Collect. Czech. Chem. Commun. 2004, 69, 1805-1817
https://doi.org/10.1135/cccc20041805

Synthetic Approach to 5α-Pregnanolone 19-[O-(Carboxymethyl)oxime] Derivatives

Ivan Černýa, Helena Havlíkováb, Martin Hillb, Richard Hamplb and Vladimír Pouzara,*

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
b Institute of Endocrinology, Národní 8, 116 98 Prague 1, Czech Republic

Individual author index pages


Other CCCC articles of these authors

  • 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]
  • Miroslav Reschel, Miloš Buděšínský, Ivan Černý, Vladimír Pouzar and Pavel Drašar*
    Synthesis of Linear Steroid Oligoesters Based on Etienic Acid
    2002, Vol. 67, Issue 11, pp. 1709–1718 [Abstract]
  • Martin Hill*, Helena Havlíková, Jan Klak, Marie Bičíková, Vladimír Pouzar, Richard Hampl and Luboslav Stárka
    Rapid Immunoassay for Pregnenolone Sulfate and Its Applications in Endocrinology
    2002, Vol. 67, Issue 1, pp. 140–162 [Abstract]
  • Richard Hampl*, Martin Hill and Luboslav Stárka
    Detection and Quantification of 7-Hydroxydehydroepiandrosterone Epimers in Three Body Fluids
    2002, Vol. 67, Issue 1, pp. 10–18 [Abstract]
  • Ivan Černý*, Miloš Buděšínský, Vladimír Pouzar and Pavel Drašar
    Linear Chaining of Etienic Acid Derivatives with the Amide Bond. Synthesis of Oligomeric Steroids
    2001, Vol. 66, Issue 6, pp. 933–946 [Abstract]
  • Ivan Černý*, Vladimír Pouzar, Miloš Buděšínský and Pavel Drašar
    Synthesis of Symmetrical Bis-Steroid Pyrazines Connected via D-Rings
    2000, Vol. 65, Issue 10, pp. 1597–1608 [Abstract]
  • Vladimír Pouzar*, Ivan Černý and Pavel Drašar
    Coupling of Steroid O-(Carboxymethyl)oxime Derivatives with Single-Protected α,ω-Diaminoalkanes
    1999, Vol. 64, Issue 12, pp. 2035–2043 [Abstract]
  • Luboslav Stárka, Martin Hill, Richard Hampl, Marie-Irène Malewiak, Aïda Benalycherif, Robert Morfin, Jaroslav Kolena and Sona Scsuková
    Studies on the Mechanism of Antiglucocorticoid Action of 7α-Hydroxydehydroepiandrosterone
    1998, Vol. 63, Issue 10, pp. 1683–1698 [Abstract]
  • Vladimír Pouzar, Tereza Slavíková and Ivan Černý
    Lengthening of the Alkyl Chain in Steroid O-(ω-Carboxyalkyl)oximes by Wittig Reaction
    1998, Vol. 63, Issue 10, pp. 1623–1634 [Abstract]
  • Tereza Slavíková, Vladimír Pouzar and Ivan Černý
    Synthesis of Steroid O-(ω-Hydroxyalkyl)oximes by Reduction of Corresponding O-(ω-Carboxyalkyl)oxime Derivatives
    1998, Vol. 63, Issue 4, pp. 557–576 [Abstract]
  • Ivan Černý, Vladimír Pouzar, Oldřich Lapčík and Richard Hampl
    Addition of Azoimide to Unsaturated Ketones in the Steroid Series. Synthesis of N-(17β-Hydroxy-3-oxo-5α-androstan-15β-yl)succinamoic Acid and Its Evaluation as Hapten for Dihydrotestosterone Immunoanalysis
    1997, Vol. 62, Issue 12, pp. 1931–1939 [Abstract]
  • Ivan Černý, Tereza Slavíková and Vladimír Pouzar
    Synthesis of (15E)-17β-hydroxy-5α-androstane-3,15-dione 15-[O-(Carboxymethyl)]oxime, New Hapten for Dihydrotestosterone (17β-hydroxy-5α-androstan-3-one)
