Collect. Czech. Chem. Commun. 2009, 74, 1161-1178
https://doi.org/10.1135/cccc2009040
Published online 2009-07-24 10:06:36

Cytostatic tetrazole–butenolide conjugates: linking tetrazole and butenolide rings via stille coupling and biological activity of the target substances

Vojtěch Balšáneka, Lucie Tichotováb, Jiří Kunešb, Marcel Špulákb, Milan Pourb,*, Ivan Votrubac and Vladimír Buchtad

a RE&D VUFB Ltd., Poděbradská 56/186, 180 66 Prague 9, Czech Republic
b Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 03 Hradec Králové, Czech Republic
c Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
d Department of Clinical Microbiology, University Hospital, Sokolská 581, 500 05 Hradec Králové, Czech Republic

Individual author index pages


Other CCCC articles of these authors

  • Gabriel Birkuš, Ivan Votruba, Antonín Holý and Berta Otová
    HPMPApp as a substrate toward replicative DNA polymerases α, δ and ε
    Symposium Series 1999, Vol. 2, pp. 289–293 [Abstract]
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    Symposium Series 1999, Vol. 2, pp. 286–288 [Abstract]
    Published online 2016-05-08 23:32:58
  • Miroslav Otmar, Ivan Votruba and Antonín Holý
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    Symposium Series 1999, Vol. 2, pp. 252–254 [Abstract]
    Published online 2016-05-08 23:31:40
  • Michal Hocek, Martina Havelková, Dalimil Dvořák, Antonín Holý and Ivan Votruba
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    Symposium Series 1999, Vol. 2, pp. 27–30 [Abstract]
    Published online 2016-05-08 20:40:17
  • Miroslav Otmar, Milena Masojídková, Ivan Votruba and Antonín Holý
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    Symposium Series 2002, Vol. 5, pp. 38–39 [Abstract]
    Published online 2016-01-25 20:38:21
  • Markéta Schinkmanová, Ivan Votruba and Antonín Holý
    N6-methyl-AMP hydrolase activates N6-substituted purine ANPs
    Symposium Series 2005, Vol. 7, pp. 463–464 [Abstract]
    Published online 2015-11-08 11:58:20
  • Radim Nencka, Ivan Votruba, Hubert Hřebabecký, Eva Tloušťová, Květa Horská, Milena Masojídková and Antonín Holý
    Design and synthesis of 5,6-disubstituted uracil derivatives as potent inhibitors of thymidine phosphorylase
    Symposium Series 2005, Vol. 7, pp. 441–442 [Abstract]
    Published online 2015-11-08 11:57:40
  • Petr Kočalka, Markéta Rinnová, Václav Vaněk, Dominik Rejman, Ivan Votruba, Ivana Tomečková, Šárka Králíková, Magdalena Petrová, Ondřej Páv, Radek Pohl, Miloš Buděšínský, Radek Liboska, Zdeněk Točík and Ivan Rosenberg
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    Symposium Series 2005, Vol. 7, pp. 415–416 [Abstract]
    Published online 2015-11-08 11:56:57
  • Miroslav Hájek, Naděžda Matulová, Ivan Votruba, Antonín Holý and Eva Tloušťová
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    Symposium Series 2005, Vol. 7, pp. 373–374 [Abstract]
    Published online 2015-11-08 11:55:35
  • Peter Šilhár, Radek Pohl, Ivan Votruba and Michal Hocek
    Synthesis and transformations of 6-(hydroxymethyl)purines
