Collect. Czech. Chem. Commun. 1998, 63, 1528-1542
https://doi.org/10.1135/cccc19981528

Long-Range Effect of 17-Substituents in 3-Oxo Steroids on 4,5-Double Bond Hydrogenation

Romana Šídová, Karel Stránský, Alexander Kasal, Barbora Slavíková and Ladislav Kohout

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

Individual author index pages


Other CCCC articles of these authors

  • Miloš Buděšínský, Jan Fajkoš, Jaroslav Günter and Alexander Kasal*
    Synthesis, Reactions, Conformation Analysis, and NMR Spectra of 5,10-Epoxy-5ξ,10ξ-estrane-3,17-diones
    2005, Vol. 70, Issue 4, pp. 507–518 [Abstract]
  • Libor Matyáš, Alexander Kasal*, Zoila Babot Riera and Cristina E. Sunol
    Effects of 3α-Amino-5α-pregnan-20-one on GABAA Receptor: Synthesis, Activity and Cytotoxicity
    2004, Vol. 69, Issue 7, pp. 1506–1516 [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]
  • 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]
  • Ladislav Kohout*, Hana Chodounská, Tomáš Macek and Miroslav Strnad
    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
    2000, Vol. 65, Issue 11, pp. 1754–1761 [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]
  • Alexander Kasal*, Miloš Buděšínský, Jan Pelnař, Michael A. Bruck* and Michael F. Brown
    Structures and Synthesis of 4a-Homo-7,19-dinorsteroids, X-Ray Crystallography and NMR Spectroscopy
    1999, Vol. 64, Issue 12, pp. 2019–2034 [Abstract]
  • Barbora Slavíková* and Alexander Kasal
    Epalons: Synthesis of New 16α-Carboxymethyl Derivatives
    1999, Vol. 64, Issue 9, pp. 1479–1484 [Abstract]
  • Alexander Kasal
    Epalons: Synthesis of 7-Norallopregnanolone
    1999, Vol. 64, Issue 9, pp. 1471–1478 [Abstract]
  • Barbora Slavíková, Alexander Kasal* and Miloš Buděšínský
    Autoxidation vs Hydrolysis in 16α-Acyloxy Steroids
    1999, Vol. 64, Issue 7, pp. 1125–1134 [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]
  • Alexander Kasal, Jiří Polman and Miloš Buděšínský
    Hydrogenation of a Tetrasubstituted Double Bond: Synthesis of 5-Methyl-19-nor-5β-pregnanes
    1998, Vol. 63, Issue 10, pp. 1549–1563 [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]
  • Karel Stránský and Irena Valterová
    Gas Chromatography and Mass Spectrometry of Isomeric Cyclohexylnonadecanes and 1-Cyclopentylicosane
    1998, Vol. 63, Issue 10, pp. 1513–1521 [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]
  • Barbora Slavíková, Alexander Kasal and Miloš Buděšínský
    Dihydrotestosterone with an Ammonium Centre in the Position 16β
    1997, Vol. 62, Issue 4, pp. 656–664 [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]
  • Oldřich Lapčík, Richard Hampl, Martin Hill, Luboslav Stárka, Alexander Kasal, Vladimír Pouzar and Zdeněk Putz
    Radioimmunological and Chromatographic Properties of Tyrosine Methyl Ester Conjugates with Stereoisomeric Steroid Carboxy Derivatives
    1996, Vol. 61, Issue 5, pp. 799–807 [Abstract]
  • Alexander Kasal and Miloš Buděšínský
    Partial Modifications of Hydroxy Groups in 5-Methyl-5β-estr-9-ene Derivatives
    1996, Vol. 61, Issue 2, pp. 276–287 [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]
  • Alexander Kasal
    Synthesis of 17α-Hydroxy Steroids: B-Norepitestosterone
