3α-Fluoro Analogues of "Allopregnanolone" and Their Binding to GABAA Receptors

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Title:3α-Fluoro Analogues of "Allopregnanolone" and Their Binding to GABAA Receptors
Creators:
Slavíková, Barbora
Kasal, Alexander
Chodounská, Hana
Krištofíková, Zdena
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 67, 1, pp. 30-46
Uncontrolled Keywords:<sup>1</sup>H NMR spectroscopy, Allopregnanolone, Neuroactive steroids, Fluorination, Fluorosteroids, Epalon

Abstract

(Diethylamino)sulfur trifluoride (DAST) was used for the preparation of 3α-fluorides (<i>e.g.</i>, 3α-fluoro-5α-pregnane-12,20-dione, 3α-fluoro-16α-[(methoxycarbonyl)methyl]-5α-pregnan-20-one, methyl 3α-fluoro-5α-androstane-17β-carboxylate, 3α-fluoro-5β-pregnan-20-one) from the corresponding 3β-alcohols and for the preparation of 3,3-difluorides from 3-ketones (<i>e.g.</i>, 3,3-difluoro-5α-pregnan-20-one). Boron trifluoride etherate was used for the conversion of an epoxide into 3α-fluoro-2β-hydroxy-5α-pregnan-20-one. The <i>in vitro</i> binding of the 3α-fluorides and the corresponding 3α-alcohols to the GABA<sub>A</sub> receptor was established using [<sup>3</sup>H]muscimol and [<sup>35</sup>S]-<i>tert</i>-butylbicyclo[2.2.2]phosphorothionate as ligands. <p>

Title:3α-Fluoro Analogues of "Allopregnanolone" and Their Binding to GABAA Receptors
Creators:
Slavíková, Barbora
Kasal, Alexander
Chodounská, Hana
Krištofíková, Zdena
Uncontrolled Keywords:<sup>1</sup>H NMR spectroscopy, Allopregnanolone, Neuroactive steroids, Fluorination, Fluorosteroids, Epalon
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:67
Number:1
Page Range:pp. 30-46
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20020030UNSPECIFIED
ID Code:1903
Item Type:Article
Deposited On:06 Feb 2009 17:13
Last Modified:06 Feb 2009 16:13

Citation

Slavíková, Barbora; Kasal, Alexander; Chodounská, Hana; Krištofíková, Zdena (2002) 3α-Fluoro Analogues of "Allopregnanolone" and Their Binding to GABAA Receptors. Collection of Czechoslovak Chemical Communications, 67 (1). pp. 30-46. ISSN 0010-0765

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