    Symposium Series 2005, Vol. 7, pp. 221–224 [Abstract]
    Published online 2015-11-08 11:52:45
  • Ivan Rosenberg, Ivan Barvik, Miloš Buděšínský, Petr Kočalka, Šárka Králíková, Radek Liboska, Ondřej Pačes, Ondřej Páv, Magdalena Petrová, Radek Pohl, Martina Pressová, Dominik Rejman, Ivan Votruba and Zdeněk Točík
    Nucleoside phosphonic acids and related oligonucleotides: Structural diversity vs biological properties
    Symposium Series 2005, Vol. 7, pp. 153–157 [Abstract]
    Published online 2015-11-08 11:51:38
  • David Mařák, Miroslav Otmar, Martin Dračínský, Ivan Votruba and Antonín Holý
    Nucleosides and nucleotides containing 8-aza-7,9-dideazaxanthine
    Symposium Series 2008, Vol. 10, pp. 426–428 [Abstract]
    Published online 2015-10-30 18:44:11
  • Radim Nencka, Hubert Hřebabecký, Ivan Votruba, Martin Dračínský and Antonín Holý
    Metalation of 6-halo-2,4-dimethoxypyrimidines as the key step for the synthesis of biologicaly active compounds
    Symposium Series 2008, Vol. 10, pp. 249–253 [Abstract]
    Published online 2015-10-30 18:38:37
  • Karel Pomeisl, Antonín Holý, Ivan Votruba, Radim Nencka and Radek Pohl
    Facile syntheses of pyrimidine acyclic nucleoside phosphonates and their potential evaluation for biomedical applications
    Symposium Series 2008, Vol. 10, pp. 201–205 [Abstract]
    Published online 2015-10-30 18:37:39
  • Petr Jansa, Petr Špaček, Antonín Holý, Ivan Votruba and Zlatko Janeba
    Efficient one-pot synthesis of polysubstituted 6-[(1H-1,2,3-triazol-1-yl)methyl]uracils through the "click" protocol
    Symposium Series 2011, Vol. 12, pp. 467–468 [Abstract]
    Published online 2015-08-20 10:24:43
  • Martin Křováček, Hana Dvořáková, Ivan Votruba, Ivana Císařová and Dalimil Dvořák*
    6-Alkynylpurines bearing electronacceptor substituents: Preparation, reactivity in cycloaddition reactions and cytostatic activity
    2011, Vol. 76, Issue 12, pp. 1487–1527 [Abstract]
  • Petr Jansa*, Petr Špaček, Ivan Votruba, Petra Břehová, Martin Dračínský, Blanka Klepetářová and Zlatko Janeba
    Efficient one-pot synthesis of polysubstituted 6-[(1H-1,2,3-triazol-1-yl)methyl]uracils through the “click” protocol
    2011, Vol. 76, Issue 9, pp. 1121–1131 [Abstract]
  • Ivan Votruba*, Jana Trýznová, Petra Břehová, Eva Tloušťová, Květoslava Horská, Jindřich Fanfrlík, Ondřej Přenosil and Antonín Holý
    Inhibition of human purine nucleoside phosphorylase by tenofovir phosphate congeners
    2010, Vol. 75, Issue 12, pp. 1249–1257 [Abstract]
  • Markéta Schinkmanová*, Ivan Votruba, Riri Shibata, Bin Han, Xiaohong Liu, Tomas Cihlar and Antonín Holý
    Human N6-Methyl-AMP/DAMP Aminohydrolase (Abacavir 5'-Monophosphate Deaminase) is Capable of Metabolizing N6-Substituted Purine Acyclic Nucleoside Phosphonates
    2008, Vol. 73, Issue 2, pp. 275–291 [Abstract]
  • Marta Kučerová-Chlupáčová, Veronika Opletalová*, Josef Jampílek, Jan Doležel, Jiří Dohnal, Milan Pour, Jiří Kuneš and Viktor Voříšek
    New Hydrophobicity Constants of Substituents in Pyrazine Rings Derived from RP-HPLC Study
    2008, Vol. 73, Issue 1, pp. 1–18 [Abstract]
