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Collect. Czech. Chem. Commun. 2006, 71, 595-624
https://doi.org/10.1135/cccc20060595

Syntheses of Base and Side-Chain Modified Pyrimidine 1-[2-(Phosphonomethoxy)propyl] Derivatives as Potent Inhibitors of Thymidine Phosphorylase (PD-ECGF) from SD-Lymphoma

Karel Pomeisl*, Ivan Votruba, Antonín Holý and Radek Pohl

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

Crossref Cited-by Linking

  • Feng Qianqian, Yang Wei, Peng Zhiyun, Wang Guangcheng: Recent advances in the synthetic thymidine phosphorylase inhibitors for cancer therapy. European Journal of Pharmacology 2022, 934, 175319. <https://doi.org/10.1016/j.ejphar.2022.175319>
  • Dorababu Atukuri: Evolution of uracil based thymidine phosphorylase inhibitors, SAR and electronic correlation: revisit. Drug Development Research 2019, 80, 893. <https://doi.org/10.1002/ddr.21592>
  • Pomeisl Karel, Krečmerová Marcela, Pohl Radek, Snoeck Robert, Andrei Graciela: Synthesis of fluorinated acyclic nucleoside phosphonates with 5-azacytosine base moiety. Tetrahedron 2019, 75, 130529. <https://doi.org/10.1016/j.tet.2019.130529>
  • Pomeisl Karel, Beier Petr, Pohl Radek, Krečmerová Marcela: Novel and Efficient Synthesis of gem‐Difluorinated Derivatives of Acyclic Nucleoside Phosphonates (ANPs). ChemistrySelect 2016, 1, 2102. <https://doi.org/10.1002/slct.201600445>
  • Parchina Anastasia, Froeyen Matheus, Margamuljana Lia, Rozenski Jef, De Jonghe Steven, Briers Yves, Lavigne Rob, Herdewijn Piet, Lescrinier Eveline: Discovery of an Acyclic Nucleoside Phosphonate that Inhibits Mycobacterium tuberculosis ThyX Based on the Binding Mode of a 5‐Alkynyl Substrate Analogue. ChemMedChem 2013, 8, 1373. <https://doi.org/10.1002/cmdc.201300146>
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  • Pomeisl Karel, Horská Květoslava, Pohl Radek, Blažek Jiří, Krečmerová Marcela: Syntheses of 1-[2-(Phosphonomethoxy)Alkyl]Thymine Monophosphates and an Evaluation of their Inhibitory Activity Toward Human Thymidine Phosphorylase. NUCLEOT NUCL 2012, 31, 159. <https://doi.org/10.1080/15257770.2011.648361>
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  • Houghton Stephen R., Melton Jack, Fortunak Joseph, Brown Ripin David H., Boddy Christopher N.: Rapid, mild method for phosphonate diester hydrolysis: development of a one-pot synthesis of tenofovir disoproxil fumarate from tenofovir diethyl ester. Tetrahedron 2010, 66, 8137. <https://doi.org/10.1016/j.tet.2010.08.037>
  • Janeba Zlatko, Holý Antonín, Pohl Radek, Snoeck Robert, Andrei Graciela, De Clercq Erik, Balzarini Jan: Synthesis and biological evaluation of acyclic nucleotide analogues with a furo[2,3-d]pyrimidin-2(3H)-one base. Can. J. Chem. 2010, 88, 628. <https://doi.org/10.1139/V10-054>
  • Birck Matthew R., Clinch Keith, Gainsford Graeme J., Schramm Vern L., Tyler Peter C.: Syntheses of 5‐Chlorouracils/Thymines with 1‐[Phosphono(Methyl/Difluoromethyl)]‐1,2‐Unsaturated‐Moiety‐Substituted Methyl Groups at N(1) and Human Thymidine Phosphorylase Inhibitory Activity. Helvetica Chimica Acta 2009, 92, 823. <https://doi.org/10.1002/hlca.200900003>
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  • Pomeisl Karel, Holý Antonín, Pohl Radek, Horská Květoslava: Use of Pd-catalyzed Suzuki–Miyaura coupling reaction in the rapid synthesis of 5-aryl-6-(phosphonomethoxy)uracils and evaluation of their inhibitory effect towards human thymidine phosphorylase. Tetrahedron 2009, 65, 8486. <https://doi.org/10.1016/j.tet.2009.08.039>
  • Pomeisl Karel, Holý Antonín, Votruba Ivan, Pohl Radek: Syntheses of N3-substituted thymine acyclic nucleoside phosphonates and a comparison of their inhibitory effect towards thymidine phosphorylase. Bioorganic & Medicinal Chemistry Letters 2008, 18, 1364. <https://doi.org/10.1016/j.bmcl.2008.01.006>
  • Pomeisl Karel, Holý Antonín, Pohl Radek: Pd-catalyzed Suzuki–Miyaura coupling reactions in the synthesis of 5-aryl-1-[2-(phosphonomethoxy)ethyl]uracils as potential multisubstrate inhibitors of thymidine phosphorylase. Tetrahedron Letters 2007, 48, 3065. <https://doi.org/10.1016/j.tetlet.2007.02.107>
  • Pomeisl Karel, Votruba Ivan, Holý Antonín, Pohl Radek: Syntheses of Pyrimidine Acyclic Nucleoside Phosphonates as Potent Inhibitors of Thymidine Phosphorylase (PD-ECGF) from SD-Lymphoma. Nucleosides, Nucleotides & Nucleic Acids 2007, 26, 1025. <https://doi.org/10.1080/15257770701508679>
  • Pomeisl Karel, Votruba Ivan, Holy Antonin, Pohl Radek: Synthesis of Base and Side‐Chain Modified Pyrimidine 1‐[2‐(Phosphonomethoxy)propyl] Derivatives as Potent Inhibitors of Thymidine Phosphorylase (PD‐ECGF) from SD‐Lymphoma. ChemInform 2006, 37. <https://doi.org/10.1002/chin.200637174>