Crossref Cited-by Linking logo

Collect. Czech. Chem. Commun. 2001, 66, 1545-1592
https://doi.org/10.1135/cccc20011545

Synthesis and Cytostatic Activity of N-[2-(Phosphonomethoxy)alkyl] Derivatives of N6-Substituted Adenines, 2,6-Diaminopurines and Related Compounds

Antonín Holý*, Ivan Votruba, Eva Tloušťová and Milena Masojídková

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

Crossref Cited-by Linking

  • Krečmerová Marcela, Majer Pavel, Rais Rana, Slusher Barbara S.: Phosphonates and Phosphonate Prodrugs in Medicinal Chemistry: Past Successes and Future Prospects. Front. Chem. 2022, 10. <https://doi.org/10.3389/fchem.2022.889737>
  • Ghaem Maghami Mohammad, Dey Surjendu, Lenz Ann‐Kathrin, Höbartner Claudia: Repurposing Antiviral Drugs for Orthogonal RNA‐Catalyzed Labeling of RNA. Angewandte Chemie 2020, 132, 9421. <https://doi.org/10.1002/ange.202001300>
  • Ghaem Maghami Mohammad, Dey Surjendu, Lenz Ann‐Kathrin, Höbartner Claudia: Repurposing Antiviral Drugs for Orthogonal RNA‐Catalyzed Labeling of RNA. Angew Chem Int Ed 2020, 59, 9335. <https://doi.org/10.1002/anie.202001300>
  • Klejch Tomáš, Pohl Radek, Janeba Zlatko, Sun Minghan, Keough Dianne T., Guddat Luke W., Hocková Dana: Acyclic nucleoside phosphonates with unnatural nucleobases, favipiravir and allopurinol, designed as potential inhibitors of the human and Plasmodium falciparum 6-oxopurine phosphoribosyltransferases. Tetrahedron 2018, 74, 5886. <https://doi.org/10.1016/j.tet.2018.08.014>
  • Baszczyňski Ondřej, Kaiser Martin Maxmilian, Česnek Michal, Břehová Petra, Jansa Petr, Procházková Eliška, Dračínský Martin, Snoeck Robert, Andrei Graciela, Janeba Zlatko: Xanthine-based acyclic nucleoside phosphonates with potent antiviral activity against varicella-zoster virus and human cytomegalovirus. Antivir Chem Chemother 2018, 26, 204020661881305. <https://doi.org/10.1177/2040206618813050>
  • Šimůnková Naděžda, Tobrman Tomáš, Eigner Václav, Dvořák Dalimil: A Study on the Intramolecular Mitsunobu Reaction of N6‐(ω‐Hydroxyalkyl)adenines. Journal of Heterocyclic Chem 2017, 54, 3565. <https://doi.org/10.1002/jhet.2982>
  • Bessières Maxime, Sari Ozkan, Roy Vincent, Warszycki Dawid, Bojarski Andrzej J., Nolan Steven P., Snoeck Robert, Andrei Graciela, Schinazi Raymond F., Agrofoglio Luigi A.: Sonication-Assisted Synthesis of (E) -2-Methyl-but-2-enyl Nucleoside Phosphonate Prodrugs. ChemistrySelect 2016, 1, 3108. <https://doi.org/10.1002/slct.201600879>
  • Špak Josef, Janeba Zlatko, Jansa Petr, Baszczyňski Ondřej, Pavingerová Daniela, Špaková Vlastimila: Phytotoxicity of acyclic nucleoside phosphonates in Brassica pekinensis and Solanum lycopersicum. Plant Cell Tiss Organ Cult 2016, 125, 375. <https://doi.org/10.1007/s11240-016-0942-4>
  • Eletskaya Barbara Z., Konstantinova Irina D., Paramonov Alexander S., Esipov Roman S., Gruzdev Dmitry A., Vigorov Alexey Yu., Levit Galina L., Miroshnikov Anatoly I., Krasnov Victor P., Charushin Valery N.: Chemoenzymatic arabinosylation of 2-aminopurines bearing the chiral fragment of 7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazines. Mendeleev Communications 2016, 26, 6. <https://doi.org/10.1016/j.mencom.2016.01.003>
