Collect. Czech. Chem. Commun. 1986, 51, 1532-1541
https://doi.org/10.1135/cccc19861532

4-Phenylalanine analogues of vasopressin: Synthesis, pharmacological and chiroptical properties

František Brtníka, Tomislav Bartha, Petr Maloňa, Ivo Friča, Vija E. Klušab and Karel Jošta

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague, Czechoslovakia
b Institute of Organic Synthesis, Academy of Sciences of the Latvian S.S.R., Riga, U.S.S.R.

Individual author index pages


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    1985, Vol. 50, Issue 6, pp. 1329–1334 [Abstract]
  • Jiří Farkaš and Ivo Frič
    Synthesis of 2,3,5-tri-O-benzoyl-D-pentofuranosyl cyanides and their CD spectra
    1985, Vol. 50, Issue 6, pp. 1291–1299 [Abstract]
  • Václav Čeřovský and Karel Jošt
    Enzymatically catalyzed synthesis of dipeptides of γ-carboxy-L-glutamic acid from benzyloxycarbonyl-γ-carboxy-DL-glutamic acid
    1985, Vol. 50, Issue 4, pp. 878–884 [Abstract]
  • Michal Lebl, Victor J. Hruby, Jiřina Slaninová and Tomislav Barth
    Solid phase synthesis and biological activities of oxytocin carba analogues containing threonine in position 4
    1985, Vol. 50, Issue 2, pp. 418–427 [Abstract]
  • Michal Lebl, Tomislav Barth, Linda Servítová, Jiřina Slaninová and Karel Jošt
    Oxytocin analogues with inhibitory properties, containing in position 2 a hydrophobic amino acid of D-configuration
    1985, Vol. 50, Issue 1, pp. 132–145 [Abstract]
  • Václav Čeřovský and Karel Jošt
    Enzymatic resolution of γ-carboxy-DL-glutamic acid
    1984, Vol. 49, Issue 11, pp. 2562–2565 [Abstract]
  • Václav Čeřovský and Karel Jošt
    Papain-catalyzed synthesis of phenylhydrazides of N-acylamino acids
    1984, Vol. 49, Issue 11, pp. 2557–2561 [Abstract]
  • Michal Lebl, Tomislav Barth, Linda Servítová, Jiřina Slaninová and Pavel Hrbas
    Synthesis and properties of carba-6-analogues of oxytocin containing a deaminopenicillamine residue in position 1
    1984, Vol. 49, Issue 9, pp. 2012–2023 [Abstract]
  • Michal Lebl, Tomislav Barth, Denis J. Crankshaw, Bohuslav Černý, Edwin E. Daniel, A. K. Grover and Karel Jošt
    Synthesis and properties of [2-[3,5-3H2]-tyrosine,4-glutamic acid]deamino-1-carba-oxytocin
    1984, Vol. 49, Issue 8, pp. 1921–1926 [Abstract]
  • Karel Hauzer, Tomislav Barth, Linda Servítová and Karel Jošt
    Post-proline endopeptidase, further characterization of the enzyme from pig kidneys
    1984, Vol. 49, Issue 8, pp. 1846–1853 [Abstract]
  • Miloš Tichý, Ahmed M. Farag, Petr Maloň, Petr Kálal and Karel Bláha
    (3R)-5-Azatricyclo[4.3.1.03,8]decan-4-one, a lactam with a non-planar cis-amide group: Synthesis, geometry and chiroptical properties
    1984, Vol. 49, Issue 4, pp. 834–839 [Abstract]
  • Karel Bláha, Ahmed M. Farag, Dick VAN DER Helm, M. Bilayet Hossain, Miloš Buděšínský, Petr Maloň, Jorga Smolíková and Miloš Tichý
    Stereoisomeric chiral 2,9-diazabicyclo[4.4.0.]decane-3,10-diones as models of dipeptide grouping: Synthesis, X-ray, IR, NMR and cd studies
    1984, Vol. 49, Issue 3, pp. 712–742 [Abstract]
  • Zdenko Procházka, Michal Lebl, Tomislav Barth, Jan Hlaváček, Antonín Trka, Miloš Buděšínský and Karel Jošt
    Synthesis and properties of oxytocin analogues modified in the tripeptide side chain
    1984, Vol. 49, Issue 3, pp. 642–652 [Abstract]
  • Tomislav Barth, Pavel Hrbas, Jana Škopková, Hans Vilhardt, Martin Flegel and Karel Jošt
    The effect of some structural changes in the molecule of vasopressin on the duration of antidiuretic action