  • Ivan Šnajdr, Jan Pavlík, Radan Schiller, Jiří Kuneš and Milan Pour*
    Pentenolide Analogues of Antifungal Butenolides: Strategies Towards 3,6-Disubstituted Pyranones and Unexpected Loss of Biological Effect
    2007, Vol. 72, Issue 11, pp. 1472–1498 [Abstract]
  • Peter Šilhár, Radek Pohl, Ivan Votruba, Blanka Klepetářová and Michal Hocek*
    Synthesis of 6-Amino-, 6-Methyl- and 6-Aryl-2-(hydroxymethyl)purine Bases and Nucleosides
    2006, Vol. 71, Issue 6, pp. 788–803 [Abstract]
  • Karel Pomeisl*, Ivan Votruba, Antonín Holý and Radek Pohl
    Syntheses of Base and Side-Chain Modified Pyrimidine 1-[2-(Phosphonomethoxy)propyl] Derivatives as Potent Inhibitors of Thymidine Phosphorylase (PD-ECGF) from SD-Lymphoma
    2006, Vol. 71, Issue 4, pp. 595–624 [Abstract]
  • Veronika Opletalová*, Milan Pour, Jiří Kuneš, Vladimír Buchta, Luís Silva, Katarína Kráľová, Marta Chlupáčová, Dana Meltrová, Milan Peterka and Martina Posledníková
    Synthesis and Biological Evaluation of (E)-3-(Nitrophenyl)-1-(pyrazin-2-yl)prop-2-en-1-ones
    2006, Vol. 71, Issue 1, pp. 44–58 [Abstract]
  • Květoslava Horská, Ivan Votruba* and Antonín Holý
    Interaction of Phosphates of the Acyclic Nucleoside Phosphonates with Nucleoside Diphosphate Kinase from Yeast and Bovine Liver
    2006, Vol. 71, Issue 1, pp. 35–43 [Abstract]
  • Peter Šilhár, Radek Pohl, Ivan Votruba and Michal Hocek*
    Synthesis of 2-Substituted 6-(Hydroxymethyl)purine Bases and Nucleosides
    2005, Vol. 70, Issue 10, pp. 1669–1695 [Abstract]
  • Karel Pomeisl*, Radek Pohl, Antonín Holý and Ivan Votruba
    Simple Transformation of Thymine 1-[3-Hydroxy-2-(phosphonomethoxy)propyl] Derivatives to Their 1-[3-Fluoro-2-(phosphonomethoxy)propyl] Counterparts
    2005, Vol. 70, Issue 9, pp. 1465–1481 [Abstract]
  • Pavel Turek, Martin Kotora*, Michal Hocek* and Ivan Votruba
    Novel Method for Preparation of Highly Substituted 6-Arylpurines by Reactions of 6-Alkynylpurines with Zirconacyclopentadienes
    2005, Vol. 70, Issue 3, pp. 339–349 [Abstract]
  • Petr Nauš, Ivan Votruba and Michal Hocek*
    Covalent Analogues of DNA Base-Pairs and Triplets VII. Synthesis and Cytostatic Activity of Bis(purin-6-yl)acetylene and -diacetylene Nucleosides
    2004, Vol. 69, Issue 10, pp. 1955–1970 [Abstract]
  • Alois Pískala*, Naeem B. Hanna, Milena Masojídková, Pavel Fiedler and Ivan Votruba
    Synthesis of N4-Amino and N4-Hydroxy Derivatives of 5-Azacytidine. A Facile Rearrangement of the N4-Amino Derivative to 5-(3-β-D-Ribofuranosylureido)-1H-1,2,4-triazole
    2004, Vol. 69, Issue 4, pp. 905–917 [Abstract]
  • Petr Čapek, Miroslav Otmar*, Milena Masojídková, Ivan Votruba and Antonín Holý
    A Facile Synthesis of 9-Deaza Analogue of Olomoucine
    2003, Vol. 68, Issue 4, pp. 779–791 [Abstract]
  • Jiří Kuneš, Vojtěch Balšánek, Milan Pour* and Vladimír Buchta
    Synthesis and Antifungal Activity Evaluation of 3-Hetaryl-2,5-dihydrofuran-2-ones. An Unusual Fragmentation of the Oxazole Ring via 2,3-Selenoxide Shift
    2001, Vol. 66, Issue 12, pp. 1809–1830 [Abstract]
  • Gabriel Birkuš, Ivan Votruba*, Miroslav Otmar and Antonín Holý