  • Zouharova Darina, Lipenska Ivana, Fojtikova Martina, Kulich Pavel, Neca Jiri, Slany Michal, Kovarcik Kamil, Turanek-Knotigova Pavlina, Hubatka Frantisek, Celechovska Hana, Masek Josef, Koudelka Stepan, Prochazka Lubomir, Eyer Ludek, Plockova Jana, Bartheldyova Eliska, Miller Andrew D., Ruzek Daniel, Raska Milan, Janeba Zlatko, Turanek Jaroslav: Antiviral activities of 2,6-diaminopurine-based acyclic nucleoside phosphonates against herpesviruses: In vitro study results with pseudorabies virus (PrV, SuHV-1). Veterinary Microbiology 2016, 184, 84. <https://doi.org/10.1016/j.vetmic.2016.01.010>
  • Krasnov V. P., Vigorov A. Yu., Gruzdev D. A., Levit G. L., Demin A. M., Nizova I. A., Tumashov A. A., Sadretdinova L. Sh., Gorbunov E. B., Charushin V. N.: Synthesis of enantiomers of N-(2-aminopurin-6-yl)amino acids. Russ Chem Bull 2015, 64, 2106. <https://doi.org/10.1007/s11172-015-1125-x>
  • Krasnov Victor P., Gruzdev Dmitry A., Chulakov Evgeny N., Vigorov Alexey Yu., Musiyak Vera V., Matveeva Tatyana V., Tumashov Andrey A., Levit Galina L., Charushin Valery N.: Synthesis of novel purin-6-yl conjugates with heterocyclic amines linked via 6-aminohexanoyl fragment. Mendeleev Communications 2015, 25, 412. <https://doi.org/10.1016/j.mencom.2015.11.003>
  • Vigorov Alexey Yu., Krasnov Viktor P., Gruzdev Dmitry A., Men'shikova Alisa A., Demin Alexander M., Levit Galina L., Charushin Valery N.: Novel synthetic routes to N-(2-amino-9H-purin-6-yl)-substituted amino acids. Mendeleev Communications 2014, 24, 35. <https://doi.org/10.1016/j.mencom.2013.12.011>
  • Xie Ming-Sheng, Niu Hong-Ying, Qu Gui-Rong, Guo Hai-Ming: The development for the synthesis of chiral acyclic nucleosides and their phosphonates. Tetrahedron Letters 2014, 55, 7156. <https://doi.org/10.1016/j.tetlet.2014.11.060>
  • Zhang Qian, Ma Bai-Wei, Wang Qian-Qian, Wang Xing-Xing, Hu Xia, Xie Ming-Sheng, Qu Gui-Rong, Guo Hai-Ming: The Synthesis of Tenofovir and Its Analogues via Asymmetric Transfer Hydrogenation. Org. Lett. 2014, 16, 2014. <https://doi.org/10.1021/ol500583d>
  • Mudryk Boguslaw, Zheng Bin, Chen Ke, Eastgate Martin D.: Development of a Robust Process for the Preparation of High-Quality Dicyclopropylamine Hydrochloride. Org. Process Res. Dev. 2014, 18, 520. <https://doi.org/10.1021/op500031z>
  • Gómez-Coca Raquel B., Sigel Astrid, Operschall Bert P., Holý Antonín, Sigel Helmut: Solution properties of metal ion complexes formed with the antiviral and cytostatic nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]-2-amino-6-dimethylaminopurine (PME2A6DMAP). Can. J. Chem. 2014, 92, 771. <https://doi.org/10.1139/cjc-2014-0041>
  • Głowacka Iwona E., Balzarini Jan, Wróblewski Andrzej E.: Synthesis and Biological Evaluation of Novel 1,2,3‐Triazolonucleotides. Archiv der Pharmazie 2013, 346, 278. <https://doi.org/10.1002/ardp.201200421>
  • Roux Loïc, Priet Stéphane, Payrot Nadine, Weck Clément, Fournier Maëlenn, Zoulim Fabien, Balzarini Jan, Canard Bruno, Alvarez Karine: Ester prodrugs of acyclic nucleoside thiophosphonates compared to phosphonates: Synthesis, antiviral activity and decomposition study. European Journal of Medicinal Chemistry 2013, 63, 869. <https://doi.org/10.1016/j.ejmech.2013.02.039>
  • Mandíková Jana, Volková Marie, Pávek Petr, Česnek Michal, Janeba Zlatko, Kubíček Vladimír, Trejtnar František: Interactions with selected drug renal transporters and transporter-mediated cytotoxicity in antiviral agents from the group of acyclic nucleoside phosphonates. Toxicology 2013, 311, 135. <https://doi.org/10.1016/j.tox.2013.07.004>
