Synthesis and GABAA receptor activity of A-homo analogues of neuroactive steroids

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A procedure is described for the preparation of A-homo-5-pregnenes via an acid catalyzed rearrangement of cyclopropylcarbinols assisted by microwave irradiation. 3α-Hydroxy and 4α-hydroxy-A-homo-5- pregnen-20-one, analogues of the neuroactive steroid allopregnanolone, were obtained by means of a reg...

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Detalles Bibliográficos
Autor principal: Dansey, M.V
Otros Autores: Di Chenna, P.H, Veleiro, A.S, Krištofíková, Z., Chodounska, H., Kasal, A., Burton, G.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: Elsevier Masson SAS 2010
Acceso en línea:Registro en Scopus
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Aporte de:Registro referencial: Solicitar el recurso aquí
Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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024 7 |2 scopus  |a 2-s2.0-77954349521 
024 7 |2 cas  |a fructose, 30237-26-4, 57-48-7, 7660-25-5, 77907-44-9; sodium peroxide, 1313-60-6; tert butylbicyclophosphorothioate, 70636-86-1; hydroxide, 14280-30-9; Bicyclo Compounds, Heterocyclic; Hydroxides; Pregnenes; Receptors, GABA-A; hydroxide ion, 14280-30-9; tert-butylbicyclophosphorothionate, 70636-86-1 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a EJMCA 
100 1 |a Dansey, M.V. 
245 1 0 |a Synthesis and GABAA receptor activity of A-homo analogues of neuroactive steroids 
260 |b Elsevier Masson SAS  |c 2010 
270 1 0 |m Burton, G.; Departamento de Química Orgánica, UMYMFOR (CONICET-FCEN), Ciudad Universitaria, C1428EGA Buenos Aires, Argentina; email: burton@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
504 |a Belelli, D., Lambert, J., Neurosteroids: Endogenous regulators of the GABAA receptor (2005) Nat. Rev. Neurosci., 6, pp. 565-575 
504 |a Dubrosky, B.O., Steroids, neuroactive steroids and neurosteroids in psychopathology (2005) Prog. Neuro-Psychoph. Biol. Psyc., 29, pp. 169-192 
504 |a Akk, G., Covey, D.F., Evers, A.S., Steinbach, J.H., Zorumski, C.F., Mennerick, S., Mechanisms of neurosteroid interactions with GABAA receptors (2007) Pharmacol. Therapeut., 116, pp. 35-57 
504 |a Veleiro, A.S., Burton, G., Structureeactivity relationships of neuroactive steroids acting on the GABAA receptor (2009) Curr. Med. Chem., 16, pp. 455-472 
504 |a Covey, D.F., Hu, Y., Bouley, M.G., Holland, K.D., Rodgers-Neame, N.T., Isenberg, K.E., Zorumski, C.F., Modulation of GABAA receptor function by benz[e] indenes and phenanthrenes (1993) J. Med. Chem., 36, pp. 627-630 
504 |a Han, M., Hu, Y., Zorumski, Ch.F., Covey, D.F., Neurosteroid analogues. 3. the synthesis and electrophysiological evaluation of benz[e]indene congeners of neuroactive steroids having the 5β-configuration (1995) J. Med. Chem., 38, pp. 4548-4556 
504 |a Li, P., Covey, D.F., Steinbach, J.H., Akk, G., Dual potentiating and inhibitory actions of the benz[e]indene neurosteroid analog on recombinant α1β2γ2 GABAA receptor (2006) Mol. Pharmacol., 69, pp. 2015-2016 
