Structural description, IR, TGA, antiradical, HRP activity inhibition and molecular docking exploration of N-cyclohexyl-N-tosylformamide

Abstract

The synthesis and full characterization of new N-cyclohexyl-N-tosylformamide (10) is presented in this work. In addition to NMR and mass spectrometry, the thermal stability of 10 was explored using thermogravimetric analysis. Finally, the molecular structure of 10 was obtained by X-ray diffraction analysis. Compound 10 crystallizes with two molecules per asymmetric unit in the monoclinic system with C2 space group. The unit cell parameters is characterized by a = 19.0958(17) Å, b = 5.7763(6) Å, c = 25.341(2) Å, a volume of 2741.7(4) Å3, an angle β = 101.228(4) ° and Z = 8. The crystal packing is stabilized by intermolecular hydrogen bonds. The intermolecular contacts were further analyzed by the mapping of contacts descriptors dnorm, de, di, the shape by shape index and surface property by electrostatic potential mapped on the Hirshfeld surface. The mapping of 2D fingerprint of the title compound reveals that the most important contributions in the global contacts are dominated by H···H (62.4%) followed by O···H (24.0%) interactions. The radical scavenging activity of the title compound was explored and results in both DPPH and ABTS assay reveal moderate antioxidant activity. Nevertheless, compound 10 showed an interesting potency to inhibit HRP peroxidase activity. The result of peroxidase inhibitory activity is confirmed by molecular docking study showing interactions of 10 with HRP residues especially with Arg38 and Pro141 of the binding domain.