    1997, Vol. 62, Issue 10, pp. 1642–1649 [Abstract]
  • Tereza Slavíková, Vladimír Pouzar and Ivan Černý
    Syntheses of Steroid O-(3-Carboxypropyl)oximes
    1997, Vol. 62, Issue 3, pp. 457–470 [Abstract]
  • Vladimír Pouzar, Tereza Slavíková and Ivan Černý
    Synthesis of (19E)-3β,7β-Dihydroxy-17-oxoandrost-5-en-19-al 19-(O-Carboxymethyl)oxime, New Hapten for 7β-Hydroxydehydroepiandrosterone (3β,7β-Dihydroxyandrost-5-en-17-one)
    1997, Vol. 62, Issue 1, pp. 109–123 [Abstract]
  • Jan Fajkoš, Vladimír Pouzar and Ivan Černý
    Synthesis of (15E)-3β-Hydroxyandrost-5-ene-15,17-dione 15-(O-Carboxymethyl)oxime; The New Hapten for 3β-Hydroxyandrost-5-en-17-one (Dehydroepiandrosterone, DHEA)
    1996, Vol. 61, Issue 11, pp. 1647–1654 [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]
  • Vladimír Pouzar, Tereza Slavíková and Ivan Černý
    Preparation of 7-[O-(Carboxymethyl)oxime] Derivatives of Dehydroepiandrosterone and Pregnenolone
    1996, Vol. 61, Issue 3, pp. 404–412 [Abstract]
  • Vladimír Pouzar and Ivan Černý
    Coupling of Steroid O-(Carboxymethyl)oxime Derivatives with Amino Alcohols
    1996, Vol. 61, Issue 2, pp. 288–297 [Abstract]
  • Jasmina Novakovic, Eva Tvrzická, Václav Všetečka, Vladimír Pouzar and Ladislav Feltl
    Capillary Gas-Chromatographic Retention Behavior and Physico-Chemical Properties of Underivatized Equine Estrogens
    1995, Vol. 60, Issue 5, pp. 813–819 [Abstract]
  • Vladimír Pouzar and Ivan Černý
    Preparation of (20E)-21-Ethoxycarbonyl-14β,17α-pregna-5,20-dien-3β-yl Hydrogen Butanedioate
    1995, Vol. 60, Issue 4, pp. 715–718 [Abstract]
  • Miloš Buděšínský, Miloslav Černý, Ivan Černý, Stanislav Sámek and Tomáš Trnka
    Preparation of β-D-Glucopyranosyl Derivatives of 1,6:2,3- and 1,6:3,4-Dianhydro-β-D-hexopyranoses and Their 1H and 13C NMR Spectra
    1995, Vol. 60, Issue 2, pp. 311–323 [Abstract]
  • Vladimír Pouzar and Ivan Černý
    17-(O-(2-Carboxyethyl)oxime) Derivatives of Androstanes of 3-Hydroxy-5α-, -5β-, -5-ene and 3-Oxo-4-ene Series
    1995, Vol. 60, Issue 1, pp. 137–149 [Abstract]
  • Ivan Černý, Miloš Buděšínský, Pavel Drašar and Vladimír Pouzar
    Construction of the Side-Chain in 14β-Androst-5-ene Derivatives. Preparation of 14β-Pregnenolone
    1994, Vol. 59, Issue 12, pp. 2691–2704 [Abstract]
  • Vladimír Pouzar and Ivan Černý
    Preparation of (17E)-3β-Hydroxyandrost-5-en-17-one (O-Carboxymethyl)oxime Derivatives with Short Peptide Chain
    1994, Vol. 59, Issue 9, pp. 2042–2056 [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]
  • Vladimír Pouzar, Ivan Černý and Pavel Drašar
    Acrylate Side Chain Derivatives of 5β-Steroids
    1993, Vol. 58, Issue 12, pp. 2963–2976 [Abstract]
  • Libuše Arnoštová, Ivan Černý, Vladimír Pouzar and Pavel Drašar
    Synthesis of 5α-Cholestane Type Glycoside Sulfates
    1993, Vol. 58, Issue 5, pp. 1180–1190 [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]
  • Vladimír Pouzar, Ivan Černý and Pavel Drašar
    Z-Isomers of Steroid 17β-Side Chain Methyl Acrylates
    1992, Vol. 57, Issue 9, pp. 1928–1936 [Abstract]
