97614-43-2Relevant articles and documents
Triethylamine poly(hydrogen fluorides) in the synthesis of a fluorinated nucleoside glycon
Chou,Becke, Lisa M.,O'Toole, John C.,Carr, M. Austin,Parker, Bruce E.
, p. 17 - 20 (1996)
The stereospecific synthesis of 6 via a highly selective, noncorrosive fluorination of 4 with Et3N · 3HF was discovered. The intermediate fluorosulfonate 5 was isolated, purified and its structure verified.
Synthesis of DNA oligos containing 2′-deoxy-2′-fluoro-d- arabinofuranosyl-5-carboxylcytosine as hTDG inhibitor
Dai, Qing,Lu, Xingyu,Zhang, Liang,He, Chuan
scheme or table, p. 5145 - 5151 (2012/08/13)
As an important step of the active demethylation of 5-methylcytosine (5mC), human thymine DNA glycosylase (hTDG) efficiently excises 5-carboxylcytosine (5caC) from double-stranded DNA (dsDNA). Here, we present synthesis of DNA oligos containing a 2′-deoxy-2′-fluoro-d-arabinofuranosyl-5- carboxylcytidine (F-5caC) modification that act as hTDG inhibitors. The glycosylase activity assay showed that F-5caC oligos were resistant to excision by the hTDG catalytic domain (hTDGcat, residues 111-308) and they could inhibit the excision of DNA oligos containing 5caC. The electrophoretic mobility shift assay confirmed that DNA oligos containing F-5caC could bind well with unmodified hTDGcat to form a stable complex, which makes it possible to obtain the crystal structure of the complex to reveal details on how hTDGcat recognizes the DNA substrate.
2'-FLUORO-4'-SUBSTITUTED NUCLEOSIDES, THE PREPARATION AND USE
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Page/Page column 11-12, (2010/05/13)
The present invention provides 2'-fluorine-4'-substituted-nucleoside analogues or their pro-drugs or 5'-phosphate esters (including the pro-drugs of the 5'-phosphate esters), preparation methods and uses thereof. The compounds have the general formula as follows: wherein: R = CH3, CH, N3, C≡CH; R' = H, F; X = F, OH, NH2; Y = H, CH3, F, OH, NH2 The compounds are used in the synthesis of drugs for the treatment of virus infection, especially for the treatment of HBV, HCV or HIV infection.
Synthesis and evaluation of [18F] labeled pyrimidine nucleosides for positron emission tomography imaging of herpes simplex virus 1 thymidine kinase gene expression
Pillarsetty, Nagavarakishore,Cai, Shangde,Ageyeva, Lyudmila,Finn, Ronald D.,Blasberg, Ronald G.
, p. 5377 - 5381 (2007/10/03)
Synthesis of three novel 2′-deoxy-2′-[18F]fluoro-1- β-D-arabinofuranosyluracil derivatives [18F]FPAU, [ 18F]-FBrVAU, and [18F]FTMAU is reported. The compounds were synthesized by coupling of 1-bromo-2-deoxy-2-fluoro sugars with corresponding silylated uracil derivatives. In vitro cell uptake indicated that all three compounds are taken up selectively in RG2TK+ cells with negligible uptake in RG2 cells. The results indicate that [18F]FBrVAU and [ 18F]FTMAU have better uptake profiles in comparison to [ 18F]FPAU and have potential as PET probes for imaging HSV1-tk gene expression.
Direct and convenient conversion of alcohols to fluorides
Yin, Jingjun,Zarkowsky, Devin S.,Thomas, David W.,Zhao, Matthew M.,Huffman, Mark A.
, p. 1465 - 1468 (2007/10/03)
Directly mixing primary, secondary, and tertiary alcohols with nC 4F9SO2F-NR3(HF)3-NR 3 in THF or MeCN results in convenient conversion to the corresponding fluorides in high yields. The readily available reagents are easy to handle, and the mild, almost neutral reaction conditions allow for excellent functional group compatibility. A NR3(HF)3/NR3 ratio of ≤ 1:2 gives the highest reactivity.