  • Gómez‐Coca Raquel B., Blindauer Claudia A., Sigel Astrid, Operschall Bert P., Holý Antonín, Sigel Helmut: Extent of Intramolecular π‐Stacks in Aqueous Solution in Mixed‐Ligand Copper(II) Complexes Formed by Heteroaromatic Amines and Several 2‐Aminopurine Derivatives of the Antivirally Active Nucleotide Analog 9‐[2‐(Phosphonomethoxy)ethyl]adenine (PMEA). Chemistry & Biodiversity 2012, 9, 2008. <https://doi.org/10.1002/cbdv.201200022>
  • Pradère Ugo, Roy Vincent, Montagu Aurélien, Sari Ozkan, Hamada Manabu, Balzarini Jan, Snoeck Robert, Andrei Graciela, Agrofoglio Luigi A.: Synthesis and antiviral evaluation of bis(POM) prodrugs of (E)-[4′-phosphono-but-2′-en-1′-yl]purine nucleosides. European Journal of Medicinal Chemistry 2012, 57, 126. <https://doi.org/10.1016/j.ejmech.2012.08.042>
  • Kostecká Petra, Holý Antonín, Farghali Hassan, Zídek Zdeněk, Kmoníčková Eva: Differential effects of acyclic nucleoside phosphonates on nitric oxide and cytokines in rat hepatocytes and macrophages. International Immunopharmacology 2012, 12, 342. <https://doi.org/10.1016/j.intimp.2011.12.005>
  • Kaiser Martin Maxmilian, Jansa Petr, Dračínský Martin, Janeba Zlatko: A novel type of acyclic nucleoside phosphonates derived from 2-(phosphonomethoxy)propanoic acid. Tetrahedron 2012, 68, 4003. <https://doi.org/10.1016/j.tet.2012.03.066>
  • Vávrová Kateřina, Kovaříková Petra, Školová Barbora, Líbalová Martina, Roh Jaroslav, Čáp Robert, Holý Antonín, Hrabálek Alexandr: Enhanced Topical and Transdermal Delivery of Antineoplastic and Antiviral Acyclic Nucleoside Phosphonate cPr-PMEDAP. PHARMA RES 2011, 28, 3105. <https://doi.org/10.1007/s11095-011-0508-4>
  • Špak Josef, Votruba Ivan, Pavingerová Daniela, Holý Antonín, Špaková Vlastimila, Petrzik Karel: Antiviral activity of tenofovir against Cauliflower mosaic virus and its metabolism in Brassica pekinensis plants. Antiv Res 2011, 92, 378. <https://doi.org/10.1016/j.antiviral.2011.08.014>
  • Baszczyňski Ondřej, Jansa Petr, Dračínský Martin, Klepetářová Blanka, Holý Antonín, Votruba Ivan, Clercq Erik de, Balzarini Jan, Janeba Zlatko: Synthesis and antiviral activity of N9-[3-fluoro-2-(phosphonomethoxy)propyl] analogues derived from N6-substituted adenines and 2,6-diaminopurines. Bioorganic & Medicinal Chemistry 2011, 19, 2114. <https://doi.org/10.1016/j.bmc.2011.02.050>
  • Jansa Petr, Baszczyňski Ondřej, Dračínský Martin, Votruba Ivan, Zídek Zdeněk, Bahador Gina, Stepan George, Cihlar Tomas, Mackman Richard, Holý Antonín: A novel and efficient one-pot synthesis of symmetrical diamide (bis-amidate) prodrugs of acyclic nucleoside phosphonates and evaluation of their biological activities. Eur Med Chem 2011, 46, 3748. <https://doi.org/10.1016/j.ejmech.2011.05.040>
  • Barral Karine, Weck Clément, Payrot Nadine, Roux Loic, Durafour Céline, Zoulim Fabien, Neyts Johan, Balzarini Jan, Canard Bruno, Priet Stéphane: Acyclic nucleoside thiophosphonates as potent inhibitors of HIV and HBV replication. Eur Med Chem 2011, 46, 4281. <https://doi.org/10.1016/j.ejmech.2011.06.034>
  • Čechová Lucie, Jansa Petr, Šála Michal, Dračínský Martin, Holý Antonín, Janeba Zlatko: The optimized microwave-assisted decomposition of formamides and its synthetic utility in the amination reactions of purines. Tetrahedron 2011, 67, 866. <https://doi.org/10.1016/j.tet.2010.12.040>
