Synthesis and Anti-HIV Activity of Novel 4′-Trifluoromethylated 5′-Deoxycarbocyclic Nucleoside Phosphonic Acids

REFERENCES

• Maag, H.; Rydzewski, R.M.; McRoberts, M.J.; Crawford-Ruth, D.; Verheyden, J.P.; Prisbe, E.J. Synthesis and anti-HIV activity of 4′-azido- and 4′-methoxynucleosides. J. Med. Chem. 1992, 35, 1440–1451.
   PubMed Web of Science ®Google Scholar
• Sugimoto, I.; Shuto, S.; Mori, S.; Matsuda, A. Synthesis of 4′(α)-branched thymidines as a new type of antiviral agent. Bioorg. Med. Chem. Lett. 1999, 9, 385–388.
   PubMed Web of Science ®Google Scholar
• Boojamra, C.G.; Parrish, J.P.; Sperandio, D.; Gao, Y.; Petrakovsky, O.V.; Lee, S.K.; Markevich, D.Y.; Vela, J.E.; Laflamme, G.; Chen, J.M.; Ray, A.S.; Barron, A.C.; Sparacino, M.L.; Desai, M.C.; Kim, C.U.; Cihlar, T.; Mackman, R.L. Design, synthesis, and anti-HIV activity of 4′-modified carbocyclic nucleoside phosphonate reverse transcriptase inhibitors. Bioorg. Med. Chem. 2009, 17, 1739–1746.
   PubMed Web of Science ®Google Scholar
• Stoeckler, J.D.; Cambor, C.E.;Jr. Parks, R.E. Human erythrocytic purine nucleoside phosphorylase: reaction with sugar-modified nucleoside substrates. Biochemistry 1980, 19, 102–107.
   PubMed Web of Science ®Google Scholar
• Lee, K.; Choi, Y.; Gullen, E.; Schlueter-Wirtz, S.; Schinazi, R.F.; Cheng, Y.C.; Chu, C.K. Synthesis and anti-HIV and anti-HBV activities of 2′-fluoro-2′, 3′-unsaturated L-nucleosides. J. Med. Chem. 1999, 42, 1320–1328.
   PubMed Web of Science ®Google Scholar
• Lee, K.; Choi, Y.; Hong, J.H.; Schinazi, R.F.; Chu, C.K. New classes of fluorinated L-nucleosides; synthesis and antiviral activity. Nucleos. Nucleot. 1999, 18, 537–540.
   PubMedGoogle Scholar
• Xiang, Y.; Kotra, L.P.; Chu, C.K.; Schinazi, R.F. Synthesis and anti-HIV activities of 2′-deoxy-2′,2″-difluoro-β-L-ribofuranosyl-pyrimidine and -purine nucleosides. Bioorg. Med. Chem. Lett. 1995, 5, 743–748.
   Web of Science ®Google Scholar
• Fernandez, R.; Matheu, M.I.; Echarri, R.; Castillon, S. Synthesis of 2-deoxy-3,5-di-O-benzoyl-2,2-difluoro-D-ribose from D-glucose and D-mannose. A formal synthesis of gemcitabine. Tetrahedron 1998, 54, 3523–3532.
   Web of Science ®Google Scholar
• Roy, A.; Schneller, S.W. Enantiospecific synthesis of 5′,5′,5′-trifluoro-5′-deoxyneplanocin A. Tetrahedron Lett. 2005, 46, 8913–8915.
   Web of Science ®Google Scholar
• Zhang, X.; Qing, F.-L. Synthesis of novel L-2′,3′-dideoxy-2′-trifluoromethyl-4′- thiocytidines from α-trifluoromethyl-α,β-unsaturated ester. J. Org. Chem. 2002, 67, 1016–1019.
   PubMed Web of Science ®Google Scholar
• Kozak, J.; Johnson, C.R. Synthesis of 4′-trifluoromethyl nucleoside analogs. Nucleos. Nucleot. 1998, 17, 2221–2239.
   Web of Science ®Google Scholar
• Holy, A. Phosphonomethoxyalkyl analogs of nucleotides. Curr. Pharm. Des. 2003, 9, 2567–2592
   PubMed Web of Science ®Google Scholar
• De Clercq, E.; Holy, A. Phosphonomethoxyalkyl analogs of nucleotides. Nat. Rev. Drug Disc. 2005, 4, 928–940.
   PubMed Web of Science ®Google Scholar
• Jones, G.H.; Moffat, J.G. The synthesis of 6′-deoxyhomonucleoside-6′-phosphonic acids. J. Am. Chem. Soc. 1968, 90, 5336–5338.
   PubMed Web of Science ®Google Scholar
• De Clercq, E. The clinical potential of the acyclic (and cyclic) nucleoside phosphonates: the magic of the phosphonate bond. Biochem. Pharmacol. 2011, 82, 99–109.
   PubMed Web of Science ®Google Scholar
• Balzarini, J.; Hao, Z.; Herdewijn, P.; Johns, D.G.; De Clercq, E. Intracellular metabolism and mechanism of anti-retrovirus action of 9-(2-phosphonylmethoxyethyl)adenine, a potent anti-human immunodeficiency virus compound. Proc. Natl. Acad. Sci U S A. 1991, 88, 1499–1503.
   PubMed Web of Science ®Google Scholar
• Magee, W.C. K.; Aldern, A.; Hostetler, K.Y.; Evans, D.H. Cidofovir and (S)-9-[3-hydroxy-(2-phosphonomethoxy)propyl]adenine are highly effective inhibitors of vaccinia virus DNA polymerase when incorporated into the template strand. Antimicrob. Agents Chemother. 2008, ;52, 586–597.