Synthesis of 2',3'-dideoxy-2'-fluoro-3'-thioarabinothymidine and its 3'-phosphoramidite derivative.
Elzagheid, Mohamed I,Tedeschi, Anna Lisa,Damha, Masad J
, p. 1343 - 1346 (2007/10/03)
An efficient method for the synthesis of 5'-O-monomethoxytrityl-2',3'-dideoxy-2'-fluoro-3'-thioarabinothymidine [(5'MMT)araF-T(3'SH), (5)] and its 3'-phosphoramidite derivative (6) suitable for automated incorporation into oligonucleotides, is demonstrated. A key step in the synthesis involves reaction of 5'-O-MMT-2,3'-O-anhydrothymidine (4) (Eleuteri, A.; Reese, C.B.; Song, Q. J. Chem. Soc. Perkin Trans. 1 1996, 2237 pp.) with sodium thioacetate to give (5'-MMT)araF-T(3'SAc) (5) (Elzagheid, M.I.; Mattila, K.; Oivanen, M.; Jones, B.C.N.M.; Cosstick, Loennberg, H. Eur. J. Org. Chem. 2000, 1987-1991). This nucleoside was then converted to its corresponding phosphoramidite derivative, 6, as described previously ((a) Sun, S.; Yoshida, A.; Piccirilli, J.A. RNA, 1997, 3, 1352-1363; (b) Matulic-Adamic, J.; Beigelman, L. Helvetica Chemica Acta 1999, 82, 2141-2150: (c) Fettes, K.J.; O'Neil, I.; Roberts, S.M.; Cosstick, R. Nucleosides, Nucleotides and Nucl. Acids 2001, 20, 1351-1354).
Synthesis of 2-deoxy-2-fluoro-arabinose derivatives
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, (2008/06/13)
A process for deoxofluorinating a C2-hydroxyl group of a furanose, includes: (a) mixing the furanose and a deoxofluorinating agent in a solvent to form a reaction mixture, and (b) heating the reaction mixture to greater than about 50° C. The process provides deoxofluorinated products, such as 2-fluoro-arabinoses, in yields of at least 80% of theoretical.
Stereospecific fluorination of 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-sulfonate esters: Preparation of a versatile intermediate for synthesis of 2′-[ 18F ]-fluoro-arabinonucleosides
Alauddin, Mian M.,Conti, Peter S.,Mathew, Thomas,Fissekis, John D.,Surya Prakash,Watanabe, Kyoichi A.
, p. 87 - 91 (2007/10/03)
A detailed investigation on fluorination of 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-sulphonate esters is reported. Various combinations of sulfonate esters, fluorinating agents and solvents were evaluated in this study. Organic ammonium fluoride, in particular n-Bu4NF, was found to be better fluorinating agent than inorganic fluoride, and 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-trifluoromethylsulphonate ester appeared to be the best substrate. The developed method is suitable for stereospecific (arabino) incorporation of radiofluorine (18F) into the sugar moiety.
Synthesis and NMR conformational studies of stable analogues of 2-deoxy-α-D-ribose-1-phosphate
Rubira, Maria-Jose,Jimeno, Maria-Luisa,Balzarini, Jan,Camarasa, Maria-Jose,Perez-Perez, Maria-Jesus
, p. 8223 - 8240 (2007/10/03)
Malonate ethers and phosphonate derivatives of 2-deoxyribose and 2-deoxy-2-fluoroarabinose have been synthesized, for the first time, as stable analogues of 2-deoxy-α-D-ribose-1-phosphate (1). In almost all the cases, the α-anomers have been obtained as the major isomers. The NMR conformational analysis performed indicate a similar conformational equilibria for the natural phosphate 1 and the here described analogues, with the exception of the glycosyl phosphonate 3α. None of the compounds were inhibitory to purified E. coli thymidine phosphorylase at 250 μM. Also, when administered to intact CEM cells, no inhibitory effect was observed in hypoxanthine and inosine metabolising enzymes, including purine nucleoside phosphorylase.
