Synthesis, Characterization, X-ray Diffraction Studies, and Biological Evaluation of Tert-butyl 4-(5-(3-fluorophenyl)-1,2,4-oxadiazol-3-yl) piperazine-1-carboxylate

Abstract

The title compound tert-butyl 4-(5-(3-fluorophenyl)-1,2,4-oxadiazol-3-yl)piperazine-1-carboxylate was synthesized by condensation reaction between carbamimide and 3-fluorobenzoic acid in the presence of 3-(3-dimethylaminopropyl)carbodiimide hydrochloride and hydroxybenzotriazole under basic condition. It was characterized by spectroscopic evidences such as LCMS, ¹H NMR, ¹³C NMR, IR, and CHN elemental analysis. The structure was further confirmed by single crystal XRD data. The title compound, C₁₇H₂₁FN₄O₃, crystallized in the monoclinic crystal system and P2₁/c space group with the unit cell parameters a = 14.281(3) Å, b = 11.579(2) Å, c = 11.331(2) Å, β = 110.674(6)°, Z = 4, and V = 1753.0(6) ų. In the structure, the molecules are linked through weak C‒H···O intermolecular interactions along [010], and aromatic π–π stacking interactions (centroid-centroid distance = 3.7456(15)Å generate a three-dimensional architecture. The compound was screened for its in vitro antibacterial and anthelmintic activity. The compound exhibited poor antibacterial and moderate anthelmintic activity.

Keywords:

• 1,2,4-oxadiazole
• anthelmintic activity
• antibacterial activity
• XRD