Synthesis of Novel 4′-Trifluoromethyl-5′-Norcarbocyclic C-Nucleoside Phosphonic Acids as Potent Anti-Leukemic Agents

REFERENCES

• 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
• Ray, A.S.; Vela, J.E.; Boojamra, C.G.; Zhang, L.; Hui, H.; Callebaut, C.; Stray, K.; Lin, K.Y.; Gao, Y.; Mackman, R.L.; Cihlar, T. Intracellular metabolism of the nucleotide prodrug GS-9131, a potent anti-human immunodeficiency virus agent. Anti-microb. Agents Chemother. 2008, 52, 648–654
   PubMed Web of Science ®Google Scholar
• Boojamra, C.G.; Mackman, R.L.; Markevitch, D.Y.; Prasad, V.; Ray, A.S.; Douglas, J.; Grant, D.; Kim, C.U.; Cihlar, T. Synthesis and anti-HIV activity of GS-9148 (2′-Fd4AP), a novel nucleoside phosphonate HIV reverse transcriptase inhibitor. Bioorg. Med. Chem. Lett. 2008, 18, 1120
   PubMed Web of Science ®Google Scholar
• Cihlar, T.; Ray, A.S.; Boojamra, C.G.; Zhang, L.; Hui, H.; Laflamme, G.; Vela, J.E.; Grant, D.; Chen, J.; Myrick, F.; White, K.L.; Gao, Y.; Lin, K.Y.; Douglas, J.L.; Parkin, N.T.; Carey, A.; Pakdaman, R.; Mackman, R.L. Design and profiling of GS-9148, a novel nucleotide analog active against nucleoside-resistant variants of human immunodeficiency virus type 1, and its orally bioavailable phosphonoamidate prodrug, GS-9131. Antimicrob. Agents Chemother. 2008, 52, 655–665.
   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
• 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, C.U.; Luh, B.Y.; Martin, J.C. Regiospecific and highly stereoselective electrophilic addition to furanoid glycals: synthesis of phosphonate nucleotide analogs with potent activity against HIV. J. Org. Chem. 1991, 56, 2642–2647.
   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 USA. 1991, 88, 1499–1503.
   PubMed Web of Science ®Google Scholar
• Shaban, M.A.E.; Nasr, A.Z. The chemistry of C- nucleosides and their analogs I: C-nucleosides of hetero monocyclic bases. Adv. Heterocycl. Chem. 1997, 68, 223–432
   Web of Science ®Google Scholar
• Shaban, M.A.E. The chemistry of C-nucleosides and their analogs II: C-nucleosides of condensed heterocylic bases. Adv. Heterocycl. Chem. 1997, 70, 163–337
   Web of Science ®Google Scholar
• Liang, C.; Ma, T.; Cooperwood, J.S.; Du, J.; Chu, C.K. Synthesis of L-ribofuranosyl C-nucleosides. Carbohydr. Res. 1997, 303, 33–38
   PubMed Web of Science ®Google Scholar
• Zhou, J.; Yang, M.; Akdag, A.; Wang, H.; Schneller, S.W. Carbocyclic 4′-Epiformycin. Tetrahedron 2008, 64, 433–438.
   PubMed Web of Science ®Google Scholar
• Buchenal, J.H.; Ciovacco, K.; Kalaher, K.; O’Toole, T.; Kiefner, R.; Dowing, M.D.; Chu, C.K.; Watanabe, K.A.; Wempen, I.; Fox, J.J. Antileukemic effects of pseudoisocytidine, a new synthetic pyrimidine C-nucleoside. Cancer Res. 1976, 36, 1520–1523.
   PubMed Web of Science ®Google Scholar
• Fuertes, M.; Garcia-Lopez, M.T.; Garcia-Munoz, G.; Stud, M. Synthesis of C-glycosyl thiazole. J. Org. Chem. 1976, 41, 4074–4077
   Web of Science ®Google Scholar
• Srivastava, P.C.; Pickering, M.V.; Allen, L.B.; Streeter, D.C.; Campbell, M.T.; Witkowski, J.T.; Sidwell, R.W.; Robins, R.K. Synthesis and antiviral activity of certain thiazole C-nucleosides. J. Med. Chem. 1977, 20, 256–262.
   PubMed Web of Science ®Google Scholar
• Srivastava, P.C.; Robins, R.K. Synthesis and antitumor activity of 2-β-D-ribofuranosylselenazole-4-carboxamide and related derivatives. J. Med. Chem. 1983, 26, 445–448.
