References
- D. Vina, T. Wu, M. Renders, G. Laflamme, and P. Herdewijn, "Synthesis of 3'-O-phosphonomethyl nucleosides with an adenine base moiety", Tetrahedron, Vol. 63, pp. 2634-2646, 2007. https://doi.org/10.1016/j.tet.2007.01.032
- E. I. Kodama, S. Kohgo, K. Kitano, H. Machida, H. Gatanaga, S. Shigeta, M. Matsuoka, H. Ohrui, and H. Mitsuya, "4'-Ethynyl nucleoside analogs: potent inhibitors of multidrug-resistant human immunodeficiency virus variants in vitro", Antimicrob. Agents Chemother., Vol. 45, pp. 1539-1546, 2001. https://doi.org/10.1128/AAC.45.5.1539-1546.2001
-
S. G. Dumbre, M.-Y. Jang, and P. Herdewijn, "Synthesis of
${\alpha}$ -L-threose nucleoside phosphonates via regioselective sugar protection", J. Org. Chem., Vol. 78, pp. 7137-7144, 2013. https://doi.org/10.1021/jo400907g - U. Pradere, E. C. Garnier-Amblard, S. J. Coats, F. Amblard, and R. F. Schinazi, "Synthesis of nucleoside phosphate and phosphonate prodrugs", Chem. Rev., Vol. 114, pp. 9154-9218, 2014 https://doi.org/10.1021/cr5002035
- R. Engel, "Phosphonates as analogues of natural phosphates", Chem. Rev., Vol. 77, pp. 349-367, 1977 https://doi.org/10.1021/cr60307a003
- O. Baszczy ski, and Z. Janeba, "Medicinal chemistry of fluorinated cyclic and acyclic nucleoside phosphonates", Med. Chem. Rev., Vol. 33, pp. 1304-1344, 2013
- E. De Clercq, "The holy trinity: the acyclic nucleoside phosphonates", Adv. Pharmacol., Vol. 67, pp. 293-316, 2013. https://doi.org/10.1016/B978-0-12-405880-4.00008-1
-
G. M. Blackburn, and D. E. Kent, "Synthesis of
${\alpha}$ - and${\gamma}$ -fluoroalkylphosphonates", J. Chem. Soc., Perkin Trans. 1, pp. 913-917, 1986 - G. R. J. Thatcher, and A. S. Campbell, "Phosphonates as mimics of phosphate biomolecules: ab initio calculations on tetrahedral ground states and pentacoordinate intermediates for phosphoryl transfer", J. Org. Chem., Vol. 58, pp. 2272-2281, 1993 https://doi.org/10.1021/jo00060a050
- T. R Jr. Burke, M. S. Smyth, A. Otaka, M. Nomizu, M.; P. P. Roller, G. Wolf, R. Case, and S. E. Shoelson, "Nonhydrolyzable phosphotyrosyl mimetics for the preparation of phosphatase-resistant SH2 domain inhibitors", Biochemistry, Vol. 33, pp. 6490-6494, 1994. https://doi.org/10.1021/bi00187a015
- R. D. Chambers, R. Jaouhari, and D. O'Hagan, "The preparation of difluoromethylenephosphonate analogues of glycolytic phosphates. Approaching an isosteric and isoelectronic phosphate mimic", Tetrahedron, Vol. 45, pp. 5101-5108, 1989 https://doi.org/10.1016/S0040-4020(01)81089-9
-
D. B. Berkowitz, H. J. Eggen, Q. Shen, and R. K. Shoemaker, "Ready access to fluorinated phosphonate mimics of secondary phosphates. Synthesis of the (
${\alpha},{\alpha}$ -difluoroalkyl) phosphonate analogues of L-phosphoserine, L-phosphoallothreonine, and L-phosphothreonine", J. Org. Chem., Vol. 91, pp. 4666-4675, 1996 - D. J. Burton, Z.-Y. Yang, and W. Qiu, "Fluorinated ylides and related compounds", Chem. Rev., Vol. 96, pp. 1641-1715, 1996. https://doi.org/10.1021/cr941140s
- S. Halazy, A. Ehrhard, and C. Danzin, "(9-(Difluorophosphonoalkyl)guanines as a new class of multisubstrate analogue inhibitors of purine nucleoside phosphorylase", J. Am. Chem. Soc., Vol. 113, pp. 315-317, 1991. https://doi.org/10.1021/ja00001a045
- S. G. Levy, D. B. Wasson, D. A. Carson, and H. B Cottam, "Synthesis of 2-chloro-2',5'-dideoxy-5'-(phosphinyldifluoromethyl)adenosine: A nonhydrolyzable isosteric, isopolar analog of 2-chlorodeoxyadenosine monophosphate", Synthesis, Vol. 7, pp. 843-846, 1996.
