Synthesis of Biologically Active α-Tetralone Condensate: Growth of Single Crystal, Characterization by Experimental and Simulation Methods

Abstract

The exocyclic double bonded α-tetralone condensate viz. (2E)-2-(4-propoxybenzylidene)-3,4-dihydro-1(2H)-naphthalene-1-one was synthesized by the Claisen–Schmidt reaction between α-Tetralone and 4-propoxybenzaldehyde in an alkaline medium. A slow evaporation technique was used to collect the single crystals. Researchers examined the detailed information provided by spectral studies. The inter- and intra-molecular interactions of the compound were identified using the single-crystal XRD investigation. Charge transfer inside organic molecules was used to calculate HOMO and LUMO energy values. In addition, MEP, NBO, NLO, topological charge distribution, and Mulliken population studies were performed for this compound. The Hirschfeld surface study showed that nonpolar or weakly polar interactions significantly contributed to the packing forces for molecules. Then, it was tested for its antioxidant, antidiabetic, and anti-inflammatory properties. The 6yb7 protein and the (2E)-2-(4-propoxybenzylidene)-3,4-dihydro-2H-naphthalen-1-one (PBDN) ligand were docked in molecular docking research.

Highlights

• Crystal growth and spectral studies have been performed on (2E)-2-(4-propoxybenzylidene)-3,4-dihydro-2H-naphthalen-1-one (PBDN).

• Simulation studies were discussed.

• The compound PBDN has potential anti-inflammatory and anti-diabetic properties.

• In-silico method reveals that the PBDN is a moderate ligand for an unliganded active site on COVID-19’s main protease (PDB code: 6yb7).

Keywords:

• α-Tetralone condensate
• single crystal
• DFT
• in-vitro
• in-silico

Disclosure statement

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this article.

Author contributions

N. Afsar: Conceptualization; Data curation; Formal analysis; Investigation; Validation; Writing - original draft. D. Reuben Jonathan: Conceptualization; Formal analysis; Investigation; Visualization. S. Manivannan: Supervision; review & editing. J. Irshad Ahamed: Writing – review & editing.