- -

Multisite organic-inorganic hybrid catalysts for the direct sustainable synthesis of GABAergic drugs

RiuNet: Repositorio Institucional de la Universidad Politécnica de Valencia

Compartir/Enviar a

Citas

Estadísticas

  • Estadisticas de Uso

Multisite organic-inorganic hybrid catalysts for the direct sustainable synthesis of GABAergic drugs

Mostrar el registro sencillo del ítem

Ficheros en el ítem

dc.contributor.author Leyva Perez, Antonio es_ES
dc.contributor.author García García, Pilar es_ES
dc.contributor.author Corma Canós, Avelino es_ES
dc.date.accessioned 2016-01-18T09:31:45Z
dc.date.issued 2014-08-11
dc.identifier.issn 1433-7851
dc.identifier.uri http://hdl.handle.net/10251/59969
dc.description.abstract Multisite organic inorganic hybrid catalysts have been prepared and applied in a new general, practical, and sustainable synthetic procedure toward industrially relevant GABA derivatives. The domino sequence is composed of seven chemical transformations which are performed in two one-pot reactions. The method produces both enantiomeric forms of the product in high enantiopurity as well as the racemate in good yields after a single column purification step. This protocol highlights major process intensification, catalyst recyclability, and low waste generation. es_ES
dc.description.sponsorship This work was supported by the Spanish Government (Consolider Ingenio 2010-MULTICAT (CSD2009-00050) and MAT2011-29020-C02-01). P.G.-G. is grateful for a JAE-DOC contract from CSIC cofunded by the ESF. A.L.P. thanks ITQ for a contract. The Severo Ochoa program is thankfully acknowledged. en_EN
dc.language Inglés es_ES
dc.publisher Wiley-VCH Verlag es_ES
dc.relation.ispartof Angewandte Chemie International Edition es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject gamma-aminobutyric acid es_ES
dc.subject domino reactions es_ES
dc.subject GABAergic drug synthesis es_ES
dc.subject heterogeneous catalysis es_ES
dc.subject organic-inorganic hybrid catalysts es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Multisite organic-inorganic hybrid catalysts for the direct sustainable synthesis of GABAergic drugs es_ES
dc.type Artículo es_ES
dc.embargo.lift 10000-01-01
dc.embargo.terms forever es_ES
dc.identifier.doi 10.1002/anie.201403049
dc.relation.projectID info:eu-repo/grantAgreement/MICINN//CSD2009-00050/ES/Desarrollo de catalizadores más eficientes para el diseño de procesos químicos sostenibles y produccion limpia de energia/ es_ES
dc.rights.accessRights Cerrado es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.description.bibliographicCitation Leyva Perez, A.; García García, P.; Corma Canós, A. (2014). Multisite organic-inorganic hybrid catalysts for the direct sustainable synthesis of GABAergic drugs. Angewandte Chemie International Edition. 53(33):8687-8690. https://doi.org/10.1002/anie.201403049 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://dx.doi.org/10.1002/anie.201403049 es_ES
dc.description.upvformatpinicio 8687 es_ES
dc.description.upvformatpfin 8690 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 53 es_ES
dc.description.issue 33 es_ES
dc.relation.senia 282347 es_ES
dc.identifier.eissn 1521-3773
dc.contributor.funder Ministerio de Ciencia e Innovación es_ES
dc.description.references Sanchez, C., Julián, B., Belleville, P., & Popall, M. (2005). Applications of hybrid organic–inorganic nanocomposites. Journal of Materials Chemistry, 15(35-36), 3559. doi:10.1039/b509097k es_ES
