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A novel series of pyrazole derivatives toward biological applications: experimental and conceptual DFT characterization

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Abstract

A new series of 13 pyrazole-derivative compounds with potential antifungal activity were synthetized with good yields. The series have the (E)-2-((1-(R)-3,5-dimethyl-1H-pyrazol-4-yl)diazenyl)phenol general structure and were characterized by means of X-ray diffraction, UV–Vis, FTIR, 1H-NMR, 13C-NMR, and two-dimensional NMR experiments. This experimental characterization was complemented by DFT simulations. A deep insight regarding molecular reactivity was accomplished employing a conceptual DFT approach. In this sense, dual descriptors were calculated at HF and DFT level of theory and GGV spin-density Fukui functions. The main reactive region within the molecules was mapped through isosurface and condensed representations. Finally, chemical descriptors that have previously shown to be close related to biological activity were compared within the series. Thus, higher values of chemical potential ω and electrophilicity χ obtained for compounds 10, 9, 8, 6 and 7, in this order, suggest that these molecules are the better candidates as biological agents.

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Acknowledgements

Grants Fondecyt 1180565, 1201880, 11200677, and 3210559. ANID/FONDAP/15110019.

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Authors and Affiliations

  1. Instituto de Ciencias Químicas Aplicadas, Facultad de Ingeniería, Universidad Autónoma de Chile, Llano Subercaseaux, 2801, Santiago, Chile

    Pedro D. Ortiz & Ximena Zarate

  2. Departamento de Química Inorgánica, Facultad de Química y Farmacia, Centro de Energía UC, Centro de Investigación en Nanotecnología y Materiales Avanzados CIEN-UC, Pontificia Universidad Católica de Chile, Avenida Vicuña Mackenna, 4860, Santiago, Chile

    Judith Castillo-Rodriguez, Vanesa Roa & Eduardo Schott

  3. Departamento de Ciencias Quı́micas y Biológicas, Universidad Bernardo O’Higgins, Facultad de Salud, General Gana, 1702, Santiago, Chile

    Jorge Tapia

  4. Instituto de Ciencias Químicas, Universidad Austral de Chile, Las Encinas 220, Campus Isla Teja, Valdivia, Chile

    Gabriel A. Vallejos & Carlos Bustos

  5. Institut de Ciència de Materials de Barcelona (ICMAB-CSIC), Campus UAB, 08193, Bellaterra, Spain

    Elies Molins

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  1. Pedro D. Ortiz
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Ortiz, P.D., Castillo-Rodriguez, J., Tapia, J. et al. A novel series of pyrazole derivatives toward biological applications: experimental and conceptual DFT characterization. Mol Divers 26, 2443–2457 (2022). https://doi.org/10.1007/s11030-021-10342-z

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