Synthesis and Characterization of New N‐Pyrazol‐5‐yl) amidine Derivatives: X‐Ray Structure Hirshfeld Surface, and DFT Analyses together with Antibacterial and Antifungal Activity Studies

Abstract

We present in this work, the synthesis and characterization of N‐3‐pyrazolyl amidines derivatives obtained in satisfactory yields via one‐pot reaction. New structures of amidines were confirmed by FTIR, 1H NMR, 13C NMR, 13C NMR Dept spectrum and X ray crystallography of N‐benzyl‐N‐(3‐methyl‐1H‐pyrazol‐5‐yl) propanimidamide. In order to determinate the configuration of this amidine we have characterized it using also HRMS, DSC to determine the fusion points, X‐ray crystallography and Hirshfeld Surface analysis. The grown crystal possesses a dielectric behavior and DFT Calculation which has shown linear correlation between theoretical and experimental Hydrogen bond geometry, bond lengths (A°) and Torsion angles of 1 a. The examination of the spectrum and the SEM diagram of amidine 1a allowed us to determine the size of the particles which is of the order of 1.8 μm. All new amidines were screened for their antibacterial and antifungal activities and their phenotypic analysis was performed using the Phenotype Micro Arrays (PMs) tool to determine cellular responses during their respiration process. Amidines had relatively antibacterial activities with an antifungal behavior proving their interface reaction with several microrganisms. Such finding can be useful in medical and agricultural fields. The considered species belong to human's gut flora and soil phytopathogenesis fungi.

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“…Amidines are important compounds that are widely used in the field of catalyst design, 1,2 materials science 3 and medicinal chemistry. 4–7 The amidino group in 1a , which contains an amino nitrogen atom with a free electron pair conjugated with the π-electrons of the CN double bond, combines the properties of an azomethine-like CN double bond with an amide like C–N single bond with a partial double bond character as indicated by the resonance form 1b 8 (see Scheme 1).…”