Wikipedia

Huprine Y

Huprine Y
Names
IUPAC name
7-chloro-15-methyl-10-azatetracyclo[11.3.1.02,11.04,9]heptadeca-2,4(9),5,7,10,14-hexaen-3-amine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C17H17ClN2/c1-9-4-10-6-11(5-9)16-15(7-10)20-14-8-12(18)2-3-13(14)17(16)19/h2-4,8,10-11H,5-7H2,1H3,(H2,19,20)
    Key: UKCBMHDZLYYTMI-UHFFFAOYSA-N
  • CC1=CC2CC(C1)C3=C(C4=C(C=C(C=C4)Cl)N=C3C2)N
Properties
C17H17ClN2
Molar mass 284.79 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Huprine Y is an anticholinesterase compound. According to research, it could potentially have usefulness in management of certain diseases such as Alzheimer's disease.[1][2]

Chemistry

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At the chemical level, huprine Y has a very similar structure to huprine X[3][4], another AChE inhibitor[5]. This chemical similarity could explain their similar mechanisms of action.

Mechanism of action

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As an anticholinesterase compound, its main mechanism of action is inhibition of the acetylcholine esterase enzyme, which hydrolyses acetylcholine[6]. In other words, Huprine Y reduces the action of the AChE enzyme, resulting in elevated levels of acetylcholine. Like other similar compounds, it appears to have strong affinity when binding to the enzyme.[7][8]

References

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  1. ^ Galdeano, Carles; Viayna, Elisabet; Sola, Irene; Formosa, Xavier; Camps, Pelayo; Badia, Albert; Clos, M. Victòria; Relat, Júlia; Ratia, Míriam; Bartolini, Manuela; Mancini, Francesca; Andrisano, Vincenza; Salmona, Mario; Minguillón, Cristina; González-Muñoz, Gema C. (2012-01-26). "Huprine-tacrine heterodimers as anti-amyloidogenic compounds of potential interest against Alzheimer's and prion diseases". Journal of Medicinal Chemistry. 55 (2): 661–669. doi:10.1021/jm200840c. ISSN 1520-4804. PMID 22185619.
  2. ^ Viayna, Elisabet; Coquelle, Nicolas; Cieslikiewicz-Bouet, Monika; Cisternas, Pedro; Oliva, Carolina A.; Sánchez-López, Elena; Ettcheto, Miren; Bartolini, Manuela; De Simone, Angela; Ricchini, Mattia; Rendina, Marisa; Pons, Mégane; Firuzi, Omidreza; Pérez, Belén; Saso, Luciano (2021-01-14). "Discovery of a Potent Dual Inhibitor of Acetylcholinesterase and Butyrylcholinesterase with Antioxidant Activity that Alleviates Alzheimer-like Pathology in Old APP/PS1 Mice". Journal of Medicinal Chemistry. 64 (1): 812–839. doi:10.1021/acs.jmedchem.0c01775. hdl:11585/790319. ISSN 1520-4804. PMID 33356266.
  3. ^ PubChem. "Huprine Y". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-07-29.
  4. ^ PubChem. "Huprine X". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-07-29.
  5. ^ Camps, P.; Cusack, B.; Mallender, W. D.; El Achab, R. E.; Morral, J.; Muñoz-Torrero, D.; Rosenberry, T. L. (February 2000). "Huprine X is a novel high-affinity inhibitor of acetylcholinesterase that is of interest for treatment of Alzheimer's disease". Molecular Pharmacology. 57 (2): 409–417. doi:10.1016/S0026-895X(24)23214-4. ISSN 0026-895X. PMID 10648652.
  6. ^ Dvir, Hay; Silman, Israel; Harel, Michal; Rosenberry, Terrone L.; Sussman, Joel L. (2010-09-06). "Acetylcholinesterase: from 3D structure to function". Chemico-Biological Interactions. 187 (1–3): 10–22. Bibcode:2010CBI...187...10D. doi:10.1016/j.cbi.2010.01.042. ISSN 1872-7786. PMC 2894301. PMID 20138030.
  7. ^ Camps, Pelayo; Formosa, Xavier; Muñoz-Torrero, Diego; Petrignet, Julien; Badia, Albert; Clos, M. Victoria (2005-03-24). "Synthesis and pharmacological evaluation of huprine-tacrine heterodimers: subnanomolar dual binding site acetylcholinesterase inhibitors". Journal of Medicinal Chemistry. 48 (6): 1701–1704. doi:10.1021/jm0496741. ISSN 0022-2623. PMID 15771413.
  8. ^ Ronco, Cyril; Carletti, Eugénie; Colletier, Jacques-Philippe; Weik, Martin; Nachon, Florian; Jean, Ludovic; Renard, Pierre-Yves (2012). "Huprine Derivatives as Sub-Nanomolar Human Acetylcholinesterase Inhibitors: From Rational Design to Validation by X-ray Crystallography". ChemMedChem. 7 (3): 400–405. doi:10.1002/cmdc.201100438. ISSN 1860-7187. PMID 22052791.