    1984, Vol. 49, Issue 1, pp. 137–140 [Abstract]
  • Daniel Butlen, Tomislav Barth, Bernard Cantau, Gilles Guillon, Serge Jard, Michal Lebl, František Brtník and Karel Jošt
    The structural requirements of oxytocin and vassopressin analogues for the activation of adenylate cyclase in the rat kidney medullary membrane system
    1983, Vol. 48, Issue 11, pp. 3166–3176 [Abstract]
  • František Brtník, Ivan Krejčí, Běla Kupková, Pavel Hrbas, Jana Škopková, Tomislav Barth and Karel Jošt
    Vasopressin analogues with effect on central nervous system: Synthesis and biological properties
    1983, Vol. 48, Issue 10, pp. 2862–2873 [Abstract]
  • Petr Maloň, Petr Pančoška, Miloš Buděšínský, Jan Hlaváček, Jan Pospíšek and Karel Bláha
    Chiroptical properties and conformation of N-acetyl-L-amino acids N'-methylamides with aliphatic side chains
    1983, Vol. 48, Issue 10, pp. 2844–2861 [Abstract]
  • Tomislav Barth, Bernard Cantau, Daniel Butlen, Gilles Guillon, Serge Jard, Michal Lebl and Karel Jošt
    Oxytocin and vasopressin analogues capable of competition with vasopressin binding to rat liver membranes
    1983, Vol. 48, Issue 6, pp. 1788–1795 [Abstract]
  • Michal Lebl, Pavel Hrbas, Jana Škopková, Jiřina Slaninová, Alena Machová, Tomislav Barth and Karel Jošt
    Synthesis and properties of oxytocin analogues with high and selective natriuretic activity
    1982, Vol. 47, Issue 9, pp. 2540–2560 [Abstract]
  • Zdenko Procházka, Miloš Buděšínský, Jorga Smolíková, Petr Trška and Karel Jošt
    1-Aminocyclopropanecarboxylic acid and its derivatives
    1982, Vol. 47, Issue 8, pp. 2291–2305 [Abstract]
  • Jiřina Slaninová, Iain C. A. F. Robinson, Pavel Hrbas and Tomislav Barth
    Cross-reactivity of anti-oxytocin sera
    1982, Vol. 47, Issue 6, pp. 1654–1658 [Abstract]
  • Karel Hauzer, Linda Servítová, Tomislav Barth and Karel Jošt
    Post-proline endopeptidase. Partial purification and characterization of the enzyme from pig kidneys
    1982, Vol. 47, Issue 4, pp. 1139–1148 [Abstract]
  • Karel Bláha, Miloš Buděšínský, Zdena Koblicová, Petr Maloň, Miloš Tichý, J. R. Baker, M. B. Hossain and Dick Van der Helm
    Optically active tricyclic dilactams with non-planar cis-amide groups: Synthesis, X-ray, NMR and CD studies
    1982, Vol. 47, Issue 3, pp. 1000–1019 [Abstract]
  • Michal Lebl, Jan Pospíšek, Jan Hlaváček, Tomislav Barth, Petr Maloň, Linda Servítová, Karel Hauzer and Karel Jošt
    Analogues of neurohypophysial hormones, containing tert-leucine: Synthesis and properties
    1982, Vol. 47, Issue 2, pp. 689–701 [Abstract]
  • Jan Hlaváček, Ivo Frič, Tomislav Barth and Karel Jošt
    [9-Aminoacetone]oxytocin and [8-p-aminobenzamide, 9-des-glycinamide]oxytocin: Chemical synthesis and properties
    1982, Vol. 47, Issue 1, pp. 338–348 [Abstract]
  • Igor Tvaroška, Slavomír Bystrický, Petr Maloň and Karel Bláha
    Non-planar conformations of methylacetamide: Solvent effect and chiroptical properties
    1982, Vol. 47, Issue 1, pp. 17–28 [Abstract]
  • Zdenko Procházka, Jorga Smolíková, Petr Maloň and Karel Jošt
    Synthetic utilization of α-amino-γ-bromobutyric acid in the preparation of non-coded amino acids; IR study of homoserine
    1981, Vol. 46, Issue 11, pp. 2935–2946 [Abstract]
  • Tomislav Barth, Jiřina Slaninová, Linda Servítová, Michal Lebl, Christine Kotsira-Engonopoulos, Chrysa Tzougraki, Iphigenia Photaki, Milan Krojidlo and Karel Jošt