  • Lenka Schneiderová, Oldřich Štrouf, Bohumír Grüner, Vladimír Pouzar, Pavel Drašar, Richard Hampl and Irena Kimlová
    Synthesis of o-Carboranylmethyl Ethers of Steroids as Potential Target Substrates for Boron Neutron Capture Therapy
    1992, Vol. 57, Issue 3, pp. 463–471 [Abstract]
  • Ivan Černý, Vladimír Pouzar, Pavel Drašar and Miroslav Havel
    Glucosylation of Some Steroidal 17-Hydroxy Derivatives
    1992, Vol. 57, Issue 2, pp. 362–374 [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]
  • Jan Fajkoš and Vladimír Pouzar
    Synthesis of (19E)-17β-hydroxy-3-oxo-5α-androstan-19-al 19-(O-carboxymethyl)oxime
    1991, Vol. 56, Issue 12, pp. 2884–2891 [Abstract]
  • Jan Fajkoš, Vladimír Pouzar and Karel Vereš
    Synthesis of (19E)-3,20-dioxopregn-4-en-19-al 19-(O-carboxymethyl)oxime
    1991, Vol. 56, Issue 5, pp. 1087–1092 [Abstract]
  • Ivan Černý, Vladimír Pouzar, Miloš Buděšínský, Pavel Drašar and Miroslav Havel
    Epimeric 17-hydroxy derivatives of 14β-androst-5-en-3β-yl acetate
    1990, Vol. 55, Issue 10, pp. 2510–2520 [Abstract]
  • Jan Fajkoš, Vladimír Pouzar and Karel Vereš
    Synthesis of (19E)-17β-hydroxy-3-oxoandrost-4-en-19-al 19-(O-carboxymethyl)oxime
    1990, Vol. 55, Issue 8, pp. 2086–2094 [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, Ivan Černý, Pavel Drašar and Miroslav Havel
    Preparation of (20E)-21-ethoxycarbonyl-5β-pregn-20-en-3β-yl hydrogen butanedioate
    1990, Vol. 55, Issue 6, pp. 1635–1638 [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]
  • Vladimír Pouzar, Dalibor Sameš and Miroslav Havel
    Preparation of selectively protected derivatives of 21-nor-5-pregnene-3β,20-diol
    1990, Vol. 55, Issue 2, pp. 499–511 [Abstract]
  • Pavel Drašar, Vladimír Pouzar, Ivan Černý, George R. Pettit and Miroslav Havel
    Synthesis and in vitro antimetabolic evaluation of some steroidal thiazoles
    1989, Vol. 54, Issue 12, pp. 3339–3347 [Abstract]
  • Ivan Černý, Petr Novotný, Pavel Drašar, Miroslav Havel and Josef Pacák
    Glycosylation of steroids with silver silicate and 2-deoxy-2-fluoro-α-D-glucopyranosyl bromide triacetate
    1989, Vol. 54, Issue 10, pp. 2775–2783 [Abstract]
  • Vladimír Pouzar, Lenka Schneiderová, Pavel Drašar, Oldřich Štrouf and Miroslav Havel
    Synthesis of 2-propynyl ethers of steroid alcohols
    1989, Vol. 54, Issue 7, pp. 1888–1902 [Abstract]
  • Vladimír Pouzar, Lenka Kárászová and Miroslav Havel
    Preparation of 21-methoxycarbonyl-21-methylene-5-pregnen-3β-ol derivatives
    1987, Vol. 52, Issue 11, pp. 2735–2743 [Abstract]
  • Ivan Černý, Vladimír Pouzar, Pavel Drašar and Miroslav Havel
    β-Glucosides of steroidal unsaturated nitriles
    1987, Vol. 52, Issue 10, pp. 2521–2533 [Abstract]
  • Vladimír Pouzar, Ivan Černý, Pavel Drašar and Miroslav Havel
    Preparation of (20E)-21-methoxycarbonyl-5,14,20-pregnatrien-3β-ol derivatives
    1987, Vol. 52, Issue 7, pp. 1803–1810 [Abstract]
  • Vladimír Pouzar, Ivan Černý, Pavel Drašar, Soňa Vašíčková and Miroslav Havel
