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Collect. Czech. Chem. Commun. 2002, 67, 30-46
https://doi.org/10.1135/cccc20020030

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

Barbora Slavíková*, Alexander Kasal, Hana Chodounská and Zdena Krištofíková

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic

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  • Cresswell Alexander J., Davies Stephen G., Roberts Paul M., Thomson James E.: Beyond the Balz–Schiemann Reaction: The Utility of Tetrafluoroborates and Boron Trifluoride as Nucleophilic Fluoride Sources. Chem. Rev. 2015, 115, 566. <https://doi.org/10.1021/cr5001805>
  • Slavikova Barbora, Kasal Alexander, Chodounska Hana, Kristofikova Zdena: ChemInform Abstract: Steroids. Part 413. 3α-Fluoro Analogues of “Allopregnanolone” and Their Binding to GABAA Receptors. ChemInform 2010, 33, no. <https://doi.org/10.1002/chin.200236186>
  • Dansey María V., Di Chenna Pablo H., Veleiro Adriana S., Krištofíková Zdena, Chodounska Hana, Kasal Alexander, Burton Gerardo: Synthesis and GABAA receptor activity of A-homo analogues of neuroactive steroids. Eur Med Chem 2010, 45, 3063. <https://doi.org/10.1016/j.ejmech.2010.03.037>
  • Durán Fernando J., Edelsztein Valeria C., Ghini Alberto A., Rey Mariana, Coirini Héctor, Dauban Philippe, Dodd Robert H., Burton Gerardo: Synthesis and GABAA receptor activity of 2,19-sulfamoyl analogues of allopregnanolone. Bioorganic & Medicinal Chemistry 2009, 17, 6526. <https://doi.org/10.1016/j.bmc.2009.08.008>
  • Slavíková Barbora, Krištofíková Zdena, Chodounská Hana, Buděšínský Miloš, Durán Fernando J., Veleiro Adriana S., Burton Gerardo, Kasal Alexander: Allopregnanolone (3α-Hydroxy-5α-pregnan-20-one) Derivatives with a Polar Chain in Position 16α: Synthesis and Activity. J. Med. Chem. 2009, 52, 2119. <https://doi.org/10.1021/jm801454a>
  • Eignerová Barbara, Slavíková Barbora, Buděšínský Miloš, Dračínský Martin, Klepetářová Blanka, Št’astná Eva, Kotora Martin: Synthesis of Fluorinated Brassinosteroids Based on Alkene Cross-Metathesis and Preliminary Biological Assessment. J. Med. Chem. 2009, 52, 5753. <https://doi.org/10.1021/jm900495f>
  • Herrmann Pavel, Kvíčala Jaroslav, Pouzar Vladimír, Chodounská Hana: Synthesis of Fluorinated Steroids Using a Novel Fluorinating Reagent Tetrabutylammonium Difluorodimethylphenylsilicate (TAMPS). Collect. Czech. Chem. Commun. 2008, 73, 1825. <https://doi.org/10.1135/cccc20081825>
  • Kasal Alexander, Krištofíková Zdena, Buděšínský Miloš: Neurosteroids: 7-aza-allopregnanolone—a poor substitute for allopregnanolone. Tetrahedron 2007, 63, 11355. <https://doi.org/10.1016/j.tet.2007.08.078>
  • Matyas Libor, Pohl Radek, Kasal Alexander: Neighboring Group Participation in 12,20-Dioxopregnanes. Natural Product Communications 2007, 2, 1934578X0700201. <https://doi.org/10.1177/1934578X0700201108>
  • Suñol Cristina, García Daniel A., Bujons Jordi, Krištofíková Zdena, Matyáš Libor, Babot Zoila, Kasal Alexander: Activity of B-Nor Analogues of Neurosteroids on the GABAA Receptor in Primary Neuronal Cultures. J. Med. Chem. 2006, 49, 3225. <https://doi.org/10.1021/jm060002f>
  • Kasal Alexander, Matyáš Libor, Buděšínský Miloš: Neurosteroid analogues: synthesis of 6-aza-allopregnanolone. Tetrahedron 2005, 61, 2269. <https://doi.org/10.1016/j.tet.2005.01.055>
  • Cyrański Michał K., Frelek Jadwiga, Jastrzębska Izabella, Morzycki Jacek W.: Rearrangement of 23-oxospirostanes to the 22-oxo-23-spiroketal isomers promoted by Lewis acids—X-ray crystal structure of (23R,25S)-3β-acetoxy-16β,23:23,26-diepoxy-5β-cholestan-22-one. Steroids 2004, 69, 395. <https://doi.org/10.1016/j.steroids.2004.03.010>
  • Matyáš Libor, Kasal Alexander, Babot Riera Zoila, Sunol Cristina E.: Effects of 3α-Amino-5α-pregnan-20-one on GABAA Receptor: Synthesis, Activity and Cytotoxicity. Collect. Czech. Chem. Commun. 2004, 69, 1506. <https://doi.org/10.1135/cccc20041506>
  • Reschel Miroslav, Buděšínský Miloš, Černý Ivan, Pouzar Vladimír, Drašar Pavel: Synthesis of Linear Steroid Oligoesters Based on Etienic Acid. Collect. Czech. Chem. Commun. 2002, 67, 1709. <https://doi.org/10.1135/cccc20021709>