Design and Synthesis of 2′-Deoxy-2′-[(1,2,3)Triazol-1-Yl]Uridines Using Click Chemistry Approach

REFERENCES

• Kukhanova, M.; Krayevsky, A.; Prusoff, W.; Cheng, Y. Design of anti-HIV compounds from nucleoside to nucleoside 5-triphosphate analogs. Problems and perspectives. Curr. Pharm. Des. 2000, 6, 585–598.
   PubMed Web of Science ®Google Scholar
• Galmarini, C.; Mackey, J.; Dumontet, C. Nucleoside analogues and nucleobases in cancer treatment. Lancet Oncol. 2002, 3, 415–424.
   PubMed Web of Science ®Google Scholar
• Iyer, R.; Padmanabhan, S.; Zhang, G.; Morrey, J.; Korba, B. Nucleotide analogs as novel anti-hepatitis B virus agents. Curr. Opin. Pharmacol. 2005, 5, 520–528.
   PubMed Web of Science ®Google Scholar
• Tang, Y.B.; Peng, Z.G.; Liu, Z.Y.; Li, Y.P.; Jiang, J.D.; Li, Z.R. Some new acyclic nucleotide analogues as antiviral prodrugs: Synthesis and bioactivities in vitro. Bioorg. Med. Chem. Lett. 2007, 17, 6350–6353.
   PubMed Web of Science ®Google Scholar
• Cihlar, T.; Ray, A.S. Nucleoside and nucleotide HIV reverse transcriptase inhibitors: 25 years after zidovudine. Antiviral Res. 2010, 85, 39–58.
   PubMed Web of Science ®Google Scholar
• (a) Wan, J.; Xia, Y.; Liu, Y.; Wang, M.; Rocchi, P.; Yao, J.; Qu, F.; Neyts, J.; Iovanna, J.L.; Peng, L. Discovery of novel arylethynyltriazole ribonucleosides with selective and effective antiviral and anti-proliferative activity. J. Med. Chem., 2009, 52, 1144–1155.
   PubMed Web of Science ®Google Scholar
• Montague, A.; Roy, V.; Balzarini, J.; Snoeck, R.; Andrei, G.; Agrofoglio, L.A. Synthesis of new C5-(1-substituted-1,2,3-triaole-4 or 5-yl)-2-deoxyuridines and their antiviral evaluation. Eur. J. Med. Chem. 2011, 46, 778–786.
   PubMed Web of Science ®Google Scholar
• Ferreira, M.D.L.G.; Pinheiro, L.C.S.; Filho, O.A.S.; Peçanha, M.D.S.; Sacramento, C.Q.; Machado, V.; Ferreira, V.F.; Souza, T.M.L.; Boechat, N. Design, synthesis, and antiviral activity of new 1H-1,2,3-triazole nucleoside ribavirin analogs. Med. Chem. Res. 2014, 23, 1501–1511.
   Web of Science ®Google Scholar
• Kirschberg, T.A.; Balakrishnan, M.; Huang, W.; Hluhanich, R.; Kutty, N.; Liclican, A.C.; McColl, D.J.; Squires, N.H.; Lansdon, E.B. Triazole derivatives as non‐nucleoside inhibitors of HIV‐1 reverse transcriptase – Structure–activity relationships and crystallographic analysis. Bioorg. Med. Chem. Lett. 2008, 18, 1131–1134.
   PubMed Web of Science ®Google Scholar
• Khalil, N.S.A.M. Efficient synthesis, structure and antimicrobial activity of some novel N‐ and S‐β‐D‐glucosides of 5‐pyridin‐3‐yl‐1,2,4‐triazoles. Carbohydr. Res. 2006, 341, 2187–2199.
   PubMed Web of Science ®Google Scholar
• Kumar, J.M.; Idris, M.M.; Srinivas, G.; Kumar, P.V.; Meghah, V.; Kavitha, M.; Reddy, C.R.; Mainkar, P.S.; Pal, B.; Chandrasekar, S.; Nagesh, N. Phenyl 1,2,3-triazole-thymidine ligands stabilize G-quadruplex DNA, inhibit DNA synthesis and potentially reduce tumor cell proliferation over 3′-azido deoxythymidine. PLOS One 2013, 8, e70798.