    Preparation of 3β-hydroxy-21,26,27-trinorcholesta-5,23-dien-25→22-olide and 3β-hydroxy-20-(2-furyl)-21-nor-5-pregnene derivatives
    1987, Vol. 52, Issue 4, pp. 1043–1051 [Abstract]
  • Vladimír Pouzar, Ivan Černý, Pavel Drašar and Miroslav Havel
    New approach to steroidal hemisuccinates and glycosides
    1987, Vol. 52, Issue 3, pp. 775–787 [Abstract]
  • Vladimír Pouzar, Ivan Černý, Pavel Drašar and Miroslav Havel
    New method of preparation of cardioglycoside hemisuccinates
    1986, Vol. 51, Issue 9, pp. 2019–2028 [Abstract]
  • Ivan Černý, Vladimír Pouzar, Pavel Drašar, František Tureček and Miroslav Havel
    Steroids with the β-crotonate (2-butenoate) side chain
    1986, Vol. 51, Issue 1, pp. 128–140 [Abstract]
  • Soňa Vašíčková, Vladimír Pouzar, Ivan Černý, Pavel Drašar and Miroslav Havel
    Infrared spectra of compounds with the methoxymethyl protecting group
    1986, Vol. 51, Issue 1, pp. 90–100 [Abstract]
  • Pavel Drašar, Vladimír Pouzar, Ivan Černý, Miroslav Havel, František Tureček, Daniela Schmiedová and Karel Vereš
    Preparation of 3-carboxypropanoates of digitoxin and digoxin and their conjugates with L-tyrosine
    1985, Vol. 50, Issue 12, pp. 2760–2774 [Abstract]
  • Vladimír Pouzar, Pavel Drašar, Ivan Černý and Miroslav Havel
    Preparation and absolute configuration at C(22) of 21,26,27-trinor-5α-cholestan-25→22-olide derivatives
    1985, Vol. 50, Issue 4, pp. 869–877 [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]
  • Pavel Drašar, Vladimír Pouzar, Ivan Černý and Miroslav Havel
    Synthesis of 4-(21-nor-5-pregnen-20-yl)-1,3-thiazole derivatives
    1984, Vol. 49, Issue 4, pp. 1051–1059 [Abstract]
  • Pavel Drašar, Vladimír Pouzar, Ivan Černý, Jorga Smolíková and Miroslav Havel
    Synthesis of 17β-[4-(1,3-thiazolyl)]androstane 3β-hemisuccinate and glycoside
    1984, Vol. 49, Issue 4, pp. 1039–1050 [Abstract]
  • Ivan Černý, Vladimír Pouzar, Pavel Drašar, Miloš Buděšínský and Miroslav Havel
    Glucosylation of 5-androsten-3β-ol derivatives containing butenolide, furan or unsaturated ester moieties in the side chain
    1984, Vol. 49, Issue 4, pp. 881–891 [Abstract]
  • Vladimír Pouzar, Pavel Drašar, Ivan Černý and Miroslav Havel
    Preparation of 21,26,27-trinor-5α-cholest-23-en-25→20-olide from a propargyl synthone
    1984, Vol. 49, Issue 4, pp. 871–880 [Abstract]
  • Ivan Černý, Tomáš Trnka and Miloslav Černý
    Azido derivatives of 1,6-anhydro-β-D-hexopyranoses corresponding to 3-deoxy- and 4-deoxy-D-glucosamine
    1984, Vol. 49, Issue 2, pp. 433–443 [Abstract]
  • Pavel Drašar, Ivan Černý, Vladimír Pouzar and Miroslav Havel
    New preparation of steroidal 3-hemisuccinates
    1984, Vol. 49, Issue 1, pp. 306–312 [Abstract]
  • Vladimír Pouzar, Soňa Vašíčková, Pavel Drašar, Ivan Černý and Miroslav Havel
    Preparation and absolute configuration at C(22) of 21,26,27-trinor-5α-cholestane-22,25-diol derivatives
    1983, Vol. 48, Issue 8, pp. 2423–2435 [Abstract]
  • Ivan Černý, Tomáš Trnka and Miloslav Černý