   PubMed Web of Science ®Google Scholar
• Chu, C.Y.; Zuckerman, L.B.; Sato, S.; Crabtree, G.W.; Bogden, A.E.; Lim, M.I.; Klein, R.S. 9-Deazaadenosine-a new potent antitumor agent. Biochem. Pharmacol. 1984, 33, 1229–1234
   PubMed Web of Science ®Google Scholar
• Zimmerman, T.P.; Deeprose, R.D.; Wolberg, G.; Stopford, C.R.; Duncan, G.S.; Miller, W.H.; Miller, R.L.; Lim, M.I.; Ren, W.Y.; Klein, R.S. Inhibition of lymphocyte function by 9-deazaadenosine. Biochem. Pharmacol. 1983, 32, 1211–1217.
   PubMed Web of Science ®Google Scholar
• Tam, S.Y.-K.; Klein, R.S.; Wempen, I.; Fox, J.J. Synthesis of some new pyrazolo[1,5-a]-1,3,5-triazines and their C-nucleosides. J. Org. Chem. 1979; 44, 4547–4553
   Web of Science ®Google Scholar
• Tam, S.Y.-K.; Hwang, J.S.; De Las Heras, F.G.; Klein, R.S.; Fox, J.J. Synthesis of the 8-(β-D-ribofuranosyl)pyrazolo[1,5-a]-1,3,5-triazine isosteres of adenosine and inosine. J. Heterocycl. Chem. 1976, 13, 1305–1308.
   Web of Science ®Google Scholar
• Fissekis, J.D.; Creegan, B.M. Synthesis of 5-hydroxyalkylpyrimidines from lactones. III. 5-Dihydroxycyclopentyl pyrimidines. J. Org. Chem. 1967, 32, 3595–3603
   Web of Science ®Google Scholar
• Katagiri, N.; Haneda, T.; Kaneko, C. Facile synthesis of the carbocyclic analogue of β-ribofuranosyl-malonate, new synthon for carbocyclic C-nucleoside formation by retrograde aldol C-C bond fission. Chem. Pharm. Bull. 1986, 34, 4875–4878
   Web of Science ®Google Scholar
• Katagiri, N.; Haneda, T.; Hayasaka, E.; Watanabe, N.; Kaneko, C. Di-l-menthyl (acetoxymethylene) malonate, a new chiral dienophile: Enantioselective route to carbocyclic analogs of C-nucleoside. J. Org. Chem. 1988, 53, 226–227
   Web of Science ®Google Scholar
• Lee, C.H.; Kim, J.Y.; Kim, W.J.; Kim, Y.H. Facile synthesis of tetrahydro-2-furylated pyrimidines and purines using a new catalyst of cesium chloride. Heterocycles 1990, 31, 211–214
   Web of Science ®Google Scholar
• Katagiri, N.; Tomura, M.; Haneda, T.; Kaneko, C. Stereospecific synthesis of carbocyclic analogue of oxazinomycin by retrograde aldol C–C bond fission under reductive conditions. J. Chem. Soc. Chem. Commun. 1987, 19, 1422–1423
   Google Scholar
• Coockson, R.C.; Dufield, P.J.; Scopes, D.I.C. Synthesis of carbocyclic C-nucleoside analogues from 8,9,10-trinorborn-5-en-2-ol. J. Chem. Soc. Perkin Trans. 1986, 1, 393–398
   Google Scholar
• Takahashi, T.; Kotsubo, H.; Koizumi, T. Enantioselective synthesis of carbocyclic showdomycin derivative via asymmetric diels-alder reaction of (S)-3-(2-pyridylsulphinyl) acrylate. Tetrahedron Asymmetry 1991, 2, 1035–1040
   Web of Science ®Google Scholar
• Zhou, J.; Yang, M.; Schnell, S.W. A model study to carbocyclic formycin A and B analogues. Tetrahedron Lett. 2004, 45, 8233–8234.
   Web of Science ®Google Scholar
• Kim, S.; Kim, E.; Yoo, J.C.; Hong, J.H. Efficient synthesis of novel 4′-trifluoromethyl-5′-norcarbocyclic purine phosphonic acid analogs by using the Ruppert–Prakash reacrion. Bull. Korean Chem. Soc. 2014, 35, 2743–2748.