   PubMed Web of Science ®Google Scholar
• Wu, T.; Froeyen, M.; Kempeneers, V.; Pannecouque, C.; Wang, J.; Busson, R.; De Clercq, E.; Herdewijn, P. Deoxythreosyl phosphonate nucleosides as selective anti-HIV agents. J. Am. Chem. Soc. 2005, 127, 5056–5065.
   PubMed Web of Science ®Google Scholar
• Koh. Y.H.; Shim, J.H.; Wu, J.Z.; Zhong, W.; Hong, Z.; Girardet, J.L. Design, synthesis, and antiviral activity of adenosine 5′-phosphonate analogues as chain terminators against hepatitis C virus. J. Med. Chem. 2005, 48, 2867–2875.
   PubMed Web of Science ®Google Scholar
• Kim, C.U.; Luh, B.Y.; Misco, P.F.; Bronson, J.J.; Hitchcock, M.J.; Ghazzouli, I.; Martin, J.C. Acyclic purine phosphonate analogues as antiviral agents. Synthesis and structure-activity relationships. J. Med. Chem. 1990, 33, 1207–1213.
   PubMed Web of Science ®Google Scholar
• Kim, S.; Kim, E.; Lee, W.; Hong, J.H. Synthesis and antiviral evaluation of novel 4′-trifluoromethylated 5′-deoxythreosyl phosphonic acid nucleosides. Nucleosides Nucleotides & Nucleic Acids 2014, 33, 747–766.
   PubMed Web of Science ®Google Scholar
• Marshall, J.A.Gung, W.Y. On the 1,3-isomerization of nonracemic α-(alkoxy) allylstannanes. Tetrahedron Lett. 1989, 30, 7349–7352.
   Web of Science ®Google Scholar
• Mancuso, A.J.; Huang, S.L.; Swern, D. Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide “activated” by oxalyl chloride. J. Org. Chem. 1978, 43, 2480–2482.
   Web of Science ®Google Scholar
• Maryanoff, B.E.; Reitz, A.B. The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects. Chem. Rev. 1989, 89, 863–927.
   Web of Science ®Google Scholar
• Kozikowski, A.P.; Wu, J.P. Protection of alcohol as their (p-methoxybenzyloxy)methyl ethers. Tetrahedron Lett. 1987, 28, 5125–5128.
   Web of Science ®Google Scholar
• Diaz, Y.; Bravo, F.; Castillon, S. Synthesis of purine and pyrimidine isodideoxynucleosides from (S)-glycydol using iodoetherification as key step. synthesis of (S,S)-iso-ddA. J. Org. Chem. 1999, 64, 6508–6511.
   Web of Science ®Google Scholar
• Montagu, A.; Pradere, U.; Roy, V.; Nolan, S.P.; Agrofoglio, L.A. Expeditious convergent procedure for the preparation of bis(POC) prodrug of new (E)-4-phosphono-but-2-en-yl nucleosides. Tetrahedron 2011, 67, 5317–5328.
   Web of Science ®Google Scholar
• Huang, Q.; Herdewijn, P. Synthesis of (E)-3′-phosphonoalkenyl modified nucleoside phosphonates via a highly stereoselective olefin cross-metathesis reaction. J. Org. Chem. 2011, 76, 3742–3753.
   PubMed Web of Science ®Google Scholar
• Scholl, M.; Ding, S.; Lee, C.W.; Grubbs, R.H. Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimethyl-4,5-dihydroimidazole-2-ylidene ligands. Org. Lett. 1999, 1, 953–956.
   PubMed Web of Science ®Google Scholar
• Hocková, D.; Holý, A.; Masojídková, M.; Keough, D.T.; De Jersey, J.; Guddat, L.W. Synthesis of branched 9-[2-(2-phosphonoethoxy)ethyl]purines as a new class of acyclic nucleoside phosphonates which inhibit Plasmodium falciparum hypoxanthine-guanine-xanthine phosphoribosyltransferase. Bioorg. Med. Chem. 2009, 17, 6218–6232.
   PubMed Web of Science ®Google Scholar
• Robins, M.J.; Uznanski, B. Non-aqueous diazotization with t-butyl nitrite. Introduction of fluorine, chlorine, and bromine at C-2 of purine nucleoside. Can. J. Chem. 1981, 59, 2608–2611.
   Web of Science ®Google Scholar
• Montgomery, J.; Hewson,K. Nucleosides of 2-fluoroadenine. J. Med. Chem. 1969, 12, 498–504.
   PubMed Web of Science ®Google Scholar
• Tong, G.L.; Ryan, K.J.; Lee, W.W.; Acton, E.M.; Goodman, L. Nucleosides of thioguanine and other 2-amino-6-substituted purines from 2-acetamido-5-chloropurine. J. Org. Chem. 1967, 32, 859–862.
   PubMed Web of Science ®Google Scholar
• Koyanagi. Y.; Harada, S.; Takahashi, M.; Uchino, F.; Yamamoto, N. Selective cytotoxicity of AIDS virus towards HTLV-1 transformed cell lines. Int. J. Cancer 1985, 36, 445–451.
   PubMed Web of Science ®Google Scholar
• Pauwels, R.; Balzarini, J.; Baba, M.; Snoeck, R.; Schols, D.; Herdewijn, P.; Desmyter, J.; De Clercq, E. Rapid and automated tetrazolium-based colorimetric assay for the detection of anti-HIV compounds. J. Virol. Methods 1988, 20, 309–321.
   PubMed Web of Science ®Google Scholar