About: Allopregnanolone and pregnanolone analogues modified in the C ring: synthesis and activity

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An Entity of Type : http://linked.opendata.cz/ontology/domain/vavai/Vysledek, within Data Space : linked.opendata.cz associated with source document(s)

Attributes	Values
rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
rdfs:seeAlso	http://pubs.acs.org/doi/pdf/10.1021/jm3016365
Description	(25R)-3 beta-Hydroxy-5 alpha-spirostan-12-one (hecogenin) and 11 alpha-hydroxypregn-4-ene-3,20-dione (11 alpha-hydroxyprogesterone) were used as starting materials for the synthesis of a series of 11- and 12-substituted derivatives of 5 xi-pregnanolone (3 alpha-hydroxy-5 alpha-pregnan-20-one and 3 alpha-hydroxy-5 beta-pregnan-20-one), the principal neurosteroid acting via gamma-aminobutyric acid (GABA). These analogues were designed to study the structural requirements of the corresponding GABA(A) receptor. Their biological activity was measured by in vitro test with [H-3]flunitrazepam as radio-ligand in which allopregnanolone and its active analogues stimulated the binding to the GABA(A) receptor. Analysis of the SAR data suggests dependence of the flunitrazepam binding activity on the hydrophobic-hydrophilic balance of the groups at the C-ring edge rather than on specific interactions between them and the receptor. (25R)-3 beta-Hydroxy-5 alpha-spirostan-12-one (hecogenin) and 11 alpha-hydroxypregn-4-ene-3,20-dione (11 alpha-hydroxyprogesterone) were used as starting materials for the synthesis of a series of 11- and 12-substituted derivatives of 5 xi-pregnanolone (3 alpha-hydroxy-5 alpha-pregnan-20-one and 3 alpha-hydroxy-5 beta-pregnan-20-one), the principal neurosteroid acting via gamma-aminobutyric acid (GABA). These analogues were designed to study the structural requirements of the corresponding GABA(A) receptor. Their biological activity was measured by in vitro test with [H-3]flunitrazepam as radio-ligand in which allopregnanolone and its active analogues stimulated the binding to the GABA(A) receptor. Analysis of the SAR data suggests dependence of the flunitrazepam binding activity on the hydrophobic-hydrophilic balance of the groups at the C-ring edge rather than on specific interactions between them and the receptor. (en)
Title	Allopregnanolone and pregnanolone analogues modified in the C ring: synthesis and activity Allopregnanolone and pregnanolone analogues modified in the C ring: synthesis and activity (en)
skos:prefLabel	Allopregnanolone and pregnanolone analogues modified in the C ring: synthesis and activity Allopregnanolone and pregnanolone analogues modified in the C ring: synthesis and activity (en)
skos:notation	RIV/00023752:_____/13:43914448!RIV14-MZ0-00023752
http://linked.open...avai/predkladatel	Psychiatrické centrum Praha
http://linked.open...avai/riv/aktivita	I P V
http://linked.open...avai/riv/aktivity	I, P(GAP303/12/1464), V
http://linked.open...iv/cisloPeriodika	6
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Krištofiková, Zdena
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Národní ústav duševního zdraví
http://linked.open...dnocenehoVysledku	60128
http://linked.open...ai/riv/idVysledku	RIV/00023752:_____/13:43914448
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	modulation; a receptors; analysis comsia; anesthetic steroids; neuroactive steroids; neurosteroid analogs; gaba(a) receptors; primary neuronal cultures; H-3 flunitrazepam binding; famma-aminobutyric-ACID (en)
http://linked.open.../riv/klicoveSlovo	neuroactive steroids H-3 flunitrazepam binding a receptors analysis comsia anesthetic steroids famma-aminobutyric-ACID gaba(a) receptors neurosteroid analogs primary neuronal cultures modulation
http://linked.open...odStatuVydavatele	US - Spojené státy americké
http://linked.open...ontrolniKodProRIV	[7B38BEDD805B]
http://linked.open...i/riv/nazevZdroje	Journal of Medicinal Chemistry
http://linked.open...in/vavai/riv/obor	FR
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	8 (xsd:int)
http://linked.open...vavai/riv/projekt	Neurosteroid modulation of NMDA receptors
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	56
http://linked.open...iv/tvurceVysledku	Kasal, Alexander Slavíková, Barbora Krištofiková, Zdena Babot, Zoila Bujons, Jordi Matyáš, Libor Sunol, Cristina Vidal, Miguel
http://linked.open...ain/vavai/riv/wos	000317032200013
issn	0022-2623
number of pages	14 (xsd:int)
http://bibframe.org/vocab/doi	10.1021/jm3016365

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