  • Kundarapu Maheshwar, Marchand Damien, Dumbre Shrinivas G., Herdewijn Piet: Synthesis of new acyclic nucleoside phosphonates (ANPs) substituted on the 1′ and/or 2′ positions. Tetrahedron Letters 2011, 52, 6896. <https://doi.org/10.1016/j.tetlet.2011.10.037>
  • Sedláček Ondřej, Břehová Petra, Pohl Radek, Holý Antonín, Janeba Zlatko: The synthesis of the 8-C-substituted 2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine (PMEDAP) derivatives by diverse cross-coupling reactions. Can. J. Chem. 2011, 89, 488. <https://doi.org/10.1139/V11-001>
  • Zink Charles N., Soissons Nicolas, Fishbein James C.: Products of the Direct Reaction of the Diazonium Ion of a Metabolite of the Carcinogen N-Nitrosomorpholine with Purines of Nucleosides and DNA. Chem. Res. Toxicol. 2010, 23, 1223. <https://doi.org/10.1021/tx100093a>
  • De Clercq Erik: Antiviral drug discovery: Ten more compounds, and ten more stories (part B). Medicinal Research Reviews 2009, 29, 571. <https://doi.org/10.1002/med.20149>
  • Borrmann Thomas, Abdelrahman Aliaa, Volpini Rosaria, Lambertucci Catia, Alksnis Edgars, Gorzalka Simone, Knospe Melanie, Schiedel Anke C., Cristalli Gloria, Müller Christa E.: Structure−Activity Relationships of Adenine and Deazaadenine Derivatives as Ligands for Adenine Receptors, a New Purinergic Receptor Family. J. Med. Chem. 2009, 52, 5974. <https://doi.org/10.1021/jm9006356>
  • Česnek Michal, Holý Antonín, Masojídková Milena, Kmoníčková Eva, Zídek Zdeněk: Synthesis of guanidino analogues of PMPDAP and their immunobiological activity. biorg med chem 2008, 16, 965. <https://doi.org/10.1016/j.bmc.2007.10.010>
  • Schinkmanová Markéta, Votruba Ivan, Shibata Riri, Han Bin, Liu Xiaohong, Cihlar Tomas, Holý Antonín: Human N6-Methyl-AMP/DAMP Aminohydrolase (Abacavir 5'-Monophosphate Deaminase) is Capable of Metabolizing N6-Substituted Purine Acyclic Nucleoside Phosphonates. Collect. Czech. Chem. Commun. 2008, 73, 275. <https://doi.org/10.1135/cccc20080275>
  • Potměšil Petr, Holý Antonín, Kmoníčková Eva, Křížková Jana, Zídek Zdeněk: Acyclic nucleoside phosphonate antivirals activate gene expression of monocyte chemotactic protein 1 and 3. J Biomed Sci 2007, 14, 59. <https://doi.org/10.1007/s11373-006-9116-4>
  • Zídek Zdeněk, Kmoníčková Eva, Holý Antonín: Secretion of antiretroviral chemokines by human cells cultured with acyclic nucleoside phosphonates. EUROP J PHARMACOL 2007, 574, 77. <https://doi.org/10.1016/j.ejphar.2007.07.024>
  • Kmoníčková Eva, Melkusová Petra, Farghali Hassan, Holý Antonín, Zídek Zdeněk: Nitric oxide production in mouse and rat macrophages: A rapid and efficient assay for screening of drugs immunostimulatory effects in human cells. Nitric Oxide-Biology and Chemistry 2007, 17, 160. <https://doi.org/10.1016/j.niox.2007.06.006>
  • Schinkmanová Markéta, Votruba Ivan, Holý Antonín: N6-Methyl-AMP aminohydrolase activates N6-substituted purine acyclic nucleoside phosphonates. Biochemical Pharmacology 2006, 71, 1370. <https://doi.org/10.1016/j.bcp.2006.01.013>
  • Hořejší Kateřina, Andrei Graciela, Clercq Erik De, Snoeck Robert, Pohl Radek, Holý Antonín: Tricyclic etheno analogs of PMEG and PMEDAP: Synthesis and biological activity. Bioorganic & Medicinal Chemistry 2006, 14, 8057. <https://doi.org/10.1016/j.bmc.2006.07.036>
