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Tuning the molecular/electronic structure of new substituted pyrazoles: Synthesis, biological trials, theoretical approaches and Hammett correlations

dc.contributor.authorBustos C.
dc.contributor.authorAlvarez-Thon L.
dc.contributor.authorMolins E.
dc.contributor.authorMoreno-Villoslada I.
dc.contributor.authorVallejos-Contreras G.
dc.contributor.authorSánchez C.
dc.contributor.authorZarate X.
dc.contributor.authorMac-Leod Carey D.
dc.contributor.authorSchott E.
dc.date.accessioned2020-09-02T22:13:37Z
dc.date.available2020-09-02T22:13:37Z
dc.date.issued2018
dc.identifier10.1016/j.molstruc.2018.05.088
dc.identifier.citation1171, , 349-361
dc.identifier.issn00222860
dc.identifier.urihttps://hdl.handle.net/20.500.12728/3813
dc.descriptionThe high yield synthesis, characterization and biological trials of a family of compounds containing the pyrazole core (E)-3,5-dimethyl-1-(4-R-phenyl)-4-(phenyldiazenyl)-1H-pyrazoles (with R = 4-CH3O (1), 4-CH3 (2), 4-H (3), 4-F (4), 4-Cl (5), 4-CF3 (6), 4-CN (7), 4-NO2 (8), 3-Cl (9), 3-NO2 (10), 2-Cl (11) and –C6F5 (12)) are reported. Hammett correlations were found for the experimental and theoretical computed data, showing the dependence of all the obtained results on the donor or acceptor nature of the R substituent. In this sense, the absorption wavelength does decrease as the electron-withdrawing character of the substituent increases. Furthermore, the wavelength intensity does follow a Hammett correlation with the sigma donor character of the substituents. The compounds were characterized using MP, EA, UV–vis, FT-IR, 1H NMR, 13C NMR including bidimensional NMR experiments (HMBC and HMQC). The structures of 4, 5 and 8 were successfully elucidated by means of X-Ray diffraction. Pyrazole based dyes are known in pharmacological areas. Therefore, biological activity of all these structures were tested against cancer cell lines over a wide library of cell lines (60), including leukemia, colon and brain cancer, showing that the compounds have anticancer activity, which expands the knowledge of this kind of dyes as targets for this critical application. Finally, quantum calculations were carried out in order to give a rational explanation to the observed UV–vis absorption bands and FT-IR signals. As shown, it is possible to tune the molecular/electronic structure of the synthesized dyes by means of changing the –R substituent in the structure. © 2018 Elsevier B.V.
dc.language.isoen
dc.publisherElsevier B.V.
dc.subjectAnticancer activity
dc.subjectDFT
dc.subjectHammett correlation
dc.subjectPyrazoles
dc.subjectSynthesis
dc.subjectBioactivity
dc.subjectCell culture
dc.subjectDiseases
dc.subjectNuclear magnetic resonance spectroscopy
dc.subjectSynthesis (chemical)
dc.subjectAbsorption wavelengths
dc.subjectAnticancer activities
dc.subjectCritical applications
dc.subjectHammett correlation
dc.subjectHigh yield synthesis
dc.subjectPyrazoles
dc.subjectSubstituted pyrazoles
dc.subjectTheoretical approach
dc.subjectBrain
dc.titleTuning the molecular/electronic structure of new substituted pyrazoles: Synthesis, biological trials, theoretical approaches and Hammett correlations
dc.typeArticle


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