    Interactions of 1-[(S)-3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine (Cidofovir) Diphosphate with DNA Polymerases α, δ and ε*
    2001, Vol. 66, Issue 11, pp. 1698–1706 [Abstract]
  • Antonín Holý*, Ivan Votruba, Eva Tloušťová and Milena Masojídková
    Synthesis and Cytostatic Activity of N-[2-(Phosphonomethoxy)alkyl] Derivatives of N6-Substituted Adenines, 2,6-Diaminopurines and Related Compounds
    2001, Vol. 66, Issue 10, pp. 1545–1592 [Abstract]
  • Miroslav Otmar*, Milena Masojídková, Ivan Votruba and Antonín Holý
    An Alternative Synthesis of HPMPC and HPMPA Diphosphoryl Derivatives
    2001, Vol. 66, Issue 3, pp. 500–506 [Abstract]
  • Michal Hocek*, Antonín Holý, Ivan Votruba and Hana Dvořáková
    Cytostatic 6-Arylpurine Nucleosides III. Synthesis and Structure-Activity Relationship Study in Cytostatic Activity of 6-Aryl-, 6-Hetaryl- and 6-Benzylpurine Ribonucleosides
    2001, Vol. 66, Issue 3, pp. 483–499 [Abstract]
  • Michal Hocek*, Antonín Holý, Ivan Votruba and Hana Dvořáková
    Cytostatic 6-Arylpurine Nucleosides II. Synthesis of Sugar-Modified Derivatives: 9-(2-Deoxy-β-D-erythro-pentofuranosyl)-, 9-(5-Deoxy-β-D-ribofuranosyl)- and 9-(2,3-Dihydroxypropyl)-6-phenylpurines
    2000, Vol. 65, Issue 11, pp. 1683–1697 [Abstract]
  • Romana Krejčová, Květoslava Horská, Ivan Votruba* and Antonín Holý
    Phosphorylation of Purine (Phosphonomethoxy)alkyl Derivatives by Mitochondrial AMP Kinase (AK2 Type) from L1210 Cells
    2000, Vol. 65, Issue 10, pp. 1653–1668 [Abstract]
  • Karel Waisser*, Miloš Macháček, Hynek Dostál, Jiří Gregor, Lenka Kubicová, Věra Klimešová, Jiří Kuneš, Karel Palát, Jr., Jana Hladůvková, Jarmila Kaustová and Ute Möllmann
    Relationships Between the Chemical Structure of Substances and Their Antimycobacterial Activity Against Atypical Strains. Part 18. 3-Phenyl-2H-1,3-benzoxazine-2,4(3H)-diones and Isosteric 3-Phenylquinazoline-2,4(1H,3H)-diones
    1999, Vol. 64, Issue 11, pp. 1902–1924 [Abstract]
  • Romana Krejčová, Květoslava Horská, Ivan Votruba* and Antonín Holý
    Isoenzymes of GMP Kinase from L1210 Cells: Isolation and Characterization
    1999, Vol. 64, Issue 3, pp. 559–570 [Abstract]
  • Věra Klimešová*, Martin Svoboda, Karel Waisser, Milan Pour and Jarmila Kaustová
    Synthesis and Antimicrobial Activity of New 4-(Benzylsulfanyl)pyridine Derivatives
    1999, Vol. 64, Issue 2, pp. 417–434 [Abstract]
  • Gabriel Birkuš, Pavel Kramata, Ivan Votruba, Berta Otová, Miroslav Otmar and Antonín Holý
    Nonproteolyzed Form of DNA-Polymerase ε from T-Cell Spontaneous Lymphoma of Sprague-Dawley Inbred Rat: Isolation and Characterization
    1998, Vol. 63, Issue 5, pp. 723–731 [Abstract]
  • Jiří Kuneš, Jiří Jáchym, Petr Jirásko, Želmíra Odlerová and Karel Waisser
    Combination of the Topliss Approach with the Free-Wilson Analysis in the Study of Antimycobacterial Activityof 4-Alkylthiobenzanilides
    1997, Vol. 62, Issue 9, pp. 1503–1510 [Abstract]
  • Lenka Olšanská, Tomas Cihlar, Ivan Votruba* and Antonín Holý
    Transport of Adefovir (PMEA) in Human T-Lymphoblastoid Cells
