Synthesis of deuterium labeled NMDA receptor inhibitor-20-Oxo-5 beta-[9,12,12-H-2(3)]pregnan-3 alpha-yl-L-glutamyl 1-ester

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F12%3A10132876" target="_blank" >RIV/00216208:11310/12:10132876 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/67985823:_____/12:00376383 RIV/61989592:15310/12:33143005 RIV/61388963:_____/12:00376383

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.steroids.2011.12.019" target="_blank" >http://dx.doi.org/10.1016/j.steroids.2011.12.019</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.steroids.2011.12.019" target="_blank" >10.1016/j.steroids.2011.12.019</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of deuterium labeled NMDA receptor inhibitor-20-Oxo-5 beta-[9,12,12-H-2(3)]pregnan-3 alpha-yl-L-glutamyl 1-ester

Popis výsledku v původním jazyce

20-Oxo-5 beta-[9,12,12-H-2(3)]pregnan-3 alpha-yl-L-glutamyl 1-ester 11 was synthesized as an internal standard for quantification of a neuroprotective NMDA receptor ligand, 20-oxo-5 beta-pregnan-3 alpha-yl-L-glutamyl 1-ester 18 and its metabolites, in plasma and tissue. 11 alpha-Hydroxy-progesterone (1) was reduced under basic conditions to yield the corresponding 5 beta-steroid. Protection of the 3- and 20-oxo groups and oxidation of the 11 alpha-hydroxy group was then followed by a deuterium exchange,conducted under basic conditions using deuterated methanol. Next, the carbonyl moiety at C-11 was reduced and the 11 alpha-hydroxyl group removed through utilization of the Barton-McCombie reaction. Subsequent deprotection of the 3- and 20-acetals and stereoselective reduction of the 3-oxo group gave the desired trideuterated pregnanolone (8). This was coupled with protected glutamic acid, which was then deprotected to yield [9,12,12-H-2(3)]-pregnanolone glutamate (11) with >99% isotopi

Název v anglickém jazyce

Synthesis of deuterium labeled NMDA receptor inhibitor-20-Oxo-5 beta-[9,12,12-H-2(3)]pregnan-3 alpha-yl-L-glutamyl 1-ester

Popis výsledku anglicky

20-Oxo-5 beta-[9,12,12-H-2(3)]pregnan-3 alpha-yl-L-glutamyl 1-ester 11 was synthesized as an internal standard for quantification of a neuroprotective NMDA receptor ligand, 20-oxo-5 beta-pregnan-3 alpha-yl-L-glutamyl 1-ester 18 and its metabolites, in plasma and tissue. 11 alpha-Hydroxy-progesterone (1) was reduced under basic conditions to yield the corresponding 5 beta-steroid. Protection of the 3- and 20-oxo groups and oxidation of the 11 alpha-hydroxy group was then followed by a deuterium exchange,conducted under basic conditions using deuterated methanol. Next, the carbonyl moiety at C-11 was reduced and the 11 alpha-hydroxyl group removed through utilization of the Barton-McCombie reaction. Subsequent deprotection of the 3- and 20-acetals and stereoselective reduction of the 3-oxo group gave the desired trideuterated pregnanolone (8). This was coupled with protected glutamic acid, which was then deprotected to yield [9,12,12-H-2(3)]-pregnanolone glutamate (11) with >99% isotopi

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2012

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Steroids

ISSN

0039-128X

e-ISSN

—

Svazek periodika

77

Číslo periodika v rámci svazku

3

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

6

Strana od-do

282-287

Kód UT WoS článku

000300523000015

EID výsledku v databázi Scopus

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