- 4'-thio-L-xylofuranosyl nucleosides, precursors thereof, preparation and use thereof
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Compounds represented by the formula 1: A is selected from the group consisting of wherein each R individually is H or acyl, Y is X, N3, NH2, monoalkylamino, or dialkylamino; Z is O or S; and X is selected from the group consisting o
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- Thiosugars. VIII. Preparation of new 4′-thio-L-lyxo pyrimidine nucleoside analogues
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Reaction of 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-L-lyxofuranose with silylated pyrimidine bases and subsequent deprotection with boron tribromide led to 4′-thio-L-lyxo pyrimidine nucleosides. The 5-bromo-6-methyl derivative was prepared from methyl 2,3,5-
- Wirsching, Joern,Voss, Juergen,Adiwidjaja, Gunadi,Balzarini, Jan,De Clercq, Erik
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p. 1625 - 1645
(2007/10/03)
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- Synthesis and biological activity of 4′-thio-L-xylofuranosyl nucleosides
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A series of 4′-thio-L-xylofuranosyl nucleosides were prepared and evaluated as potential anticancer and antiviral agents. The details of a convenient and high-yielding synthesis of the carbohydrate precursor 1-O-acetyl-2,3,5-tri-O-benzyl-4- thio-L-xylofuranose (6) are presented. Proof of structure and configuration at all chiral centers of the nucleosides was obtained by proton and carbon NMR. All target compounds were evaluated in a series of human cancer cell lines in culture and as antiviral agents.
- Tiwari,Messini,Montgomery,Secrist III
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p. 743 - 746
(2007/10/03)
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- Thiosugars, 2: Preparation of 2,3,5-tri-O-benzyl-4-thio-L-arabino- furanosides and the corresponding 4'-thionucleoside analogues
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1-O-Acetyl-2,3,5-tri-O-benzyl-4-thio-L-arabino-furanose (9) has been prepared from D-xylose via the 1,4-dithio-L-arabino-furanoside 8. The crucial step of the reaction, i.e. the intramolecular cyclization of the open-chain dithioacetal 5, has been achieved in a yield of 90% by applying tetrabutylammonium iodide as promoter. Reaction of 9 with bis(trimethylsilyl)uracil or -thymine led to the benzyl derivatives 12 and 13 from which the deprotected 4'-thionucleoside analogues 14 and 15 have been prepared by debenzylation with boron tribromide.
- Wirsching, Joern,Voss, Juergen
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p. 691 - 696
(2007/10/03)
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- Synthesis of L-enantiomers of 4'-thioarabinofuranosyl pyrimidine nucleosides
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L-Enantiomers of 4'-thioarabinofuranosyl pyrimidine nucleosides were synthesized from D-xylose. Methyl 2,3,5-tri-O-benzyl-D-xylofuranoside 6 was converted to the corresponding xylitol 7, which was treated with MsCl and then Na2S to give 1,4-anhydro-L-4-thioarabitol 8. As previously reported, Pummerer rearrangement of 8 followed by glycosylation with a silylated thymine and N4-acetylcytosine derivative and deprotection gave the corresponding α- and β-L-4'-thioarabinofuranosyl pyrimidine nucleosides.
- Satoh, Hiroshi,Yoshimura, Yuichi,Sakata, Shinji,Miura, Shinji,Machida, Haruhiko,Matsuda, Akira
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p. 989 - 992
(2007/10/03)
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- A facile, alternative synthesis of 4'-thioarabinonucleosides and their biological activities
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4'-Thioarabinonucleosides, which are potential antiviral agents, were synthesized from D-glucose. 1,4-Anhydro-4-thioarabitol (8), which can be derived from diacetone glucose in nine steps, was subjected to Pummerer rearrangement after protection of the hy
- Yoshimura, Yuichi,Watanabe, Mikari,Satoh, Hiroshi,Ashida, Noriyuki,Ijichi, Katsushi,Sakata, Shinji,Machida, Haruhiko,Matsuda, Akira
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p. 2177 - 2183
(2007/10/03)
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- Synthesis and biological activities of 2'-modified 4'-thionucleosides
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We have synthesized 4'-thioDMDC, 4'-thiogemcitabine, and 4'- thioarabinonucleosides, as potential antitumor and antiviral agents, originated from D-glucose. Biological activities of these compounds are also described.
- Yoshimura, Yuichi,Kitano, Kenji,Watanabe, Mikari,Satoh, Hiroshi,Sakata, Shinji,Miura, Shinji,Ashida, Noriyuki,Machida, Haruhiko,Matsuda, Akira
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p. 1103 - 1106
(2007/10/03)
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- 4'-Thio-β-D-oligoribonucleotides: Nuclease resistance and hydrogen bonding properties
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The syntheses and the study of nuclease resistance and hydrogen bonding of modified oligoribonucleotides, i.e. 4'-thio-β-D-oligoribonucleotides (4'-S-RNA), are reported.
- Leydier,Bellon,Barascut,Imbach
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p. 1027 - 1030
(2007/10/02)
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