  • Kmoníčková Eva, Potměšil Petr, Holý Antonín, Zídek Zdeněk: Purine P1 receptor-dependent immunostimulatory effects of antiviral acyclic analogues of adenine and 2,6-diaminopurine. EUROP J PHARMACOL 2006, 530, 179. <https://doi.org/10.1016/j.ejphar.2005.11.037>
  • Hořejší Kateřina, Pohl Radek, Holý Antonín: Tricyclic Purine Analogs Derived from 2-Amino-6-chloropurine and 2,6-Diaminopurine and Their Methylated Quaternary Salts. Collect. Czech. Chem. Commun. 2006, 71, 77. <https://doi.org/10.1135/cccc20060077>
  • Krečmerová Marcela, Masojídková Milena, Holý Antonín: Preparation of C-5 Substituted Cidofovir Derivatives. Collect. Czech. Chem. Commun. 2006, 71, 579. <https://doi.org/10.1135/cccc20060579>
  • Holý Antonin: Synthesis of Acyclic Nucleoside Phosphonates. CP Nucleic Acid Chemistry 2005, 22. <https://doi.org/10.1002/0471142700.nc1402s22>
  • Clercq Erik De, Holý Antonín: Acyclic nucleoside phosphonates: a key class of antiviral drugs. Nat Rev Drug Discov 2005, 4, 928. <https://doi.org/10.1038/nrd1877>
  • Pomeisl Karel, Pohl Radek, Holý Antonín, Votruba Ivan: Simple Transformation of Thymine 1-[3-Hydroxy-2-(phosphonomethoxy)propyl] Derivatives to Their 1-[3-Fluoro-2-(phosphonomethoxy)propyl] Counterparts. Collect. Czech. Chem. Commun. 2005, 70, 1465. <https://doi.org/10.1135/cccc20051465>
  • Zídek Zdeněk, Kmoníčková Eva, Holý Antonín: CYTOTOXICITY OF PIVOXIL ESTERS OF ANTIVIRAL ACYCLIC NUCLEOSIDE PHOSPHONATES: ADEFOVIR DIPIVOXIL VERSUS ADEFOVIR. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub 2005, 149, 315. <https://doi.org/10.5507/bp.2005.049>
  • Kmoníčková Eva, Kutinová Canová Nikolina, Farghali Hassan, Holý Antonín, Zídek Zdeněk: Modulator of intracellular Ca2+, Thapsigargin, interferes with in vitro secretion of cytokines and nitric oxide. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub 2005, 149, 321. <https://doi.org/10.5507/bp.2005.050>
  • Zídek Zdenĕk, Kmoníčková Eva, Holý Antonín: Involvement of adenosine A1 receptors in upregulation of nitric oxide by acyclic nucleotide analogues. EUROP J PHARMACOL 2004, 501, 79. <https://doi.org/10.1016/j.ejphar.2004.08.031>
  • Krečmerová Marcela, Masojídková Milena, Holý Antonín: Synthesis of N9- and N7-[2-Hydroxy-3-(phosphonomethoxy)propyl] Derivatives of N6-Substituted Adenines, 2,6-Diaminopurines and Related Compounds. Collect. Czech. Chem. Commun. 2004, 69, 1889. <https://doi.org/10.1135/cccc20041889>
  • Zı́dek Zdeňek, Potměšil Petr, Kmonı́èková Eva, Holý Antonı́n: Immunobiological activity of N-[2-(phosphonomethoxy)alkyl] derivatives of N6-substituted adenines, and 2,6-diaminopurines. EUROP J PHARMACOL 2003, 475, 149. <https://doi.org/10.1016/S0014-2999(03)02110-1>
  • Keith Kathy A., Hitchcock Michael J. M., Lee William A., Holý Antonin, Kern Earl R.: Evaluation of Nucleoside Phosphonates and Their Analogs and Prodrugs for Inhibition of Orthopoxvirus Replication. Antimicrob Agents Chemother 2003, 47, 2193. <https://doi.org/10.1128/AAC.47.7.2193-2198.2003>
  • Holy Antonin, Votruba Ivan, Tloustova Eva, Masojidkova Milena: ChemInform Abstract: Synthesis and Cytostatic Activity of N‐[2‐(Phosphonomethoxy)alkyl] Derivatives of N6‐Substituted Adenines, 2,6‐Diaminopurines and Related Compounds. ChemInform 2002, 33. <https://doi.org/10.1002/chin.200219220>