    1997, Vol. 62, Issue 5, pp. 821–828 [Abstract]
  • Pavel Kramata, Gabriel Birkuš, Miroslav Otmar, Ivan Votruba and Antonín Holý
    Structural features of acyclic nucleotide analogs conferring inhibitory effects on cellular replicative DNA polymerases
    1996, Vol. 61, Special Issue, pp. S188–S191 [Abstract]
  • Antonín Holý, Zdeněk Zídek and Ivan Votruba
    Inhibition of murine lymphocyte proliferation by N6-substituted acyclic purine nucleoside phosphonates
    1996, Vol. 61, Special Issue, pp. S182–S187 [Abstract]
  • Romana Krejčová, Květoslava Horská, Ivan Votruba and Antonín Holý
    Phosphorylation of phosphonomethoxyalkylguanines by GMP-kinase isoenzymes
    1996, Vol. 61, Special Issue, pp. S134–S136 [Abstract]
  • Martin Doležal, Jiří Hartl, Antonín Lyčka, Vladimír Buchta and Želmíra Odlerová
    Synthesis and Antituberculotic Properties of Some Substituted Pyrazinecarbothioamides
    1996, Vol. 61, Issue 7, pp. 1102–1108 [Abstract]
  • Karel Waisser, Jiří Kuneš, Alexandr Hrabálek, Miloš Macháček and Želmíra Odlerová
    New Groups of Potential Antituberculotics: 5-Alkylthio-1-aryltetrazoles
    1996, Vol. 61, Issue 5, pp. 791–798 [Abstract]
  • Pavel Kramata, Jaroslav Černý, Gabriel Birkuš, Ivan Votruba, Berta Otová and Antonín Holý
    DNA-Polymerases α, δ and ε from T-Cell Spontaneous Lymphoblastic Leukemia of Sprague-Dawley Inbred Rat: Isolation and Characterization
    1995, Vol. 60, Issue 9, pp. 1555–1572 [Abstract]
  • Martin Doležal, Jiří Hartl, Antonín Lyčka, Vladimír Buchta and Želmíra Odlerová
    Synthesis and Antituberculotic Activity of Some Substituted 3-Arylamino-5-cyano-2-pyrazinecarboxamides
    1995, Vol. 60, Issue 7, pp. 1236–1241 [Abstract]
  • Ivan Votruba, Antonín Holý, Hana Dvořáková, Jaroslav Günter, Dana Hocková, Hubert Hřebabecký, Tomas Cihlar and Milena Masojídková
    Synthesis of 2-Deoxy-β-D-ribonucleosides and 2,3-Dideoxy-β-D-pentofuranosides on Immobilized Bacterial Cells
    1994, Vol. 59, Issue 10, pp. 2303–2330 [Abstract]
  • Karel Waisser, Jiří Kuneš, Alexandr Hrabálek and Želmíra Odlerová
    New Groups of Potential Antituberculotics: Bis(1-aryltetrazol-5-yl) Disulfides. Structure Activity Relationship
    1994, Vol. 59, Issue 1, pp. 234–238 [Abstract]
  • Hana Dvořáková, Antonín Holý, Ivan Votruba and Milena Masojídková
    Synthesis and Biological Effects of Acyclic Analogs of Deazapurine Nucleosides
    1993, Vol. 58, Issue 3, pp. 629–648 [Abstract]
  • Karel Waisser, Jiří Kuneš, Jiří Klimeš, Miroslav Polášek and Želmíra Odlerová
    Relations between Structure and Antituberculotic Activity of 4-Alkoxybenzoic Acids
    1993, Vol. 58, Issue 1, pp. 191–196 [Abstract]
  • Pavel Kramata and Ivan Votruba
    Enzymes of Human Herpesviruses
    1992, Vol. 57, Issue 8, pp. 1577–1612 [Abstract]
  • Tomas Cihlar, Ivan Votruba, Květoslava Horská, Radek Liboska, Ivan Rosenberg and Antonín Holý
    Metabolism of 1-(S)-(3-Hydroxy-2-phosphonomethoxypropyl)cytosine (HPMPC) in Human Embryonic Lung Cells
    1992, Vol. 57, Issue 3, pp. 661–672 [Abstract]
  • Karel Waisser, Jiří Kuneš and Želmíra Odlerová
