The antibacterial studies against five different strains depicted good potential of the thiourea toward tested bacteria. The enzyme inhibition potential of the compound was determined against esterase which concluded that understudied molecule has ability to inhibit both enzymes with good efficiency. Furthermore, docking analysis also supported the spectrophotometric results of the compound toward enzyme inhibition. On the basis of the biological studies either in term of wet or dry lab, it was concluded that synthesized compound has much potential to use as therapeutic agent in the future.

    Keywords: Density Functional Theory; Docking; Crystal Structure; Acetylcholine Esterase; Butyrylcholine Esterase

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