Collect. Czech. Chem. Commun. 2000, 65, 1754-1761
https://doi.org/10.1135/cccc20001754

Synthesis of (20S)-2α,3α-Dihydroxy-6-oxo-7-oxa-7a-homo-5α-pregnane-20-carboxylic Acid as a Brassinosteroid Part of Ligands for Binding to Affinity Chromatography Carriers

Ladislav Kohouta,*, Hana Chodounskáa, Tomáš Maceka and Miroslav Strnadb

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, CZ-166 10 Prague 6, Czech Republic
b Laboratory of Growth Regulators, Institute of Experimental Botany, Academy of Sciences of the Czech Republic and Faculty of Natural Sciences of Palacký University, Šlechtitelů 11, CZ-783 71 Olomouc, Czech Republic

Individual author index pages


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  • Terezie Urbanová, Danuše Tarkowská*, Miroslav Strnad and Peter Hedden
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    2011, Vol. 76, Issue 12, pp. 1669–1686 [Abstract]
  • Eva Šťastná, Hana Chodounská*, Vladimír Pouzar, Jiřina Borovská and Ladislav Vyklický, Jr.
    Synthesis of pregnane 3-carboxylic acids via Pd-catalyzed alkoxycarbonylation and their effect on NMDA receptor activity
    2011, Vol. 76, Issue 9, pp. 1141–1161 [Abstract]
  • Vojtěch Kapras, Eva Šťastná, Hana Chodounská*, Vladimír Pouzar and Zdena Krištofíková
    Preparation of steroid sulfamates and their interaction with GABAA receptor
    2009, Vol. 74, Issue 4, pp. 643–650 [Abstract]
  • Pavel Herrmann, Jaroslav Kvíčala, Vladimír Pouzar and Hana Chodounská*
    Synthesis of Fluorinated Steroids Using a Novel Fluorinating Reagent Tetrabutylammonium Difluorodimethylphenylsilicate (TAMPS)
    2008, Vol. 73, Issue 12, pp. 1825–1834 [Abstract]
  • František Franěk*, Tomáš Eckschlager and Ladislav Kohout
    24-Epibrassinolide at Subnanomolar Concentrations Modulates Growth and Production Characteristics of a Mouse Hybridoma
    2003, Vol. 68, Issue 11, pp. 2190–2200 [Abstract]
  • Miroslav Šíša, Miloš Buděšínský and Ladislav Kohout*
    Synthesis and Biological Activity of 7a-Homo- and 7a,7b-Dihomo-5α-cholestane Analogues of Brassinolide
    2003, Vol. 68, Issue 11, pp. 2171–2189 [Abstract]
  • František Franěk*, Věra Siglerová, Libor Havlíček, Miroslav Strnad, Tomáš Eckschlager and Evžen Weigl
    Effect of the Purine Derivative Myoseverin and of Its Analogues on Cultured Hybridoma Cells
    2002, Vol. 67, Issue 2, pp. 257–266 [Abstract]
  • Barbora Slavíková*, Alexander Kasal, Hana Chodounská and Zdena Krištofíková
    3α-Fluoro Analogues of "Allopregnanolone" and Their Binding to GABAA Receptors
    2002, Vol. 67, Issue 1, pp. 30–46 [Abstract]
  • Hana Chodounská, Miloš Buděšínský, Romana Šídová, Miroslav Šíša, Alexander Kasal and Ladislav Kohout*
    Simple NMR Determination of 5α/5β Configuration of 3-Oxosteroids
    2001, Vol. 66, Issue 10, pp. 1529–1544 [Abstract]
  • Hana Chodounská* and Alexander Kasal
    Allopregnanolone Derivatives: Synthesis of 3α-Hydroxy-7a-homo-5α-pregnan-20-one
    2000, Vol. 65, Issue 7, pp. 1156–1162 [Abstract]
  • Jaroslava Hniličková* and Ladislav Kohout
    Synthesis of 21-Hydroxy-6β,19-epoxypregn-4-ene-3,20-dione
    2000, Vol. 65, Issue 3, pp. 380–384 [Abstract]
  • Petra Kučerová, Martina Macková*, Ludmila Poláchová, Jiří Burkhard, Kateřina Demnerová, Jarmila Pazlarová and Tomáš Macek
    Correlation of PCB Transformation by Plant Tissue Cultures with Their Morphology and Peroxidase Activity Changes