dc.description.references Margelefsky, E. L., Zeidan, R. K., & Davis, M. E. (2008). Cooperative catalysis by silica-supported organic functional groups. Chemical Society Reviews, 37(6), 1118. doi:10.1039/b710334b es_ES
dc.description.references CLIMENT, M., CORMA, A., IBORRA, S., & MIFSUD, M. (2007). MgO nanoparticle-based multifunctional catalysts in the cascade reaction allows the green synthesis of anti-inflammatory agents. Journal of Catalysis, 247(2), 223-230. doi:10.1016/j.jcat.2007.02.003 es_ES
dc.description.references Notestein, J. M., & Katz, A. (2006). Enhancing Heterogeneous Catalysis through Cooperative Hybrid Organic–Inorganic Interfaces. Chemistry - A European Journal, 12(15), 3954-3965. doi:10.1002/chem.200501152 es_ES
dc.description.references Díaz, U., Brunel, D., & Corma, A. (2013). Catalysis using multifunctional organosiliceous hybrid materials. Chemical Society Reviews, 42(9), 4083. doi:10.1039/c2cs35385g es_ES
dc.description.references Westermann, B., Ayaz, M., & van Berkel, S. S. (2010). Enantiodivergente Organokaskadenreaktionen. Angewandte Chemie, 122(5), 858-861. doi:10.1002/ange.200904638 es_ES
dc.description.references Westermann, B., Ayaz, M., & van Berkel, S. S. (2009). Enantiodivergent Organocascade Reactions. Angewandte Chemie International Edition, 49(5), 846-849. doi:10.1002/anie.200904638 es_ES
dc.description.references Nicolaou, K. C., Edmonds, D. J., & Bulger, P. G. (2006). Kaskadenreaktionen in der Totalsynthese. Angewandte Chemie, 118(43), 7292-7344. doi:10.1002/ange.200601872 es_ES
dc.description.references Nicolaou, K. C., Edmonds, D. J., & Bulger, P. G. (2006). Cascade Reactions in Total Synthesis. Angewandte Chemie International Edition, 45(43), 7134-7186. doi:10.1002/anie.200601872 es_ES
dc.description.references Grossmann, A., & Enders, D. (2011). Durch N-heterocyclische Carbene katalysierte Dominoreaktionen. Angewandte Chemie, 124(2), 320-332. doi:10.1002/ange.201105415 es_ES
dc.description.references Grossmann, A., & Enders, D. (2011). N-Heterocyclic Carbene Catalyzed Domino Reactions. Angewandte Chemie International Edition, 51(2), 314-325. doi:10.1002/anie.201105415 es_ES
dc.description.references Friedman, A. A., Panteleev, J., Tsoung, J., Huynh, V., & Lautens, M. (2013). Rh/Pd Catalysis with Chiral and Achiral Ligands: Domino Synthesis of Aza-Dihydrodibenzoxepines. Angewandte Chemie, 125(37), 9937-9940. doi:10.1002/ange.201303659 es_ES
dc.description.references Friedman, A. A., Panteleev, J., Tsoung, J., Huynh, V., & Lautens, M. (2013). Rh/Pd Catalysis with Chiral and Achiral Ligands: Domino Synthesis of Aza-Dihydrodibenzoxepines. Angewandte Chemie International Edition, 52(37), 9755-9758. doi:10.1002/anie.201303659 es_ES
dc.description.references Watanabe, M., Maemura, K., Kanbara, K., Tamayama, T., & Hayasaki, H. (2002). GABA and GABA Receptors in the Central Nervous System and Other Organs. A Survey of Cell Biology, 1-47. doi:10.1016/s0074-7696(02)13011-7 es_ES
dc.description.references Ting Wong, C. G., Bottiglieri, T., & Snead, O. C. (2003). GABA, ?-hydroxybutyric acid, and neurological disease. Annals of Neurology, 54(S6), S3-S12. doi:10.1002/ana.10696 es_ES
dc.description.references Simpson, M. D. ., Slater, P., & Deakin, J. F. . (1998). Comparison of glutamate and gamma-aminobutyric acid uptake binding sites in frontal and temporal lobes in schizophrenia. Biological Psychiatry, 44(6), 423-427. doi:10.1016/s0006-3223(98)00077-8 es_ES
dc.description.references Pearl, P. L., Hartka, T. R., Cabalza, J. L., Taylor, J., & Gibson, M. K. (2006). Inherited disorders of GABA metabolism. Future Neurology, 1(5), 631-636. doi:10.2217/14796708.1.5.631 es_ES