   Web of Science ®Google Scholar
• Robins, M.J.; Samano, V.; Johnson, M.D. Periodinane oxidation, selective primary deprotection, and remarkably stereoselective reduction of tert-butyldimethylsilyl-protected ribonucleosides. Synthesis of 9-(β-D-xylofuranosyl)adenine or 3′-deuterioadenosine from adenosine. J. Org. Chem. 1990, 55, 410–412.
   Web of Science ®Google Scholar
• Dess, D.B.; Martin, J.C. A useful 12-I-5 triacetoxyperiodinane (the Dess–Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species. J. Am. Chem. Soc. 1991, 113, 7277–7287.
   Web of Science ®Google Scholar
• Chun, B.K.; Song, G.Y.; Chu, C.K. Stereo-controlled syntheses of carbocyclic C-nucleosides and related compounds. J. Org. Chem. 2001, 66, 4852–4858.
   PubMed Web of Science ®Google Scholar
• Lim, M.I.; Klein, R.S. Synthesis of “9-deazaadenosine”; a new cytotoxic C-nucleoside isostere of adenosine. Tetrahedron Lett. 1981, 22, 25–28.
   Web of Science ®Google Scholar
• Kamath, V.P.; Ananth, S.; Bantia, S.; Morris, P.E. Synthesis of a potent transition-state inhibitor of 5′-deoxy-5′-methylthioadenosine phosphorylase. J. Med. Chem. 2004, 47, 1322–1324.
   PubMed Web of Science ®Google Scholar
• Hubert, E.W.; Kane, J.M.; Dalton, C.R. H-{19F} NOE difference spectroscopy as a tool for structural assignment of positional isomers in fluorine-substituted analogues of FPR 64176. J. Fluorine. Chem. 1997, 82, 47–50
   Web of Science ®Google Scholar
• Miyake, T.; Koyama, Y. Interunit, through-space 1H-19F and 13C-19F spin-spin couplings of 5-fluorinated arbekacins. Carbohydr. Res. 1994, 258, 11–26.
   PubMed Web of Science ®Google Scholar
• Rao, K.V.B.; Ren, W.-Y.; Burchenal, J.H.; Klein, R.S. Synthetic modification at the 2′-position of pyrrolo[3,2-d]pyrimidine and thieno[3,2-d]pyrimidine C-nucleosides, synthesis of “2′-deoxy-9-deazaadenosine” and of “9-deaza ara-A” Nucleosides Nucleotides 1986, 5, 539–569.
   Web of Science ®Google Scholar
• Phillion, D.P.; Andrew, S.S. Synthesis and reactivity of diethyl phosphonomethyltriflate. Tetrahedron Lett. 1986, 27, 1477–1480
   Web of Science ®Google Scholar
• Xu, Y.; Flavin, M.T.; Xu, Z.-Q. Preparation of new Wittig reagents and their application to the synthesis of α,β-unsaturated phosphonates. J. Org. Chem. 1996, 61, 7697–7701.
   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
• Bhattacharya, B.K.; Otter, B.A.; Berens, R.L.; Klein, R.S. Studies on the synthesis of furo[3,2-d]pyrimidine C-nucleosides: new inosine analogues with antiprotozoan activity. Nucleosides Nucleotides 1990, 9, 1021–1043.
   Web of Science ®Google Scholar
• Holy, A.; Votruba, I.; Merta, A.; Cerny, J.; Vesely, J.; Vlach, J.; Sediva, K.; Rosenberg, I.; Otmar, M.; Hrebabecky, H.; Travniekb, M.; Vonkac, V.; Snoeck, R.; De Clercq, E. Acyclic nucleotide analogues: Synthesis, antiviral activity and inhibitory effects on some cellular and virus-encoded enzymes in vitro. Antiviral Res. 1990, 13, 295–311.
   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
• Fischer, G.A. Studies of the culture of leukemic cells in vitro. Ann. N. Y. Acad. Sci. 1958, 76, 673–680.
   PubMed Web of Science ®Google Scholar
• Burchenal, J.H.; Chou, T.-C.; Lokye, L.; Smith, R.S.; Watanabe, K.A.; Su, T.-L.; Fox, J.J. Activity of 2-fluoro-5-methylarabinofuranosyluracil against mouse leukemias sensitive to and resistant to 1-β-D-arabinofuranosylcytosine. Cancer Res. 1982, 42, 2598–2600.
   PubMed Web of Science ®Google Scholar