    1999, Vol. 64, Issue 9, pp. 1497–1509 [Abstract]
  • Pavel Kotrba, Tomáš Macek and Tomáš Ruml*
    Heavy Metal-Binding Peptides and Proteins in Plants. A Review
    1999, Vol. 64, Issue 7, pp. 1057–1086 [Abstract]
  • Carme Brosa, Ismael Zamora, Emma Terricabras and Ladislav Kohout
    The Effect of Electrostatic Properties and Abibility to Form Hydrogen-Bonds on the Activity of Brassinosteroid Side-Chain Analogs
    1998, Vol. 63, Issue 10, pp. 1635–1645 [Abstract]
  • Hana Chodounská and Alexander Kasal
    Epalons: Synthesis of 3α,7α-Dihydroxy-5α-pregnan-20-one
    1998, Vol. 63, Issue 10, pp. 1543–1548 [Abstract]
  • Romana Šídová, Karel Stránský, Alexander Kasal, Barbora Slavíková and Ladislav Kohout
    Long-Range Effect of 17-Substituents in 3-Oxo Steroids on 4,5-Double Bond Hydrogenation
    1998, Vol. 63, Issue 10, pp. 1528–1542 [Abstract]
  • Barbora Slavíková, Alexander Kasal and Ladislav Kohout
    N-Benzoyl-N-methylandrostan-17β-amines; 20-Aza Analogues of Brassinolide
    1998, Vol. 63, Issue 5, pp. 655–661 [Abstract]
  • Ladislav Kohout, Barbora Slavíková and Miroslav Strnad
    17a-Oxa-17a-homobrassinosteroid Analogues
    1998, Vol. 63, Issue 5, pp. 646–654 [Abstract]
  • Lucie Dalibová and Ladislav Kohout
    Preparation of Steroid Olefins from Heptafluorobutyrates
    1998, Vol. 63, Issue 4, pp. 549–556 [Abstract]
  • Alexander Kasal, Barbora Slavíková, Ladislav Kohout and Miloš Buděšínský
    The Synthesis of A-Homo-B-norandrostanes: The Effect of a Hydroxyl on the Course of Hydrogenation of the ∆9-Double Bond
    1997, Vol. 62, Issue 10, pp. 1631–1641 [Abstract]
  • Alexander Kasal, Hana Chodounská and Wojciech J. Szczepek
    trans-Hydrindanes by Reduction: Synthesis of Dihydro-B-nortestosterone
    1996, Vol. 61, Issue 9, pp. 1386–1395 [Abstract]
  • Hana Chodounská, Alexander Kasal, David Šaman and Karel Ubik
    One-Pot Deuteration and Reduction of Ketones in the Synthesis of [16,16,17-2H3]-Epitestosterone
    1996, Vol. 61, Issue 7, pp. 1037–1046 [Abstract]
  • Ladislav Kohout, Alexander Kasal and Miroslav Strnad
    Pregnane-Type Brassinosteroids with a Four-Carbon Ester Functionality in Position 20
    1996, Vol. 61, Issue 6, pp. 930–940 [Abstract]
  • Alexander Kasal, Ladislav Kohout and Michal Lebl
    Synthesis of a Scaffold for the Creation of Non-Peptide Libraries
    1995, Vol. 60, Issue 12, pp. 2147–2155 [Abstract]
  • Ladislav Kohout
    7-Oxo-7a-oxa-brassinosteroids with Cholestane Side-Chain
    1994, Vol. 59, Issue 5, pp. 1219–1225 [Abstract]
  • Ladislav Kohout and Alexander Kasal
    7a-Keto-B-homotestosterone and 7a-Keto-B-homoepitestosterone
    1994, Vol. 59, Issue 3, pp. 649–657 [Abstract]
  • Ladislav Kohout
    New Method of Preparation of Brassinosteroids
    1994, Vol. 59, Issue 2, pp. 457–460 [Abstract]
  • Hana Chodounská, Barbora Slavíková and Alexander Kasal
    Synthesis of Some Epitestosterone Analogues
    1994, Vol. 59, Issue 2, pp. 435–443 [Abstract]
  • Hana Chodounská and Vladimír Pouzar
    Preparation of 3-(6-Deoxy-β-D-glucopyranosyloxy) and 3-(6-Deoxy-α-L-mannopyranosyloxy)androstane Derivatives with Unsaturated Side Chain in Position 17β
    1993, Vol. 58, Issue 12, pp. 3000–3008 [Abstract]
  • Alexander Kasal, Richard Hampl, Zdeněk Putz, Ladislav Kohout and Luboslav Stárka
    Preparation and Properties of Three Immunogens with a Spacer on the β-Side of the Steroid Skeleton and the Effect of Immunogen Structure on Specificity of the Obtained Antisera