dc.description.references N’Goka, V., Schlewer, G., Linget, J. M., Chambon, J. P., & Wermuth, C. G. (1991). GABA-uptake inhibitors: construction of a general pharmacophore model and successful prediction of a new representative. Journal of Medicinal Chemistry, 34(8), 2547-2557. doi:10.1021/jm00112a032 es_ES
dc.description.references Gajcy, K., Lochynski, S., & Librowski, T. (2010). A Role of GABA Analogues in the Treatment of Neurological Diseases. Current Medicinal Chemistry, 17(22), 2338-2347. doi:10.2174/092986710791698549 es_ES
dc.description.references Olpe, H.-R., Demiéville, H., Baltzer, V., Bencze, W. L., Koella, W. P., Wolf, P., & Haas, H. L. (1978). The biological activity of d-baclofen (Lipresal®). European Journal of Pharmacology, 52(1), 133-136. doi:10.1016/0014-2999(78)90032-8 es_ES
dc.description.references Lapin, I. (2006). Phenibut (β-Phenyl-GABA): A Tranquilizer and Nootropic Drug. CNS Drug Reviews, 7(4), 471-481. doi:10.1111/j.1527-3458.2001.tb00211.x es_ES
dc.description.references Kanes, S. J., Tokarczyk, J., Siegel, S. J., Bilker, W., Abel, T., & Kelly, M. P. (2007). Rolipram: A specific phosphodiesterase 4 inhibitor with potential antipsychotic activity. Neuroscience, 144(1), 239-246. doi:10.1016/j.neuroscience.2006.09.026 es_ES
dc.description.references Chen, R.-W., Williams, A. J., Liao, Z., Yao, C., Tortella, F. C., & Dave, J. R. (2007). Broad spectrum neuroprotection profile of phosphodiesterase inhibitors as related to modulation of cell-cycle elements and caspase-3 activation. Neuroscience Letters, 418(2), 165-169. doi:10.1016/j.neulet.2007.03.033 es_ES
dc.description.references Smith, D. L., Pozueta, J., Gong, B., Arancio, O., & Shelanski, M. (2009). Reversal of long-term dendritic spine alterations in Alzheimer disease models. Proceedings of the National Academy of Sciences, 106(39), 16877-16882. doi:10.1073/pnas.0908706106 es_ES
dc.description.references Wachtel, H. (1983). Potential antidepressant activity of rolipram and other selective cyclic adenosine 3′,5′-monophosphate phosphodiesterase inhibitors. Neuropharmacology, 22(3), 267-272. doi:10.1016/0028-3908(83)90239-3 es_ES
dc.description.references Nibuya, M., Nestler, E., & Duman, R. (1996). Chronic antidepressant administration increases the expression of cAMP response element binding protein (CREB) in rat hippocampus. The Journal of Neuroscience, 16(7), 2365-2372. doi:10.1523/jneurosci.16-07-02365.1996 es_ES
dc.description.references Bowery, N. G., Hill, D. R., Hudson, A. L., Doble, A., Middlemiss, D. N., Shaw, J., & Turnbull, M. (1980). (–)Baclofen decreases neurotransmitter release in the mammalian CNS by an action at a novel GABA receptor. Nature, 283(5742), 92-94. doi:10.1038/283092a0 es_ES
dc.description.references Mann, A., Boulanger, T., Brandau, B., Durant, F., Evrard, G., Heaulme, M., … Wermuth, C. G. (1991). Synthesis and biochemical evaluation of baclofen analogs locked in the baclofen solid-state conformation. Journal of Medicinal Chemistry, 34(4), 1307-1313. doi:10.1021/jm00108a011 es_ES
dc.description.references Belliotti, T. R., Capiris, T., Ekhato, I. V., Kinsora, J. J., Field, M. J., Heffner, T. G., … Wustrow, D. J. (2005). Structure−Activity Relationships of Pregabalin and Analogues That Target the α2-δ Protein. Journal of Medicinal Chemistry, 48(7), 2294-2307. doi:10.1021/jm049762l es_ES
dc.description.references Hynes, P. S., Stupple, P. A., & Dixon, D. J. (2008). Organocatalytic Asymmetric Total Synthesis of (R)-Rolipram and Formal Synthesis of (3S,4R)-Paroxetine. Organic Letters, 10(7), 1389-1391. doi:10.1021/ol800108u es_ES