   PubMed Web of Science ®Google Scholar
• Yu, J.L.; Wu, Q.P.; Zhang, Q.S.; Liu, Y.H.; Li, Y.Z.; Zhou, Z.M. Synthesis and antitumor activity of novel 2′,3′‐dideoxy‐2′,3′‐diethane thionucleosides bearing 1,2,3‐triazole residues. Bioorg. Med. Chem. Lett. 2010, 20, 240–243.
   PubMed Web of Science ®Google Scholar
• (a) Amblard, F.; Cho, J.H.; Shinazi, R.F. Cu(I)-catalyzed Huisgen Azide-Alkyne 1,3-dipolar cycloaddition reaction in nucleoside, nucleotide, and oligonucleotide chemistry. Chem. Rev. 2009, 109, 4207–4220.
   PubMed Web of Science ®Google Scholar
• Pradere, U.; Roy, V.; McBrayer, R.T.; Schinazi, R.F.; Agrofoglio, L.A. Preparation of ribavirin analogues by copper- and ruthenium-catalyzed azide-alkyne 1,3-dipolar cycloaddition. Tetrahedron 2008, 64, 9044–9051.
   PubMed Web of Science ®Google Scholar
• Elakri, K.; Bougrin, K.; Balzarini, J.; Faraj, A.; Benhida, R. Efficient synthesis and in vitro cytostatic activity of 4-substituted triazolyl-nucleosides. Bioorg. Med. Chem. Lett. 2007, 17, 6656–6659.
   PubMed Web of Science ®Google Scholar
• Seela, F.; Pujari, S.S.; Schafer, A.H. Hydrogelation and spontaneous fiber formation of 8-aza-7-deazaadenine nucleoside “click” conjugates. Tetrahedron 2011, 67, 7418–7425.
   Web of Science ®Google Scholar
• (a) Alvarez, R.; Velazquez, S.; San-Felix, A.; Aquaro, S.; De Clercq, E.; Perno, C-F.; Karlsson, A.; Balzarini, J.; Camarasa, M.J. 1,2,3-Triazole-[2,5-Bis-O-(tert-butyldimethylsilyl)-.beta.-D-ribofuranosyl]-3′-spiro-5′′-(4′′-amino-1′′,2′′-oxathiole 2′′,2′′-dioxide) (TSAO) analogs: Synthesis and anti-HIV-1 activity. J. Med. Chem. 1994, 37, 4185–4194.
   PubMed Web of Science ®Google Scholar
• Chaudhary, P.M.; Chavan, S.R.; Shirazi, F.; Razdan, M.; Nimkar, P.; Maybhate, S.P.; Likhite, A.P.; Gonnade, R.; Hazara, B.G.; Deshpande, M.V.; Deshpande, S.R. Exploration of click reaction for the synthesis of modified nucleosides as chitin synthase inhibitors. Bioorg. Med. Chem. 2009, 17, 2433–2440.
   PubMed Web of Science ®Google Scholar
• Zhou, L.; Amer, A.; Korn, M.; Burda, R.; Balzarini, J.; De Clercq, E.; Kern, E.R.; Torrence, P.F. Synthesis and antiviral activities of 1,2,3-triazole functionalized thymidines: 1,3-dipolar cycloaddition for efficient regioselective diversity generation. Antivi. Chem. Chemother. 2005, 16, 375–383.
   PubMedGoogle Scholar
• Mahony, G.O.; Svensson, S.; Sundgren, A.; Grotli, M. Synthesis of 2′-([1,2,3]triazol-1-yl)-2′-deoxyadenosines. Nucleos. Nucleot. Nucl. 2008, 27, 449–459.
   PubMed Web of Science ®Google Scholar
• Hampton, A.; Nichol, A.W. Nucleosides V purine ribonucleoside 2′,3′-cyclic carbonates. Preparation and use for the synthesis of 5′-monosubstituted nucleosides. Biochemistry 1966, 5, 2076–2082.
   PubMed Web of Science ®Google Scholar
• Kirschenheuter, G.P.; Zhai, Y.; Pieken, W.A. An improved synthesis of 2′-azido-2′-deoxyuridine. Tetrahedron Lett. 1994, 35, 8517–8520.
   Web of Science ®Google Scholar