A series of three 1,3-phenylene bis-oxamides
3a–
c, structurally related to the GPR35 receptor-agonist drug lodoxamide, has been synthesized by reacting the 1,3-phenylene bis-oxalamates
2a and
2b with amines. The obtained compounds were characterized by
1H and
13C NMR,
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A series of three 1,3-phenylene bis-oxamides
3a–
c, structurally related to the GPR35 receptor-agonist drug lodoxamide, has been synthesized by reacting the 1,3-phenylene bis-oxalamates
2a and
2b with amines. The obtained compounds were characterized by
1H and
13C NMR, and IR spectroscopy, they showed characteristic signals for the aromatic, N―H, and C=O groups. Molecular structure was determined using single-crystal X-ray diffraction. The supramolecular architecture is driven by N―H···O=C, N―H···N, C—H···π, and O=C···O=C interactions depicting a supramolecular helix (
3a) and tapes (
3b–
c). Intermolecular interactions were studied using Hirshfeld surface analysis, where N―H∙∙∙X (X = N, O) hydrogen bonding represents 30.2% to the surface of
3a and 17.8–18.8% to the surface of
3b–
c. The most energetic interactions involve the amide N—H∙∙∙O hydrogen bonding, contributing in the −113.9 to −97.0 kJ mol
−1 range to the crystal energy, being more dispersive than electrostatic in nature. The molecular docking study was performed to evaluate the binding ability of
3a–
c compounds to the GPR35 receptor, showing a favorable binding in a similar way to lodoxamide.
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