dc.description.references Poe, S. L., Kobašlija, M., & McQuade, D. T. (2007). Mechanism and Application of a Microcapsule Enabled Multicatalyst Reaction. Journal of the American Chemical Society, 129(29), 9216-9221. doi:10.1021/ja071706x es_ES
dc.description.references Barnes, D. M., Ji, J., Fickes, M. G., Fitzgerald, M. A., King, S. A., Morton, H. E., … Zhang, J. (2002). Development of a Catalytic Enantioselective Conjugate Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes for the Synthesis of Endothelin-A AntagonistABT-546. Scope, Mechanism, and Further Application to the Synthesis of the Antidepressant Rolipram. Journal of the American Chemical Society, 124(44), 13097-13105. doi:10.1021/ja026788y es_ES
dc.description.references Palomo, C., Landa, A., Mielgo, A., Oiarbide, M., Puente, Á., & Vera, S. (2007). Water-Compatible Iminium Activation: Organocatalytic Michael Reactions of Carbon-Centered Nucleophiles with Enals. Angewandte Chemie, 119(44), 8583-8587. doi:10.1002/ange.200703261 es_ES
dc.description.references Palomo, C., Landa, A., Mielgo, A., Oiarbide, M., Puente, Á., & Vera, S. (2007). Water-Compatible Iminium Activation: Organocatalytic Michael Reactions of Carbon-Centered Nucleophiles with Enals. Angewandte Chemie International Edition, 46(44), 8431-8435. doi:10.1002/anie.200703261 es_ES
dc.description.references Furutachi, M., Mouri, S., Matsunaga, S., & Shibasaki, M. (2010). A Heterobimetallic Ni/La-salan Complex for Catalytic Asymmetric Decarboxylative 1,4-Addition of Malonic Acid Half-Thioester. Chemistry - An Asian Journal, 5(11), 2351-2354. doi:10.1002/asia.201000540 es_ES
dc.description.references Bassas, O., Huuskonen, J., Rissanen, K., & Koskinen, A. M. P. (2009). A Simple Organocatalytic Enantioselective Synthesis of Pregabalin. European Journal of Organic Chemistry, 2009(9), 1340-1351. doi:10.1002/ejoc.200801220 es_ES
dc.description.references Liu, J., Wang, X., Ge, Z., Sun, Q., Cheng, T., & Li, R. (2011). Solvent-free organocatalytic Michael addition of diethyl malonate to nitroalkenes: the practical synthesis of Pregabalin and γ-nitrobutyric acid derivatives. Tetrahedron, 67(3), 636-640. doi:10.1016/j.tet.2010.11.053 es_ES
dc.description.references Chen, Z., Chen, Z., Jiang, Y., & Hu, W. (2005). The synthesis of baclofen and GABOB via Rh(II) catalyzed intramolecular C–H insertion of α-diazoacetamides. Tetrahedron, 61(6), 1579-1586. doi:10.1016/j.tet.2004.11.077 es_ES
dc.description.references Okino, T., Hoashi, Y., Furukawa, T., Xu, X., & Takemoto, Y. (2005). Enantio- and Diastereoselective Michael Reaction of 1,3-Dicarbonyl Compounds to Nitroolefins Catalyzed by a Bifunctional Thiourea. Journal of the American Chemical Society, 127(1), 119-125. doi:10.1021/ja044370p es_ES
dc.description.references Sheldon, R. A. (2007). The E Factor: fifteen years on. Green Chemistry, 9(12), 1273. doi:10.1039/b713736m es_ES
dc.description.references García-García, P., Zagdoun, A., Copéret, C., Lesage, A., Díaz, U., & Corma, A. (2013). In situ preparation of a multifunctional chiral hybrid organic–inorganic catalyst for asymmetric multicomponent reactions. Chemical Science, 4(5), 2006. doi:10.1039/c3sc22310h es_ES
dc.description.references Pastre, J. C., Browne, D. L., & Ley, S. V. (2013). Flow chemistry syntheses of natural products. Chemical Society Reviews, 42(23), 8849. doi:10.1039/c3cs60246j es_ES


Este ítem aparece en la(s) siguiente(s) colección(ones)

Mostrar el registro sencillo del ítem