    The effect of some structural modifications of the oxytocin molecule on the duration of the galactogogic response
    1981, Vol. 46, Issue 10, pp. 2441–2445 [Abstract]
  • Petr Šimek, Tomislav Barth, Miroslav Bárta, Vladimír Vojtíšek and Karel Jošt
    Resolution of S-benzyl-DL-penicillamine with penicillin amidohydrolase
    1981, Vol. 46, Issue 9, pp. 2263–2267 [Abstract]
  • František Brtník, Tomislav Barth and Karel Jošt
    Use of phenylacetyl group for protection of the lysine Nε-amino group in synthesis of peptides
    1981, Vol. 46, Issue 8, pp. 1983–1989 [Abstract]
  • Jana Škopková, Pavel Hrbas, Jiřina Slaninová and Tomislav Barth
    Prolonged antidiuretic action of vasopressin analogues in relation to their primary structure
    1981, Vol. 46, Issue 8, pp. 1850–1855 [Abstract]
  • Jiřina Slaninová, Michal Lebl, Tomislav Barth and Karel Jošt
    The effect of magnesium ions on the uterotonic activity of carba analogues of oxytocin modified in position 4
    1981, Vol. 46, Issue 7, pp. 1689–1692 [Abstract]
  • Zdenko Procházka, Michal Lebl, Linda Servítová, Tomislav Barth and Karel Jošt
    Synthesis and pharmacological properties of [2-p-fluorophenylalanine]deamino-1-carba-oxytocin and its diastereoisomeric sulfoxides
    1981, Vol. 46, Issue 4, pp. 947–956 [Abstract]
  • Asja Šiševa, Ljuben M. Sirakov, Jiřina Slaninová and Tomislav Barth
    Biological activity of some insulin derivatives
    1981, Vol. 46, Issue 1, pp. 300–302 [Abstract]
  • František Brtník, Milan Krojidlo, Tomislav Barth and Karel Jošt
    Synthesis of oxytocin, arginine-vasopressin and its deamino-analogue using 2,4,6-trimethylbenzyl group for protection of the cysteine sulfur
    1981, Vol. 46, Issue 1, pp. 286–299 [Abstract]
  • František Brtník, Tomislav Barth and Karel Jošt
    [7-Glycine]deamino-1-carba-vasopressin: Synthesis and pharmacological properties
    1981, Vol. 46, Issue 1, pp. 278–285 [Abstract]
  • Pavel Hrbas, Jiřina Slaninová, Tomislav Barth and František Franěk
    Cross-reactivity study of oxytocin antibodies with oxytocin and its analogues modified in the cyclic part of the molecule
    1981, Vol. 46, Issue 1, pp. 270–277 [Abstract]
  • Tomislav Barth, Jiřina Slaninová, Michal Lebl and Karel Jošt
    Biological activities and protracted action of carba-analogues of deamino-oxytocin with O-methyltyrosine in position 2
    1980, Vol. 45, Issue 11, pp. 3045–3050 [Abstract]
  • Michal Lebl, Tomislav Barth, Jana Škopková and Karel Jošt
    Synthesis and some pharmacological properties of [7-glycine, 8-ornithine]vasopressin and two of its analogues
    1980, Vol. 45, Issue 10, pp. 2865–2871 [Abstract]
  • Michal Lebl, Tomislav Barth and Karel Jošt
    Synthesis and pharmacological properties of oxytocin analogues modified simultaneously in position 2 and in the disulfide bridge
    1980, Vol. 45, Issue 10, pp. 2855–2864 [Abstract]
  • Michal Lebl, Alena Machová, Pavel Hrbas, Tomislav Barth and Karel Jošt
    Analogues of deamino-1-carba-oxytocin with an aliphatic amino acid in position 4: chemical synthesis and biological activities
    1980, Vol. 45, Issue 10, pp. 2714–2723 [Abstract]
  • Zdenko Procházka and Karel Jošt
    L-Cystathionine derivatives for the synthesis of peptides
    1980, Vol. 45, Issue 7, pp. 1982–1990 [Abstract]
  • Karel Hauzer, Siegfried Katzwinkel, Karel Jošt and Tomislav Barth
    The splitting of substance P by the post-proline cleaving enzyme from lamb kidneys
    1980, Vol. 45, Issue 6, pp. 1744–1747 [Abstract]
  • Zdenko Procházka and Karel Jošt