    Preparation of 2-amino-2,4-dideoxy-D-lyxo-hexopyranose (4-deoxy-D-mannosamine) from 1,6-anhydro-β-D-glucopyranose
    1983, Vol. 48, Issue 8, pp. 2386–2394 [Abstract]
  • Ivan Černý, Vladimír Pouzar, Pavel Drašar and Miroslav Havel
    Synthesis of 17β-steroidal 4-(2-butenolides)
    1983, Vol. 48, Issue 7, pp. 2064–2071 [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]
  • Pavel Drašar, Vladimír Pouzar, Ivan Černý and Miroslav Havel
    Alternative syntheses of steroidal maleimides
    1983, Vol. 48, Issue 4, pp. 1224–1232 [Abstract]
  • Jiří Křepelka, Vladimír Pouzar, Jiří Schlanger, Jiří Holubek, Jiří Körbl, Fedir Jančik and Rudolf Kotva
    Oxidative transformations of some pyrimidine derivatives into oxazolidine derivatives
    1983, Vol. 48, Issue 4, pp. 1212–1223 [Abstract]
  • Jiří Křepelka, Jan Beneš, Vladimír Pouzar, Jaroslav Vachek and Jiří Holubek
    Some 2-substitution derivatives of 5-(4-oxo-6-hydroxy-3,4-dihydro-5-pyrimidinyl)pentanoic acid
    1983, Vol. 48, Issue 1, pp. 304–311 [Abstract]
  • Pavel Drašar, Vladimír Pouzar, Ivan Černý, Miroslav Havel, Sofia N. Ananchenko and Igor V. Torgov
    Use of malonic acid derivatives for the construction of substituted side chains in the position 17β of steroids
    1982, Vol. 47, Issue 4, pp. 1240–1251 [Abstract]
  • Pavel Kočovský, Pavel Drašar, Vladimír Pouzar and Miroslav Havel
    Synthesis of some westphalen-type cardenolide analogs
    1982, Vol. 47, Issue 1, pp. 108–116 [Abstract]
  • Vladimír Pouzar, Pavel Drašar, Pavel Kočovský and Miroslav Havel
    Synthesis of some isocardenolide analogs and 17β-maleimidoandrostane of westphalen structural type
    1982, Vol. 47, Issue 1, pp. 96–107 [Abstract]
  • Vladimír Pouzar and Miroslav Havel
    Synthesis and absolute configuration at C(20) of 21,26,27-trinor-5α-cholestan-25→20-olide derivatives
    1981, Vol. 46, Issue 11, pp. 2758–2765 [Abstract]
  • Vladimír Pouzar and Miroslav Havel
    Preparation and absolute configuration at C(20) of 21-nor-5α-chol-22-en-24→20-olide derivatives
    1981, Vol. 46, Issue 4, pp. 917–925 [Abstract]
  • Vladimír Pouzar and Miroslav Havel
    Preparation and absolute configuration at C(20) of 21-nor-5α-cholan-24→20-olide derivatives
    1981, Vol. 46, Issue 1, pp. 107–117 [Abstract]
  • Vladimír Pouzar and Miroslav Havel
    Absolute configuration at C(20) of the derivatives of 21-nor-5α-cholane-20,24-diol
    1980, Vol. 45, Issue 9, pp. 2443–2451 [Abstract]
  • Miloslav Černý, Hana Večerková, Ivan Černý and Josef Pacák
    Preparation of 2-amino-1,6-anhydro-2-deoxy-β-D-mannopyranose by intramolecular substitution of the tosyloxy group in sterically hindered position of 1,6-anhydro-2-O-p-tolylsulfonyl-β-D-glucopyranose
    1980, Vol. 45, Issue 6, pp. 1837–1844 [Abstract]
  • Vladimír Pouzar and Alois Vystrčil
    Preparation of 12,20-disubstituted lupane derivatives
    1979, Vol. 44, Issue 1, pp. 194–210 [Abstract]
  • Vladimír Pouzar and Alois Vystrčil
    Preparation of 29-acetoxy-30-norlupan-20-one derivatives with the substituted ring C
    1978, Vol. 43, Issue 8, pp. 2190–2203 [Abstract]