Synthesis, Characterization, Spectroscopic, DFT and Molecular Docking Studies of 3-(3,4-Dihydroxyphenyl)-1-Phenyl-3-(Phenylamino)Propan-1-One

Abstract

The present work elucidates the synthesis, characterization of 3-(3,4-dihydroxyphenyl)-1-phenyl-3-(phenylamino)propan-1-onethrough Mannich type reaction using 1-hexyltriazolium methanesulfonate ionic liquid as catalyst. The synthesized molecule was functionally and structurally elucidated utilizing analytical techniques such as FT-IR, NMR, Mass and HPLC analysis were also carried out to establish the purity of target molecule. The computational studies, via optimization of molecular geometry, simulated vibrational frequency, NMR chemical shifts, UV-Vis absorbance, different partial atomic charges, surface analyses, FMO analyses, Fukui functions, reactivity descriptors, thermochemistry, NLO property, NBO analyses were also carried out using B3LYP/6-31G(d,p) basic set. The comparisons of all the experimental and their simulated spectral data for the target compound was made and which show good agreements with one another. All the computational attempts of the target molecule were made with the deep insights toward their future scope comprising with chemical reactivity, biological property, optical device applications, and so on. In addition, the molecular docking studies were also been carried out with three selected protein and the results reveals that the target compound is potential to interact with influenza neuraminidase and chikungunya nsP2 protease enzymes.

Keywords:

• Mannich reaction
• DFT
• NLO
• Fukui function
• NBO
• molecular docking

Acknowledgements

The author VV thanks to Department of Chemistry, Anna University, Department of Chemistry Karan Arts and Science College, for continues support and encouragement.

Disclosure statement

The authors declare no competing financial or personal interests.