504 |a Di Chenna, P.H., Dansey, M.V., Ghini, A.A., Burton, G., Rearrangement of 4b,5bmethylenepregnanes: A simple approach to A-homopregnanes and 5β methylpregnanes (2005) Arkivoc Xii, pp. 154-162 
504 |a Dan, Y., Ketone-catalyzed asymmetric epoxidation reactions (2004) Acc. Chem. Res., 37, pp. 497-505 
504 |a Annese, C., Daccolti, L., Dinoi, A., Fusco, C., Gandolfi, R., Curci, R., Concerning the reactivity of dioxiranes. Observations from experiments and theory (2008) J. Am. Chem. Soc., 130, pp. 1197-1204 
504 |a Bose, A.K., Hoffman, W.A., Manhas, M.S., Steroids., I.X., Facile inversion of unhindered sterol configuration (1973) Tetrahedron Lett., pp. 1619-1622 
504 |a Herr, J.R., A whirlwind tour of current Mitsunobu Chemistry (1999) Albany Molecular Research, Inc. Tech. Rep., 3, pp. 1-36 
504 |a Blunt, J.W., Stothers, J.B., 13C NMR Spectra of steroids-A survey and commentary (1977) Org. Magn. Res., 9, pp. 439-464 
504 |a Im, W.B., Blakeman, D.P., Correlation between gamma-aminobutyric acidA receptor ligand-induced changes in t-butylbicyclophosphoro [35S]thionate binding and 36Cl- uptake in rat cerebrocortical membranes (1991) Mol. Pharmacol., 39 
504 |a Wang, Z.-X., Tu, Y., Frohn, M., Zhang, J.-R., Shi, Y., An efficient catalytic asymmetric epoxidation method (1997) Journal of the American Chemical Society, 119 (46), pp. 11224-11235. , DOI 10.1021/ja972272g 
504 |a Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, Jr.J.A., Pople, J.A., (2003) GAUSSIAN 03, , Revision B.05. Gaussian, Inc., Pittsburgh, PA 
504 |a Slavíková, B., Kasal, A., Chodounská, H., Krístofíková, Z., 3a-Fluoro analogues of allopregnanolone and their binding to GABAA receptors (2002) Coll. Czech. Chem. Commun., 67, pp. 30-46 
520 3 |a A procedure is described for the preparation of A-homo-5-pregnenes via an acid catalyzed rearrangement of cyclopropylcarbinols assisted by microwave irradiation. 3α-Hydroxy and 4α-hydroxy-A-homo-5- pregnen-20-one, analogues of the neuroactive steroid allopregnanolone, were obtained by means of a regioselective epoxidation of a double bond in the expanded A-ring, using a fructose-derived chiral ketone as catalyst and oxone as oxidant. Although both these compounds were marginally active in inhibiting TBPS binding to GABA A receptors, 3β-hydroxy-A-homo-5-pregnen-20-one was almost as active as allopregnanolone. Reduction of the double bond of the latter compound resulted in a ten fold loss of activity. © 2010 Elsevier Masson SAS.  |l eng 
536 |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica, PICT-00727 
536 |a Detalles de la financiación: Universidad de Buenos Aires 
536 |a Detalles de la financiación: Grantová Agentura České Republiky, GACR203/08/1498, Z40550506 
536 |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas 
536 |a Detalles de la financiación: This work was supported by grants from Agencia Nacional de Promoción Científica y Tecnológica (PICT-00727), Universidad de Buenos Aires, CONICET (Argentina)-CSAV (Czech Republic) and Grant Agency of the Czech Republic (GACR203/08/1498 and Z40550506). 