    1993, Vol. 58, Issue 9, pp. 2202–2210 [Abstract]
  • Alexander Kasal and Světlana Pásztorová
    Synthesis of RIA Haptens: 3α,11α-Dihydroxy-5α-pregnan-20-one 11-Hemisuccinate
    1993, Vol. 58, Issue 3, pp. 619–628 [Abstract]
  • Alexander Kasal, Květa Fuksová and Vladimír Pouzar
    Preparation of Unlabelled and [3H]-Labelled Epitestosterone and Its Metabolites
    1993, Vol. 58, Issue 3, pp. 600–611 [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]
  • Karel Stránský, Marta Semerdžieva, Miroslav Otmar, Želimír Procházka, Miloš Buděšínský, Karel Ubik, Jitka Kohoutová and Ludvík Streinz
    Antifungal Antibiotic from the Mushroom Agrocybe aegerita (BRIG.) SING.
    1992, Vol. 57, Issue 3, pp. 590–603 [Abstract]
  • Jiří Polman and Alexander Kasal
    The synthesis of 5-methyl-19-nor-5β-pregna-9,16-diene-3,20-dione, 5-methyl-19-nor-5β-pregna-9,10-diene-3,6,20-trione and their analogues with annellated E ring
    1991, Vol. 56, Issue 12, pp. 2892–2905 [Abstract]
  • Miloš Buděšínský, Alexander Kasal, Želimír Procházka, Huynh Kim Thoa, Soňa Vašíčková and Pavel Kočovský
    Revision of the structure of 3-methoxy-14α-hydroxy-D-homo-1,3,5-(10)-estratrien-17a-one. A simple 1H NMR method for the determination of configuration of hydroxy group in position 5 and/or 14 of the D-homo-steroid skeleton
    1991, Vol. 56, Issue 7, pp. 1512–1524 [Abstract]
  • Alexander Kasal, Jenny Pokorná and Jaroslav Zajíček
    3β,11α,17-Trihydroxy-5-pregnen-20-one 11-hemisuccinate as a haptene for RIA of "17α-hydroxypregnenolone"
    1991, Vol. 56, Issue 6, pp. 1340–1347 [Abstract]
  • Karel Stránský, Milan Streibl and Karel Ubik
    Unusual alkanes pattern of some plant cuticular waxes
    1991, Vol. 56, Issue 5, pp. 1123–1129 [Abstract]
  • Alexander Kasal, Jaroslav Podlaha and Jaroslav Zajíček
    A-homo-B,19-dinorandrostanes from 6β-methanesulfonyloxy-5-methyl-19-nor-5β-androst-9-ene derivatives
    1991, Vol. 56, Issue 5, pp. 1070–1086 [Abstract]
  • Jiří Polman and Alexander Kasal
    Synthesis of 5-methyl-19-nor-5β-pregn-9-ene derivatives
    1990, Vol. 55, Issue 7, pp. 1783–1791 [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]
  • Alexander Kasal
    Antiandrogenic A-homo-B,19-dinorandrostanes from 5β-methyl-19-norandrost-9-enes with different substituents in positions 3 and 17
    1989, Vol. 54, Issue 8, pp. 2218–2228 [Abstract]
  • Alexander Kasal and Jaroslav Zajíček
    Spontaneous transannular reaction in Δ9-unsaturated A-homo-B,19-dinorsteroids
    1989, Vol. 54, Issue 5, pp. 1327–1335 [Abstract]
  • Alexander Kasal
    Antiandrogenic A-homo-B,19-dinor-analogues of androgens from 6β-chloro-5-methyl-19-nor-5β-androst-9-enes
    1989, Vol. 54, Issue 5, pp. 1318–1326 [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]
  • 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]
  • Ladislav Kohout
    Solvolytic reactions of epimeric 3-methanesulfonyloxy-7-benzoyloxy-5α,6α-cyclopropanocholestanes
    1986, Vol. 51, Issue 10, pp. 2222–2231 [Abstract]
  • Alexander Kasal and Jaroslav Zajíček
    Solvolysis of Westphalen-type compounds
    1986, Vol. 51, Issue 7, pp. 1462–1475 [Abstract]
  • Miloš Buděšínský, Antonín Trka, Karel Stránský and Milan Streibl