    Correlation of structural parameters with antituberculotic activity in a group of 2-benzamidobenzothiazoles
    1991, Vol. 56, Issue 12, pp. 2978–2985 [Abstract]
  • Katarina Šedivá, Ivan Votruba, Antonín Holý and Ivan Rosenberg
    Purine nucleoside phosphorylase: Isolation and characterization
    1990, Vol. 55, Issue 12, pp. 2987–2999 [Abstract]
  • Antonín Holý, Masahiko Nishizawa, Ivan Rosenberg and Ivan Votruba
    The effect of phosphonylmethyl analogs of ribonucleoside 5'-diphosphates on (E. coli) polynucleotide phosphorylase catalyzed reactions
    1987, Vol. 52, Issue 12, pp. 3042–3057 [Abstract]
  • Antonín Holý, Joachim König, Jiří Veselý, Dieter Cech, Ivan Votruba and Erik De Clercq
    5'-O-Alkyl-5-fluorouridines: Synthesis and biological activity
    1987, Vol. 52, Issue 6, pp. 1589–1608 [Abstract]
  • Antonín Holý, Jitka Kohoutová, Aleš Merta and Ivan Votruba
    9-(Aminoalkyl)-8-hydroxyadenines: Preparation, mechanism of formation and use in affinity chromatography of S-adenosyl-L-homocysteine hydrolase
    1986, Vol. 51, Issue 2, pp. 459–477 [Abstract]
  • Antonín Holý, Anita Ludziša, Ivan Votruba, Kateřina Šedivá and Helmut Pischel
    Preparation of analogues of cytosine and 2-pyrimidinone nucleosides and their effect on bacterial (Escherichia coli A 19) cytidine aminohydrolase
    1985, Vol. 50, Issue 2, pp. 393–417 [Abstract]
  • Antonín Holý, Ivan Votruba and Erik De Clercq
    Structure-activity studies on open-chain analogues of nucleosides: Inhibition of S-adenosyl-L-homocysteine hydrolase and antiviral activity 2. Acid open-chain analogues
    1985, Vol. 50, Issue 1, pp. 262–279 [Abstract]
  • Antonín Holý, Ivan Votruba and Erik De Clercq
    Structure-activity studies on open-chain analogues of nucleosides: Inhibition of S-adenosyl-L-homocysteine hydrolase and antiviral activity 1. Neutral open-chain analogues
    1985, Vol. 50, Issue 1, pp. 245–261 [Abstract]
  • Ladislava Šebestová, Ivan Votruba and Antonín Holý
    S-adenosine-L-homocysteine hydrolase from Nicotiana tabacum L.: Isolation and properties
    1984, Vol. 49, Issue 6, pp. 1543–1551 [Abstract]
  • Aleš Merta, Ivan Votruba, Jiří Veselý and Antonín Holý
    S-adenosyl-L-homocysteine hydrolase from mouse leukemic cells: Isolation and properties
    1983, Vol. 48, Issue 9, pp. 2701–2708 [Abstract]
  • Ivan Votruba, Antonín Holý and Ivan Rosenberg
    Affinity chromatography of rat liver S-adenosyl-L-homocysteine hydrolase
    1983, Vol. 48, Issue 9, pp. 2549–2557 [Abstract]
  • Antonín Holý, Ivan Votruba and Erik De Clercq
    Synthesis and antiviral activity of stereoisomeric eritadenines
    1982, Vol. 47, Issue 5, pp. 1392–1407 [Abstract]
  • Ivan Votruba and Antonín Holý
    Eritadenines - Novel type of potent inhibitors of S-adenosyl-L-homocysteine hydrolase
    1982, Vol. 47, Issue 1, pp. 167–172 [Abstract]
  • Ivan Votruba and Antonín Holý
    Inhibition of S-adenosyl-L-homocysteine hydrolase by the aliphatic nucleoside analogue - 9-(S)-(2,3-dihydroxypropyl)adenine
    1980, Vol. 45, Issue 11, pp. 3039–3044 [Abstract]