    Synthesis of the amino-terminal decapeptide of human calcitonin, in which the disulfide bond is replaced by a thioether group
    1980, Vol. 45, Issue 4, pp. 1305–1314 [Abstract]
  • Věra Klenerová, Miroslav Munclinger, Sixtus Hynie, Tomislav Barth and Karel Jošt
    Activation of adenylate cyclase from rat renal medulla by some oxytocin analogs
    1980, Vol. 45, Issue 4, pp. 1132–1136 [Abstract]
  • Ivo Frič, Lyudmila I. Leonteva, Petr Maloň, Karel Jošt and Karel Bláha
    Synthesis and chiroptical properties of heterodetic cyclic hexapeptides related to oxytocin ring moiety
    1980, Vol. 45, Issue 4, pp. 1109–1131 [Abstract]
  • Karel Hauzer, Tomislav Barth and Karel Jošt
    Activation of vasopressin hormonogens by kidney aminoacylarylamidase; Study in vitro
    1980, Vol. 45, Issue 3, pp. 772–776 [Abstract]
  • Jan Pospíšek, Štefan Toma, Ivo Frič and Karel Bláha
    The optically active 3-ferrocenylalanine and its application in peptide chemistry
    1980, Vol. 45, Issue 2, pp. 435–441 [Abstract]
  • Zdeněk Havlas and Petr Maloň
    Molecular geometries - Accuracy test of the PCILO method
    1980, Vol. 45, Issue 2, pp. 321–329 [Abstract]
  • Vera Bojanovska, Tomislav Barth, Bohuslav Černý, Karel Hauzer and Karel Jošt
    The preparation and metabolic fate of tritiated Nα-acetyl[2-O-methyltyrosine]oxytocin - An inhibitor of the uterotonic action of oxytocin
    1979, Vol. 44, Issue 9, pp. 2702–2709 [Abstract]
  • Miloš Tichý, Petr Maloň, Ivo Frič and Karel Bláha
    Synthesis and chiroptical properties of (-)-(1R)-3-azatricyclo[5,4,0,04,9]undecan-2-one - A lactam with non-planar cis-amide group
    1979, Vol. 44, Issue 9, pp. 2653–2659 [Abstract]
  • Michal Lebl, Vera Bojanovska, Tomislav Barth and Karel Jošt
    Synthesis and properties of oxytocin analogues acting as irreversible inhibitors of the uterotonic response to oxytocin
    1979, Vol. 44, Issue 8, pp. 2573–2582 [Abstract]
  • Michal Lebl, Tomislav Barth and Karel Jošt
    Analogues of oxytocin with esters of glutamic acid instead of glutamine in position 4: Synthesis of a compound with high and specific galactogogic activity
    1979, Vol. 44, Issue 8, pp. 2563–2572 [Abstract]
  • Michal Lebl, Anastasia Dimeli, Vera Bojanovska, Jiřina Slaninová, Tomislav Barth and Karel Jošt
    Synthesis and some biological properties of amides derived from [4-glutamic acid]deamino-1-carba-oxytocin
    1979, Vol. 44, Issue 8, pp. 2556–2562 [Abstract]
  • Anastasia Dimeli and Tomislav Barth
    Tryptic splitting of vasopressin analogues containing homologues of lysine or arginine in position 8
    1979, Vol. 44, Issue 8, pp. 2451–2454 [Abstract]
  • Milan Zaoral, Viktor Krchňák, František Brtník, Alena Machová and Jana Škopková
    [1-β-Mercaptopropionic acid, 8-α-amino-β-guanidinopropionic acid]vasopressin and [1-β-mercaptopropionic acid, 8-D-α-amino-β-guanidinopropionic acid]vasopressin; Analogs showing a high and specific antidiuretic effect
    1979, Vol. 44, Issue 8, pp. 2447–2450 [Abstract]
  • Asja Šiševa, Jiřina Slaninová, Tomislav Barth, Stephan P. Ditzov and Luben M. Sirakov
    Isoelectric focusing of insulin, 125I-insulin and the 125I-insulin-antibody complex
    1979, Vol. 44, Issue 6, pp. 1828–1834 [Abstract]
  • Petr Pančoška, Ivo Frič and Karel Bláha
    Statistical accuracy test in measurements of circular dichroism
    1979, Vol. 44, Issue 4, pp. 1312–1317 [Abstract]
  • Petr Pančoška, Ivo Frič and Karel Bláha