593 |a Departamento de Química Orgánica, UMYMFOR (CONICET-FCEN), Ciudad Universitaria, C1428EGA Buenos Aires, Argentina 
593 |a Prague Psychiatric Centre, Ústavní 91, 181 03 Prague 8, Czech Republic 
593 |a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Fleming Square 2, CZ166 10 Prague 6, Czech Republic 
690 1 0 |a A-HOMOPREGNANE 
690 1 0 |a GABAA RECEPTOR 
690 1 0 |a NEUROSTEROID 
690 1 0 |a Γ-AMINOBUTYRIC ACID 
690 1 0 |a 3ALPHA HYDROXY 5ALPHA PREGNAN 20 ONE 
690 1 0 |a 3ALPHA HYDROXY A HOMO 5 PREGNEN 20 ONE 
690 1 0 |a 3BETA HYDROXY A HOMO 5 PREGNEN 20 ONE 
690 1 0 |a 3BETA HYDROXY A HOMO 5ALPHA H PREGNAN 20 ONE 
690 1 0 |a 4 AMINOBUTYRIC ACID A RECEPTOR 
690 1 0 |a 4ALPHA HYDROXY A HOMO 5 PREGNEN 20 ONE 
690 1 0 |a FRUCTOSE 
690 1 0 |a KETONE 
690 1 0 |a METHANOL DERIVATIVE 
690 1 0 |a NEUROACTIVE STEROID 
690 1 0 |a NEUROSTEROID 
690 1 0 |a OXIDIZING AGENT 
690 1 0 |a PREGNANE DERIVATIVE 
690 1 0 |a SODIUM PEROXIDE 
690 1 0 |a TERT BUTYLBICYCLOPHOSPHOROTHIOATE 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a 4 AMINOBUTYRIC ACID A RECEPTOR 
690 1 0 |a FUSED HETEROCYCLIC RINGS 
690 1 0 |a HYDROXIDE 
690 1 0 |a HYDROXIDE ION 
690 1 0 |a PREGNANE DERIVATIVE 
690 1 0 |a TERT BUTYLBICYCLOPHOSPHOROTHIOATE 
690 1 0 |a TERT-BUTYLBICYCLOPHOSPHOROTHIONATE 
690 1 0 |a ARTICLE 
690 1 0 |a BINDING AFFINITY 
690 1 0 |a CATALYSIS 
690 1 0 |a CATALYST 
690 1 0 |a CHEMICAL BOND 
690 1 0 |a CHIRALITY 
690 1 0 |a CONTROLLED STUDY 
690 1 0 |a DRUG CONFORMATION 
690 1 0 |a DRUG SYNTHESIS 
690 1 0 |a EPOXIDATION 
690 1 0 |a MICROWAVE IRRADIATION 
690 1 0 |a REACTION ANALYSIS 
690 1 0 |a RECEPTOR BINDING 
690 1 0 |a RING OPENING 
690 1 0 |a STEREOCHEMISTRY 
690 1 0 |a ANIMAL 
690 1 0 |a CHEMICAL STRUCTURE 
690 1 0 |a CHEMISTRY 
690 1 0 |a CONFORMATION 
690 1 0 |a DRUG EFFECT 
690 1 0 |a MALE 
690 1 0 |a METABOLISM 
690 1 0 |a MICROWAVE RADIATION 
690 1 0 |a PROTEIN BINDING 
690 1 0 |a RAT 
690 1 0 |a SYNTHESIS 
690 1 0 |a WISTAR RAT 
690 1 0 |a ANIMALS 
690 1 0 |a BICYCLO COMPOUNDS, HETEROCYCLIC 
690 1 0 |a HYDROXIDES 
690 1 0 |a MALE 
690 1 0 |a MICROWAVES 
690 1 0 |a MODELS, MOLECULAR 
690 1 0 |a MOLECULAR CONFORMATION 
690 1 0 |a PREGNENES 
690 1 0 |a PROTEIN BINDING 
690 1 0 |a RATS 
690 1 0 |a RATS, WISTAR 
690 1 0 |a RECEPTORS, GABA-A 
700 1 |a Di Chenna, P.H. 
700 1 |a Veleiro, A.S. 
700 1 |a Krištofíková, Z. 
700 1 |a Chodounska, H. 
700 1 |a Kasal, A. 
700 1 |a Burton, G. 
773 0 |d Elsevier Masson SAS, 2010  |g v. 45  |h pp. 3063-3069  |k n. 7  |p Eur. J. Med. Chem.  |x 02235234  |w (AR-BaUEN)CENRE-4668  |t European Journal of Medicinal Chemistry 
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856 4 0 |u https://doi.org/10.1016/j.ejmech.2010.03.037  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_02235234_v45_n7_p3063_Dansey  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02235234_v45_n7_p3063_Dansey  |y Registro en la Biblioteca Digital 
961 |a paper_02235234_v45_n7_p3063_Dansey  |b paper  |c PE 
962 |a info:eu-repo/semantics/article  |a info:ar-repo/semantics/artículo  |b info:eu-repo/semantics/publishedVersion 
999 |c 68729 

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