    1992, Vol. 57, Issue 10, pp. 2166–2173 [Abstract]
  • Ladislav Kohout and Miroslav Strnad
    Brassinosteroids with Ester Function with Five Carbon Atoms at the 20 Position
    1992, Vol. 57, Issue 8, pp. 1731–1738 [Abstract]
  • Vladimír Pouzar, Hana Chodounská, Ivan Černý and Pavel Drašar
    Derivatives of 5α-androstan-3α- and 3β-ol with acrylonitrile side chain
    1991, Vol. 56, Issue 12, pp. 2906–2916 [Abstract]
  • Hana Chodounská and Vladimír Pouzar
    Preparation of 3-(β-D-galactopyranosyloxy)androstane derivatives with unsaturated side chain in position 17β
    1990, Vol. 55, Issue 6, pp. 1639–1646 [Abstract]
  • Vladimír Pouzar, Hana Chodounská, Dalibor Sameš, Pavel Drašar and Miroslav Havel
    Derivatives of 5α-androstan-3α- and 3β-ol with acrylate side chain
    1990, Vol. 55, Issue 5, pp. 1243–1256 [Abstract]
  • Ladislav Kohout
    Syntheis of brassino steroids with a five carbon atom ester functionality in position 17
    1989, Vol. 54, Issue 12, pp. 3348–3359 [Abstract]
  • Ladislav Kohout
    7-Methanesulfonyloxy-3α,5-cyclo-5α-cholestanes
    1989, Vol. 54, Issue 4, pp. 1028–1035 [Abstract]
  • Ladislav Kohout and Miroslav Strnad
    Brassinolide analogues without side chain
    1989, Vol. 54, Issue 4, pp. 1019–1027 [Abstract]
  • Eva Klinotová, Helena Pavlíková, Martina Pressová, Hana Chodounská, Jiří Klinot, Jiří Protiva and Alois Vystrčil
    E-seco-Acids of pentacyclic triterpenoids. Oxidative cleavage of ring E in 3β-acetoxy-21-oxo-18α,19βH-ursan-28→20β-olide
    1987, Vol. 52, Issue 11, pp. 2744–2752 [Abstract]
  • Zdeněk Wimmer, Miloš Buděšínský, Tomáš Macek, Aleš Svatoš, David Šaman, Soňa Vašíčková and Miroslav Romaňuk
    Biotransformation of 2-(4-methoxybenzyl)-1-cyclohexanone by means of Saccharomyces cerevisiae
    1987, Vol. 52, Issue 9, pp. 2326–2337 [Abstract]
  • Ladislav Kohout, Václav Černý and Miroslav Strnad
    Alternative syntheses of 2α,3α,17β-trihydroxy-7-oxa-B-homo-5α-androstan-6-one and some androstane brassinolide analogs
    1987, Vol. 52, Issue 4, pp. 1026–1042 [Abstract]
  • Ladislav Kohout, Helena Velgová, Miroslav Strnad and Miroslav Kamínek
    Brassino steroids with androstane and pregnane skeleton
    1987, Vol. 52, Issue 2, pp. 476–486 [Abstract]
  • Václav Černý, Jaroslav Zajíček and Miroslav Strnad
    2α,3α-Dihydroxy-7-oxa-6-oxo-B-homo-5α-pregnan-21-oic acid and its derivatives as brassinolide analogues
    1987, Vol. 52, Issue 1, pp. 215–222 [Abstract]
  • Ladislav Kohout
    Solvolytic reactions of epimeric 3-methanesulfonyloxy-7-benzoyloxy-5α,6α-cyclopropanocholestanes
    1986, Vol. 51, Issue 10, pp. 2222–2231 [Abstract]
  • Václav Černý, Miroslav Strnad and Miroslav Kamínek
    Preparation of 2α,3α-dihydroxy-7-oxa-6-oxo-23,24-dinor-B-homo-5α-cholanic acid, its esters and amides as brassinolide analogues
    1986, Vol. 51, Issue 3, pp. 687–697 [Abstract]
  • Ladislav Kohout and Miroslav Strnad
    Brassinosteroids with a cholestane side chain
    1986, Vol. 51, Issue 2, pp. 447–458 [Abstract]
  • Ladislav Kohout, Vijay Kumar Sethi, Jaroslav Zajíček and Alexander Kasal
    Solvolytic reactions of empiric 3-methanesulfonyloxy-7-benzoyloxy-5β,6β-cyclopropanocholestanes
    1986, Vol. 51, Issue 2, pp. 436–446 [Abstract]
  • Ladislav Kohout
    The synthesis of 5,6-cyclopropanocholestanes with oxygen functions in positions 3 and 7
