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Spectroscopic, computational DFT, in vitro, and molecular docking investigations of newly isolated 2, 3, 9, and 10-tetrahydroacridin-3-one from the methanolic extract of nilavembu kudineer chooranam

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Abstract

The Gaussian09 program was studied by using the optimized molecular structure with vibrational frequency assignments of 2, 3, 9, and 10 tetrahydroacridin-3-one (abbreviated as THA-3-one). The VEDA software is used to compute the potential energy distribution of the vibrational modes. The optimized geometrical parameters were in agreement with related derivatives. Time-dependent density functional theory estimates oscillator strength and energy, which are almost in line with experimental discoveries. In order to accomplish the gauge-including atomic orbital 1H and 13CNMR chemical shift predictions, the B3LYP functional with 6–311 +  + G (d, p) basis sets was utilized. The charge movement within the compound is determined using the HOMO and LUMO investigations. The MEP was revealed using the DFT approach, and the infrared intensities have also been published. Milliken net charges are contrasted with the atomic natural charges. In vitro biological THA-3-one was discovered potent bactericidal activity with a maximum of (20.5 ± 1.0 mm) at 2.5 µg/mL against Yersinia enterocolitica (MTCC 840) and showed a maximum scavenging property of 73.9 ± 1.5% at the highest concentrations of 1000 μg/ML and also showed a maximum scavenging property of 73.9 ± 1.5% at the highest concentrations of 1000 μg/mL, respectively (p < 0.05). In silico molecular docking showed that ligand interacts with (PDB Code: 5AA9) protein by using AutoDock software, which exhibits a lower binding energy assessment of − 6.8 (Kcal/mol) and inhibition constant (ki) value of 10.234 μM.

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Acknowledgements

The authors are thankful to Dr. G. JeyaJothi, Taxnomist, Department of plant Biology and Biotechnology, Loyola College, Chennai, for the authentication of the plant species. The authors thank J. Irshad Ahamed and P. Kamalarajan for kindly providing us access to the all spectral studies for performing the experiments. The authors also thank R. Priya & M. F. Valan for kindly providing the molecular docking studies.

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The authors confirm that they have no known financial or interpersonal conflicts that may have looked to have influenced the research presented in this study.

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Authors and Affiliations

  1. Department of Chemistry, LIFE (Loyola Institute of Frontier Energy), Loyola College, University of Madras, Nungambakkam, Chennai, Tamil Nadu, 600034, India

    P. Kamalarajan, J. Irshad Ahamed & M. F. Valan

  2. Department of Chemistry, C. Kandaswami, Naidu College for Men, Anna Nagar East, Chennai, Tamil Nadu, 600102, India

    J. Irshad Ahamed

  3. Department of Physics, R.M.D. Engineering College, Kavaraipettai, 601206, India

    R. Priya

  4. Department of Chemistry, R.M.D Engineering College, Kavaraipettai, Tamil Nadu, 601206, India

    P. Kamalarajan

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  1. P. Kamalarajan
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J. Irshad Ahamed was responsible for conceptualization, investigation, writing the original draft, and writing, reviewing, and editing. P. Kamalarajan took part in investigation and writing. R. Priya and M. F. Valan contributed to molecular docking and DFT computational studies.

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Correspondence to P. Kamalarajan.

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Kamalarajan, P., Irshad Ahamed, J., Priya, R. et al. Spectroscopic, computational DFT, in vitro, and molecular docking investigations of newly isolated 2, 3, 9, and 10-tetrahydroacridin-3-one from the methanolic extract of nilavembu kudineer chooranam. Res Chem Intermed 49, 2669–2690 (2023). https://doi.org/10.1007/s11164-022-04906-3

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