    Modified factor analysis of the circular dichroism spectra, applied to a series of cyclodipeptides containing L-proline
    1979, Vol. 44, Issue 4, pp. 1296–1311 [Abstract]
  • Milan Zaoral, František Brtník, Martin Flegel, Tomislav Barth and Alena Machová
    [1-β-Mercaptopropionic acid, 8-norarginine]vasopressin and [1-β-mercaptopropionic acid, 8-D-norarginine]vasopressin. Two analogs with strong biological effects
    1979, Vol. 44, Issue 4, pp. 1179–1186 [Abstract]
  • Jan Hlaváček, Tomislav Barth, Karel Bláha and Karel Jošt
    Synthesis of oxytocin analogues modified in the tripeptide side-chain by condensation of aminoterminal linear hexapeptide with the carboxyterminal tripeptide
    1979, Vol. 44, Issue 1, pp. 275–287 [Abstract]
  • Slavomír Bystrický, Ivo Frič, Jan Staněk, Karel Čapek, Jiří Jarý and Karel Bláha
    Conformation of 3-acetamido-3,6-dideoxyhexopyranosides: Circular dichroism study
    1979, Vol. 44, Issue 1, pp. 174–182 [Abstract]
  • Karel Bláha, Petr Maloň, Miloš Tichý, Ivo Frič, Ramakrishnan Usha, Suryanarayana Ramakumar and Kailasam Venkatesan
    Crystal structure and chiroptical properties of (+)-(3S)-4-azatricyclo[4,3,1,03,7]decan-5-one
    1978, Vol. 43, Issue 12, pp. 3241–3251 [Abstract]
  • Tomislav Barth, Asja Šiševa, Ljuben Sirakov, Jiřina Slaninová and Stefan Ditzov
    Cross-reaction of some insulin derivatives with anti-insulin serum
    1978, Vol. 43, Issue 11, pp. 2967–2972 [Abstract]
  • Michal Lebl, Tomislav Barth and Karel Jošt
    Synthesis, reduction, and pharmacological properties of the sulfoxides of some carba-analogues of oxytocin
    1978, Vol. 43, Issue 6, pp. 1538–1556 [Abstract]
  • Michal Lebl, Tomislav Barth and Karel Jošt
    Nα-Glycyl-glycyl-glycyl-8-ornithine-vasopressin: A trypsin resistant vasopressin analog with a specific pressor effect
    1978, Vol. 43, Issue 5, pp. 1300–1305 [Abstract]
  • Zdenko Procházka, Ivan Krejčí, Běla Kupková, Jiřina Slaninová, Vera Bojanovska, Zdeněk Prusík, Ilse A. Vosekalna, Petr Maloň, Tomislav Barth, Ivo Frič, Karel Bláha and Karel Jošt
    Synthesis and properties of the Nα-glycyl-glycyl-glycyl-8-lysine-vasopressin and its des-glycinamide derivative
    1978, Vol. 43, Issue 5, pp. 1285–1299 [Abstract]
  • Jiřina Slaninová, Tomislav Barth, Jana Škopková, Ivo Bláha and František Franěk
    Preparation of antibodies to [8-D-arginine]deamino-vasopressin and study of their cross-reactivity with vasopressin analogues
    1978, Vol. 43, Issue 4, pp. 1167–1174 [Abstract]
  • Petr Maloň, Slavomír Bystrický and Karel Bláha
    Semiempirical calculation of optical rotatory strength of non-planar conformations of formamide
    1978, Vol. 43, Issue 3, pp. 781–790 [Abstract]
  • Zdenko Procházka, Tomislav Barth, Joseph H. Cort, Karel Jošt and František Šorm
    Synthesis and some pharmacological properties of [8-L-arginine]deamino-1-carba-vasopressin
    1978, Vol. 43, Issue 2, pp. 655–663 [Abstract]
  • Michal Lebl and Karel Jošt
    Synthesis of [4-glutamic acid]deamino-1-carba-oxytocin
    1978, Vol. 43, Issue 2, pp. 523–534 [Abstract]
  • Milan Zaoral, Martin Flegel, Tomislav Barth and Alena Machová
    Purification of ten-grammes amounts of [1-β-mercaptopropionic acid, 8-D-arginine]vasopressin (DDAVP) on a continuous free-flow electrophoresis. Chemical and pharmacological data of DDAVP and by-products
    1978, Vol. 43, Issue 2, pp. 511–522 [Abstract]
  • Otakar Červinka and Petr Maloň
    Chiroptical properties of 1-(2-,3-,4-pyridyl)ethanols
    1978, Vol. 43, Issue 1, pp. 278–287 [Abstract]