- D. A. Fort, T. J. Woltering, A. M. Alker, and T. Bach, "Photochemical reactions of prop-2-enyl and prop-2-ynyl substituted 4-aminomethyl- and 4-oxymethyl-2(5H)-furanones", Heterocycles, Vol. 88, pp. 1079-1100, 2004.
- E. J. Corey, and A.Venkateswarlu, "Protection of hydroxyl groups as t-butyldimethylsilyl derivatives", J. Am. Chem. Soc., Vol. 94, pp. 6190-6172, 1972. https://doi.org/10.1021/ja00772a043
- G. Rassu, F. Zanardi, L. Battistini, E. Caetani, and G. Casirsghi, "Expeditious synthesis of sugarmodified nucleosides and collections thereof exploiting furan-, pyrrole-, and thiophen-based dienes", J. Med. Chem., Vol. 40, pp. 168-180, 1997. https://doi.org/10.1021/jm960400q
-
D. B. Berkowitz, M. Eggen, Q. Shen, and D. G. Sloss, "Synthesis of (
${\alpha},{\alpha}$ ,-difluoroalkyl) phosphonates by displacement of primary triflates", J. Org. chem., Vol. 58, pp. 6174-6176, 1993. https://doi.org/10.1021/jo00075a005 - K. Walczak, J. Lau, and E. B. Pedesen, "2,3,6-Trideoxy-5-O-(4-nitrobenzoyl)-3-trifluoroacetamido-L-ribo-hexofuranosyl bromide - A suitable furanoid ristosamine glycosylation reagent", Synthesis, pp. 790-792, 1993.
- H. Vorbruggen, "Nucleoside analogs, Chemistry", Biology and Medical Applications, NATO ASI Series A 26; Plenum Press: New Tork, pp. 35, 1980.
- D. Hockova, A. Holy, M. Masojidkova, D. T. Keough, J. De Jersey, and L. W. Guddat, "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., Vol. 17, pp. 6218-6232, 2009; https://doi.org/10.1016/j.bmc.2009.07.044
- J. Matulic-Adamic, P. Haeberli, and N. Usman, "Synthesis of 5'-deoxy-difluoromethyl phosphonate nucleoside analogs", J. Org. Chem. Vol. 60, pp. 2563-2569, 1995. https://doi.org/10.1021/jo00113a040
- M. J. Robins, and B. Uznanski, "Non-aqueous diazotization with t-butyl nitrite. Introduction of fluorine, chlorine, and bromine at C-2 of purine nucleoside", Can. J. Chem. Vol. 59, pp. 2608-2611, 1981. https://doi.org/10.1139/v81-375
- J. Montgomery, and K. Hewson, "Nucleosides of 2-fluoroadenine", J. Med. Chem., Vol. 12, pp. 498-504, 1969. https://doi.org/10.1021/jm00303a605
- G. L. Tong, K. J. Ryan, W. W. Lee, E. M. Acton, and L. Goodman, "Nucleosides of thioguanine and other 2-amino-6-substituted purines from 2-acetamido-5-chloropurine", J. Org. Chem., Vol. 32, pp. 859-862, 1967. https://doi.org/10.1021/jo01278a095
- A. Holy, I. Votruba, A. Merta, J. Cerny, J. Vesely, J. Vlach, K. Sediva, I. Rosenberg, M. Otmar, H. Hrebabecky, M. Travniekb, V. Vonkac, R. Snoeck, and E. De Clercq, "Acyclic nucleotide analogues: synthesis, antiviral activity and inhibitory effects on some cellular and virus-encoded enzymes in vitro", Antiviral Res., Vol. 13, pp. 295-311, 1990. https://doi.org/10.1016/0166-3542(90)90014-X
- O. H. Ko, and J. H. Hong, "Synthesis and biological evaluation of novel 2',3'-4'-triply branched carbocyclic nucleosides as potential antiviral agents", Arch. Pharm. Pharm. Med. Chem., Vol. 337, pp. 579-586, 2004. https://doi.org/10.1002/ardp.200400918