    1986, Vol. 51, Issue 2, pp. 429–435 [Abstract]
  • Alexander Kasal, Ladislav Kohout and Jiří Filip
    4,5-Secoandrostanes by Eschenmoser's reaction
    1985, Vol. 50, Issue 6, pp. 1402–1414 [Abstract]
  • Helena Velgová and Ladislav Kohout
    6,7-Secoandrostane derivatives
    1985, Vol. 50, Issue 4, pp. 962–972 [Abstract]
  • Ladislav Kohout and Jaroslav Zajíček
    Lead tetraacetate oxidation of 3β-acetoxy-B-homo-5α-cholestan-7aβ-ol
    1984, Vol. 49, Issue 1, pp. 301–305 [Abstract]
  • Ladislav Kohout and Alexander Kasal
    Electrophilic addition to the 5,6-double bond in A-nor-3,5-secosteroids
    1983, Vol. 48, Issue 7, pp. 2051–2063 [Abstract]
  • Alexander Kasal, Luboš Stárka, Richard Hampl and Ladislav Kohout
    Preparation and pharmacological properties of 4,5-secopregnane-3,20-dione and its derivatives
    1983, Vol. 48, Issue 7, pp. 2040–2050 [Abstract]
  • Ladislav Kohout, Alexander Kasal, Vlastimil Šanda and Helena Velgová
    Rearrangement of the 16,17-cyclopropano derivatives
    1983, Vol. 48, Issue 1, pp. 173–183 [Abstract]
  • Ladislav Kohout, Vlastimil Šanda and Jan Fajkoš
    Synthesis of two isomeric 16,17-cyclopropano derivatives of 5-pregnene
    1982, Vol. 47, Issue 5, pp. 1503–1513 [Abstract]
  • Alexander Kasal and Ladislav Kohout
    4,5-Secoanalogues of dihydrotestosterone with a cyclopropane ring in the position 5(6)
    1982, Vol. 47, Issue 1, pp. 130–143 [Abstract]
  • Ladislav Kohout
    Synthesis of 5,6-cyclopropanocholestane derivatives with an oxygen function in position 7
    1981, Vol. 46, Issue 8, pp. 1828–1838 [Abstract]
  • František Tureček and Ladislav Kohout
    The stereospecific loss of water from B-homocholestanols under electron impact
    1980, Vol. 45, Issue 9, pp. 2433–2442 [Abstract]
  • Ladislav Kohout and Jan Fajkoš
    Analogues of androgens with a cyclopropane ring in 6α,7α-position
    1980, Vol. 45, Issue 7, pp. 1974–1981 [Abstract]
  • Pavel Kočovský, Ladislav Kohout and Václav Černý
    Participation of 19-substituents in electrophilic additions to 6,7-unsaturated 5α-cholestane and B-homo 5α-cholestane derivatives; A case of competition between the participation of an ambident neighboring group and external nucleophile attack
    1980, Vol. 45, Issue 2, pp. 559–583 [Abstract]
  • Vlastimil Šanda, Ladislav Kohout and Jan Fajkoš
    5,7-Cyclo-B-homopregnane derivatives with the corticoid ketol side chain
    1980, Vol. 45, Issue 1, pp. 269–273 [Abstract]
  • Ladislav Kohout and Jan Fajkoš
    Acetolysis of 4β-methanesulphonyloxy-6β,7aβ-cyclo-B-homo-5α-cholestane
    1979, Vol. 44, Issue 11, pp. 3308–3320 [Abstract]
  • Bruno Schönecker, Dieter Tresselt, Gerd Schubert, Ladislav Kohout and Jan Fajkoš
    1H-NMR investigations. Application of trichloroacetyl isocyanate to structure determination of 3-, 6-, 7-, 7a- and 17-hydroxy steroids
    1978, Vol. 43, Issue 10, pp. 2609–2618 [Abstract]
  • Ladislav Kohout and Jan Fajkoš
    Methylenation of 4,6-cholestadien-3-one
    1978, Vol. 43, Issue 4, pp. 1134–1141 [Abstract]
  • Ladislav Kohout
    2,3-Disubstituted derivatives of the 6β,7aβ-cyclo-B-homo-5α-cholestane series
    1978, Vol. 43, Issue 3, pp. 889–899 [Abstract]
  • Ladislav Kohout and Jan Fajkoš
    Fission of the epimeric 2,3-epoxides in the 5,7β-cyclo-B-homo-5β-cholestane series
    1978, Vol. 43, Issue 2, pp. 638–646 [Abstract]