Synthesis, characterization, crystal and molecular structure and theoretical study of N-(naphthalen-1-yl)-2-(piperidin-1-yl) acetamide, a selective butyrylcholinesterase inhibitor

dc.creatorCamargo-Ayala, Lorena
dc.creatorPrent-Pe?aloza, Luis
dc.creatorPolo-Cuadrado, Efra?n
dc.creatorBrito, Iv?n
dc.creatorCisterna, Jonathan
dc.creatorOsorio, Edison
dc.creatorGonz?lez, Wendy
dc.creatorGuti?rrez, Margarita
dc.date2022-08-30T20:23:01Z
dc.date2022-08-30T20:23:01Z
dc.date2022-01-15
dc.date.accessioned2023-08-31T19:25:00Z
dc.date.available2023-08-31T19:25:00Z
dc.identifierCamargo-Ayala, L., Prent-Pe?aloza, L., Polo-Cuadrado, E., Brito, I., Cisterna, J., Osorio, E., . . . Guti?rrez, M. (2022). Synthesis, characterization, crystal and molecular structure and theoretical study of N-(naphthalen-1-yl)-2-(piperidin-1-yl) acetami
dc.identifier0022-2860
dc.identifierhttps://www.sciencedirect.com/science/article/abs/pii/S0022286021016720
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/8558128
dc.descriptionIn this study, we reported for the first time the crystalline and molecular structure of the compound N-(naphthalen-1-yl) -2- (piperidin-1-yl) acetamide. The synthesis of the compound was carried out by amidation using a coupling reagent (N, N'-diisopropylcarbodiimide) and subsequently amination. The compound was experimentally characterized by UV-visible spectroscopy, 13C-NMR, 1H-NMR, melting point, and X-ray diffraction technique. In addition, we include here, theoretical studies on boundary molecular orbitals, descriptors global reactivity, natural bond orbital analysis, Hirshfeld surface analysis, energy framework and molecular docking. Interestingly, acetamide shows a keto form in the solid state, as reported in similar monosubstituted acetamide compounds. The dihedral angles are negligible, being essentially coplanar between the fragment. Additionally, inhibitory activity studies were carried out for the enzymes acetylcholinesterase and butyrylcholinesterase, obtaining an IC50 of 426.14 ? 18.54 ?M and 5.12 ? 0.02 ?M, respectively, thus having significant selectivity for butyrylcholinesterase with an IC50 lower than that reported for the reference compound galantamine (7.96 ? 0.8 ?M). Our consistent molecular coupling analyzes show the formation of a more stable complex between compound 5 and butyricholinesterase due to the complementary interactions of compound 5?s naphthyl ring with residues Trp 231 and Phe 329 compared to the complex formed with acetylcholinesterase.
dc.descriptionUniversidad de Ibagu?
dc.languageen
dc.publisherJournal of Molecular Structure
dc.subjectAlzheimer disease
dc.subjectCholinergic enzymes
dc.subjectComputational analyzes
dc.subjectCrystal structure
dc.subjectMolecular docking
dc.titleSynthesis, characterization, crystal and molecular structure and theoretical study of N-(naphthalen-1-yl)-2-(piperidin-1-yl) acetamide, a selective butyrylcholinesterase inhibitor
dc.typeArticle


Este ítem pertenece a la siguiente institución