Synthesis and biological assay of new 2’-deoxyuridine dimers containing a 1,2,3-triazole linker. Part I

References

• Block, J.H.; Beale, J. M. Organic Medicinal and Pharmaceutical Chemistry; Lippincott Williams & Wilkins, London, Eleventh edition, 2004.
   Google Scholar
• Dheer, D.; Singh, V.; Shankar, R. Medicinal Attributes of 1,2,3-Triazoles: Current Developments. Bioorg. Chem. 2017, 71, 30–54.
   PubMed Web of Science ®Google Scholar
• Pałasz, A.; Cież, D.; In Serach of Uracil Derivatives as Bioactive Agents. Uracils and Fused Uracils: Synthesis, Biological Activity and Applications. Eur. J. Med. Chem. 2015, 97, 582–611.
   PubMed Web of Science ®Google Scholar
• Pastuch-Gawolek, G.; Plesniak, M.; Komor, R.; Byczek-Wyrostek, A.;Erfurt, K.; Szeja, W. Synthesis and preliminary biological assai of uridine glycoconjugate derivatives containing amide and/or 1,2,3-triazole linkers, Bioorg. Chem. 2017, 72, 80–88.
   PubMed Web of Science ®Google Scholar
• Goz, B.; Walker, K.P. An Immunological and Biochemical Analysis of Alkaline Phosphatase in HeLa Cells Exposed to 5-iodo-2’-Deoxyuridine. Biochem. Pharmacol. 1978, 27, 431–436.
   PubMed Web of Science ®Google Scholar
• De Clercq, E. Antiviral Drugs in Current Clinical Use. J. Clin. Virol. 2004, 30, 115–133.
   PubMed Web of Science ®Google Scholar
• Grem, J.L. 5-Fluorouracil: Forty-Plus and Still Ticking. A Review of its Preclinical and Clinical Development. Invest. New Drugs. 2000, 18, 299–313.
   PubMed Web of Science ®Google Scholar
• Longley, D.B.; Harkin, D.P.; Johnston, P.G. 5-Fluorouracil: Mechanisms of Action and Clinical Strategies. Nat. Rev. Cancer. 2003, 3, 330–338.
   PubMed Web of Science ®Google Scholar
• Hamuy, R.; Berman, B. Topical antiviral agents for herpes simplex virus infections, Drugs Today 1998, 34, 1013–1025.
   PubMed Web of Science ®Google Scholar
• Olofsson, S.; Sjöblom, I.; Hellstrand, K.; Shugar, D.; Clairmont, C.; Hirschberg, C. 5-Propyl-2’-Deoxyuridine Induced Interference with Glycosylation in Herpes Simplex Virus Infected Cells. Nature of PdU-Induced Modifications of N-Linked Glycans. Arch. Virol. 1993, 128, 241–256.
   PubMed Web of Science ®Google Scholar
• De Clercq, E. (E)-(2-Bromovinyl)-2’-Deoxyuridine (BVDU). Med. Res. Rev. 2005, 25, 1–20.
   PubMed Web of Science ®Google Scholar
• Wójtowicz-Rajchel, H. Synthesis and Applications of Fluorinated Nucleoside Analogues. J. Fluor. Chem. 2012, 143, 11–48.
   Web of Science ®Google Scholar
• Ashwell, M.; Jones, A. S.; Kumar, A.; Sayers, J. R.; Walker, R. T.; Sakuma, T. The Synthesis and Antiviral properties of (E)-5-(2-bromovinyl)-2’-deoxyuridine-related compounds, Tetrahedron 1987, 43, 4601–4608.
   Web of Science ®Google Scholar
• Degrève, B.; De Clercq, E.; Balzarini, J. Bystander Effect of Purine Nucleoside Analogues in HSV-1 tk Suicide Gene Therapy is Superior to That of Pyrimidine Nucleoside Analogues. Gene Ther. 1999, 6, 162–170.
   PubMed Web of Science ®Google Scholar
• Cameron, J. M. New Antiherpes Drugs in Development. Rev. Med. Virol. 1993, 3, 225–236.
   Web of Science ®Google Scholar
• Degrève, B.; de Clercq, E.; Karlsson, A.; Balzarini, J. Efficacy of Antiherpetic Drugs in Combined Gene/Chemotheraphy of Cancer is not Affected by a Specific Nuclear or Cytoplasmic Compartmentation of Herpes Thymidine Kinases. Gene Ther. Mol. Biol. 1999, 3, 123–131.
   Google Scholar
• De Clercq, E.; Descamps, J.; De Somer, P.; Barr, P. J.; Jones, A. S.; Walker, R. T. (E)-5-(2-Bromovinyl)-2’-Deoxyuridine: A Potent and Selective Anti-Herpes Agent. Proc. Natl. Acad. Sci. USA. 1979, 76, 2947–2951.
   PubMed Web of Science ®Google Scholar
• Meneni, S.; Ott, I.; Sergeant, C. D.; Sniady, A.; Gust, R.; Dembinski, R. 5-Alkynyl-2’-Deoxyuridines: Chromatography-Free Synthesis and Cytotoxicity Evaluation Against Human Breast Cancer Cells. Bioorg. Med. Chem. 2007, 15, 3082–3088.
   PubMed Web of Science ®Google Scholar
• Raić–Malić, S.; Meščić, A. Recent Trends in 1,2,3-Triazolo-Nucleosides as Promising Anti-Infective and Anticancer Agents. Curr. Med. Chem. 2015, 22, 1462–1499.
   PubMed Web of Science ®Google Scholar
• Kolb, H.C.; Finn, M. G.; Sharpless, K. B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angew. Chem., Int. Ed. 2001, 40, 2004–2021.
