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Convenient Synthesis and Characterization of Novel Phytosteroid Derivatives and Their DFT, QTAIM, NCI–RDG, and Molecular Docking Study: A Combined Experimental and Theoretical Approach

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Abstract

The synthesis of novel steroid derivatives by the F ring opening in diosgenin in the presence of BF3∙OEt2 as a catalyst have been reported. The structural assignment of the synthesized compounds was performed by means of FTIR and 1H, 13C, and 2D NMR spectroscopy and ESI–HRMS and confirmed by DFT/B3LYP calculations. Hydrogen bonding and other multiple interactions were analyzed in detail in terms of Bader’s theory of atoms in molecules. The NCI–RDG analysis gave evidence showing that derivatives are stabilized by a series of weak C–H∙∙∙O hydrogen bonds and C–H and H–H interactions. The reactivity descriptors and MEP analysis allowed identification of the reactive sites in the studied molecules. The energy gap and ionization energy of synthesized derivatives have also been calculated to identify chemical reactivity. The molar refractivities of the products were estimated at 109–153.98 esu, implying the ability of the synthesized compounds to bind target protein and their potential as candidate drugs.

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CONFLICT OF INTEREST

The authors declare no conflict of interest.

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Authors and Affiliations

  1. Department of Chemistry, University of Lucknow, 226007, Lucknow, India

    P. Singh, P. Rawat, P. Yadav, A. Singh, A. Yadav & A. Sethi

  2. Department of Applied Science & Humanities, Faculty of Engineering & Technology, University of Lucknow, 226031, Lucknow, India

    R. P. Singh

  3. Department of Chemistry, Institute of Natural Sciences, Shri Ramswaroop Memorial University, 225003, Barabanki, India

    R. Prakash

  4. Department of Applied Science & Humanities, Institute of Engineering & Technology, 226021, Lucknow, India

    S. Srivastava

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Singh, P., Singh, R.P., Prakash, R. et al. Convenient Synthesis and Characterization of Novel Phytosteroid Derivatives and Their DFT, QTAIM, NCI–RDG, and Molecular Docking Study: A Combined Experimental and Theoretical Approach. Russ J Org Chem 59, 1382–1396 (2023). https://doi.org/10.1134/S1070428023080134

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