    Heterocyclic nitrogen-containing compounds from the extract of the springtail Tetrodontophora bielanensis (WAGA)
    1986, Vol. 51, Issue 4, pp. 956–963 [Abstract]
  • Karel Stránský, Antonín Trka, Miloš Buděšínský and Milan Streibl
    Lipidic compounds from the extract of the springtail Tetrodontophora bielanensis (WAGA)
    1986, Vol. 51, Issue 4, pp. 948–955 [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]
  • Luboslav Stárka, Alexander Kasal, Marie Bičíková and Richard Hampl
    Preparation and synandrogenic activity of 17β-hydroxy-4,5-seco-5-androsten-3-one
    1984, Vol. 49, Issue 12, pp. 2942–2947 [Abstract]
  • Alexander Kasal and Jorga Smolíková
    Photochemical 6β-hydroxylation of 11β-hydroxy-4-androstene-3,17-dione
    1984, Vol. 49, Issue 12, pp. 2932–2941 [Abstract]
  • Alexander Kasal
    A new type of A-homo-B-norcholestane derivatives
    1984, Vol. 49, Issue 4, pp. 892–902 [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]
  • Alexander Kasal
    4-Thia-5-cholesten-3-one and some further steroidal δ-thioenol lactones
    1983, Vol. 48, Issue 5, pp. 1489–1498 [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]
  • Alexander Kasal
    Desulfuration of steroidal thians
    1982, Vol. 47, Issue 11, pp. 3148–3159 [Abstract]
  • Antonín Trka and Alexander Kasal
    Inductive effect in EI-mass spectra of some 5,6-dihalogenides and 5,6-halohydrins of 5α-cholestan-3β-ol and 3β-acetoxy-5α-cholestane
    1982, Vol. 47, Issue 11, pp. 2946–2960 [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]
  • Oldřich Kocián, Karel Stránský and Jiří Závada
    Heteroanalogues of 1-triacontanol
    1982, Vol. 47, Issue 5, pp. 1356–1366 [Abstract]
  • Oldřich Kocián, Karel Stránský and Jiří Závada
    Unsaturated analogues of 1-triacontanol
    1982, Vol. 47, Issue 5, pp. 1346–1355 [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]
  • Alexander Kasal
    Hydrogenation of 12-oxo-5β-chol-9(11)-enates on platinum
    1981, Vol. 46, Issue 8, pp. 1839–1849 [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]
  • Alexander Kasal and Antonín Trka
    Splitting off of water from the molecular ions of steroidal cyclopropyl ketones
    1980, Vol. 45, Issue 11, pp. 2985–2997 [Abstract]
  • Alexander Kasal
    Analogues of androgens with the open ring A
    1980, Vol. 45, Issue 9, pp. 2541–2549 [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]
  • Antonín Trka and Alexander Kasal
    Electron impact mass spectra of some vicinal trans-dihalo- and trans-hydroxyhalocholestanes
    1980, Vol. 45, Issue 6, pp. 1720–1733 [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]
  • Alexander Kasal
    Deoxygenation at the carbon C(5) of 3,6-cyclo-A-nor-3,5-secoandrostanes
    1979, Vol. 44, Issue 5, pp. 1619–1629 [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]
  • Alexander Kasal
    Synthesis of 3,6-cyclo-A-nor-3,5-secoandrostanes
    1978, Vol. 43, Issue 7, pp. 1778–1792 [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]
  • Alexander Kasal
    Reduction of some 3,6-cyclo-A-nor-3,5-seco-6β-cholestanes
    1978, Vol. 43, Issue 2, pp. 498–510 [Abstract]
  • Milan Streibl, Karel Stránský and Vlastimil Herout
    n-Alkanes of some tree barks
    1978, Vol. 43, Issue 1, pp. 320–326 [Abstract]