   PubMed Web of Science ®Google Scholar
• Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, B. K. A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective Ligation of Azides and Terminal Alkynes, Angew Chem., Int. Ed. 2002, 41, 2596–2599.
   PubMed Web of Science ®Google Scholar
• Tornøe, C.W.; Christensen, C.; Meldal, M. Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides. J. Org. Chem. 2002, 67, 3057–3064.
   PubMed Web of Science ®Google Scholar
• Kore, A.R.; Charles, I. Click chemistry Based Functionalizations of Nucleoside, Nucleotide and Nucleic Acids, Curr. Org. Chem. 2013, 17, 2164–2191.
   Web of Science ®Google Scholar
• Lucas, R.; Neto, V.; Bouazza, A. H.; Zerrouki, R.; Granet, R.; Krausz, P; Champavier, Y. Microwave-assisted synthesis of a triazole-linked 3′?5′ dithymidine using click chemistry. Tetrahedron Lett. 2008, 49, 1004–1007.
   Web of Science ®Google Scholar
• Nyilas, A.; Glemarec, C.; Chattopadhyaya, J.; Synthesis of [3t'(O)→-5t'(c)]-Oxyacetamido Linked Nucleosides. Tetrahedron. 1990, 46, 2149–2164.
   Web of Science ®Google Scholar
• Baraniak, D.; Baranowski, D.; Ruszkowski, P.; Boryski, J. 3'-O- and 5'-O-Propargyl Derivatives of 5-Fluoro-2'-Deoxyuridine: Synthesis, Cytotoxic Evaluation and Conformational Analysis. 3'-O- and 5'-O-Propargyl Derivatives of 5-Fluoro-2'-Deoxyuridine: Synthesis, Cytotoxic Evaluation and Conformational Analysis. Nucleosides Nucleotides and Nucleic Acids 2016, 35, 178–194.
   PubMed Web of Science ®Google Scholar
• Azizi, S.A.; Miyamoto, C. Principles of Treatment of Malignant Gliomas in Adults: An Overview. J. Neurovirol. 1998,4, 204–216.
   PubMed Web of Science ®Google Scholar
• (a) Yamanaka, R.; Saya, H. Molecularly Targeted Therapies for Glioma. Ann. Neurol. 2009, 66, 717–729;
   PubMed Web of Science ®Google Scholar
  (b) Giese, A.; Bjerkvig, R.; Berens, M.E.; Westphal, M. Cost of Migration: Invasion of Malignant Gliomas and Implications for Treatment. J. Clin. Oncol. 2003, 21, 1624–1636.
   PubMed Web of Science ®Google Scholar
• (a) Framski, G.; Wawrzyniak, D.; Jahnz-Wechmann, Z.; Szymańska-Michalak, A.; Kraszewski, A.; Barciszewski, J.; Boryski, J.; Stawinski, J. Searching for Anti-Glioma Activity. Ribonucleoside Analogues with Modifications in Nucleobase and Sugar Moieties, Acta Biochim. Pol. 2016, 63, 765–771;
   PubMed Web of Science ®Google Scholar
  (b) Szymańska-Michalak, A.; Wawrzyniak, D.; Framski, G.; Kujda, M.; Zgoła, P.; Stawinski, J.; Barciszewski, J.; Boryski, J.; Kraszewski, A. New 3'-O-Aromatic Acyl-5-Fluoro-2'-Deoxyuridine Derivatives as Potential Anticancer Agents. Eur. J. Med. Chem. 2016, 10, 41–52.
   Google Scholar
• Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. New Colorimetric Cytotoxicity Assay for Anticancer-Drug Screening. J. Natl. Cancer Inst. 1990, 82, 1107–1112.
   PubMed Web of Science ®Google Scholar
• Pedretti, A.; Villa, L.; Vistoli, G. VEGA: a versatile program to convert, handle and visualize molecular structure on Windows-based PCs. J. Mol. Graph Model. 2002, 21, 47–49.
   PubMed Web of Science ®Google Scholar
• Tetko, I.V.; Gasteiger, J.; Todeschini, R.; Mauri, A.; Livingstone, D.; Ertl, P.; Palyulin, V.A.; Radchenko, E.V.; Zefirov, N.S.; Makarenko, A.S.; et al. J. Comput. Aided Mol. Des. 2005, 19, 453–463.
   PubMed Web of Science ®Google Scholar
• Lipinski, C.A.; Lombardo, F.; Dominy, B.W.; Feeney, P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings, Adv. Drug Deliv. Rev. 2001, 46, 3–26.
   PubMed Web of Science ®Google Scholar
• Yazdanian, M. Correlating Partitioning and Caco-2 Cell Permeability Of Structurally Diverse Small Molecular Weight Compounds. Pharm. Res. 1998, 15, 1490–1494.
   PubMed Web of Science ®Google Scholar
• Clark, D.E. Rapid Calculation of Polar Molecular Surface Area and Its Application to the Prediction of Transport Phenomena. 1. Prediction of Intestinal Absorption. J. Pharm. Sci. 1999, 88, 807–814.
   PubMed Web of Science ®Google Scholar
• Kelder, J., Grootenhuis, P. D.; Bayada, D. M.; Delbressine, L. P.; Ploemen, J. P. Polar Molecular Surface as a Dominating Determinant for Oral Absorption and Brain Penetration of Drugs. Pharm Res. 1999, 16, 1514–1519.
   PubMed Web of Science ®Google Scholar
• Patel, P. L.; Rana, N. K.; Patel, M. R.; Kozuch, S. D.; Sabatino, D. Nucleic Acid Bioconjugates in Cancer Detection and Theraphy. ChemMedChem 2016, 11, 252–269.
   PubMed Web of Science ®Google Scholar