Syntheses and crystal structures of two piperine derivatives

Abstract

The title compounds, 5-(2H-1,3-benzodioxol-5-yl)-N-cyclohexylpenta-2,4-dienamide, C18H21NO3 (I), and 5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one C16H17NO3 (II), are derivatives of piperine, which is known as a pungent component of pepper. Their geometrical parameters are similar to those of the three polymorphs of piperine, which indicate conjugation of electrons over the length of the molecules. The extended structure of (I) features N—H...O amide hydrogen bonds, which generate C(4) [010] chains. The crystal of (II) features aromatic π–π stacking, as for two of three known piperine polymorphs.

Solubility of Piperine and Its Inclusion Complexes in Biorelevant Media and Their Effect on Attenuating Mouse Ileum Contractions

“…Raman spectroscopy easily detects different carbon–carbon bonds and has been used to evaluate differences in interactions between the GM and CP. The single-crystal X-ray analysis confirmed that the structure of PP does feature π–π stacking with the closest intermolecular contacts being carbon–carbon bonds . NIR and solid-state fluorescence measurements revealed that the molecular behavior of PP inside the α, β, and γCD cavities changed by water and heat factors depends on the mobility of the methylenedioxyphenyl group .…”

“…The single-crystal X-ray analysis confirmed that the structure of PP does feature π–π stacking with the closest intermolecular contacts being carbon–carbon bonds. 15 NIR and solid-state fluorescence measurements revealed that the molecular behavior of PP inside the α, β, and γCD cavities changed by water and heat factors depends on the mobility of the methylenedioxyphenyl group. 16 Also, from a Raman spectroscopy measurement, PP/αCD, PP/βCD, and PP/γCD inclusion complexes prepared by the GM method have been confirmed to suppress the motility of the methylenedioxyphenyl group and pentadiene chain that are hydrophobic parts of PP.…”

“…GM (PP/ βCD = 1/1) of the inclusion complex prepared by the ground mixture method lacked the characteristic crystal diffraction peak of PP. 15 On the other hand, CP (PP/βCD) showed characteristic diffraction peaks of head-to-head and head-to-tail (indicated by ◆) at 2θ = 11.7 and 15.3°, respectively, with PP-derived diffraction peaks seen at 2θ = 25.7°. 21,22 In the γCD system, PM (PP/γCD = 1/1) showed a characteristic diffraction peak of PP at 2θ = 25.6°.…”

“…The endothermic peak of the guest molecule disappeared upon the formation of the inclusion complex as previously reported by us for GM (PP/αCD = 1/2), GM (PP/βCD = 1/1), and GM (PP/γCD = 1/1). 15 − 17 Therefore, CP (PP/αCD) and CP (PP/γCD) formed an inclusion complex. 23 On the other hand, CP (PP/βCD) showed an endothermic peak corresponding to the PP melting point at approximately 131 °C.…”

“…The GM method utilizes the mechanochemical effect to prepare an inclusion complex by a solid–solid reaction . The preparation of inclusion complexes of PP with α-, β-, and γ-CDs using the GM method have already been reported. − The CP method uses an inclusion complex by a liquid–liquid reaction utilizing the difference in solubility between the drug and CD . Physical mixtures (PMs) were prepared for comparison with GMs and CPs.…”