4-Thio-D-arabinofuranosylpyrimidine nucleosides

Rl, Whistler; Lw, Doner; Ug, Nayak

doi:10.1021/jo00800a023

Cited by 33 publications

(19 citation statements)

References 2 publications

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“…The separated water phase was concentrated under reduced pressure. The residue was purified on column chromatography over silica gel (10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20), and the anomers were separated by HPLC (YMC-PACK SIL-06 20 × 250mm, YMC Co., Ltd., Japan; 7% MeOH in CHCl3, flow rate 7 mL/min; retention time R, 23 min, , 22 min) to give R-6a (34 mg, 24%) and -6a (12 mg 5-Iodo-1-(4-thio-D-arabinofuranosyl)uracil (6c). From 11 (503 mg, 1.05 mmol), R-and -4c were obtained as described in the synthesis of 6a.…”

Section: -Ethyl-1-(4-thio-d-arabinofuranosyl)uracil (6a)mentioning

confidence: 99%

A Facile, Alternative Synthesis of 4‘-Thioarabinonucleosides and Their Biological Activities

et al. 1997

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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 hydroxyl groups to give 1-O-acetyl-4-thioarabinose (11), which was condensed with nucleobases to give 4'-thioarabinonucleosides. The 5-substituted-4'-thioaraU (6a-e) derivatives showed anti-HSV-1 activity (ED50 = 0.43-3.50 micrograms/mL). 4'-ThioaraG (6h) and 2,6-diaminopurine 4'-thioarabinonucleoside (4'-thioaraDAP, 6g) showed antiviral activity against several herpes viruses and were particularly potent against human cytomegalovirus (0.010 and 0.022 microgram/mL, respectively).

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Section: -Ethyl-1-(4-thio-d-arabinofuranosyl)uracil (6a)mentioning

confidence: 99%

A Facile, Alternative Synthesis of 4‘-Thioarabinonucleosides and Their Biological Activities

et al. 1997

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“…The synthesis of 4Ј-thio-␤-D-arabinofuranosyl cytosine (TaraC) was reported more than 30 years ago (Whistler et al, 1971). In recent studies (Waud et al, 2003), TaraC and araC were evaluated for activity against a panel of human tumor cell lines.…”

mentioning

confidence: 99%

The Role of Human Nucleoside Transporters in Cellular Uptake of 4′-Thio-β-d-arabinofuranosylcytosine and β-d-Arabinosylcytosine

Clarke¹,

Damaraju²,

Zhang³

et al. 2006

Molecular Pharmacology

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combinant transporters (produced in yeast) for a panel of cytosine-containing nucleosides yielded results that were consistent with the observed low-permeant activities of TaraC and araC for hENT1/2 and negligible permeant activities for hCNT1/ 2/3. During prolonged drug exposures of CEM cells with hENT1 activity, araC was more cytotoxic than TaraC, whereas coexposures with nitrobenzylthioinosine (to pharmacologically block hENT1) yielded identical cytotoxicities for araC and TaraC. The introduction by gene transfer of hENT2 and hCNT1 activities, respectively, into nucleoside transport-defective CEM cells increased sensitivity to both drugs moderately and slightly. These results demonstrated that nucleoside transport capacity (primarily via hENT1, to a lesser extent by hENT2 and possibly by hCNT1) is a determinant of pharmacological activity of both drugs.

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“…To our knowledge, at the time that we began this project, the only 4′-thionucleosides that had been synthesized were 4′-thioribonucleosides, [17][18][19] 4′-thioarabinonucleosides [20][21][22] and 2′-deoxy-4′-thionucleosdes. 13,14) The development of a synthetic strategy for 4′-thionucleosides applicable to the synthesis of 2′-substituted derivatives was thus a key to the success of this project.…”

Section: Development Of Pummerer-type Glycosylation and Its Applicatimentioning

confidence: 99%

Synthesis of 4′-Thionucleosides as Antitumor and Antiviral Agents

Yoshimura

Saito

Natori

et al. 2018

CHEMICAL & PHARMACEUTICAL BULLETIN

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Many attempts have been made to synthesize structurally novel nucleoside derivatives in order to identify effective compounds for the treatment of tumors and virus-caused disease. At our laboratories, as part of our efforts to synthesize 4′-thionucleosides, we have identified and characterized biologically active nucleosides. During the course of our synthetic study, we developed the Pummerer-type thioglycosylation reaction. As a result, we synthesized a potent antineoplastic nucleoside, 1-(2-deoxy-2-fluoro-β-D-4-thio-arabinofuranosyl)cytosine (4′-thioFAC), and several novel 4′-thionucleosides that possess antiherpes virus activities.

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4-Thio-D-arabinofuranosylpyrimidine nucleosides

Cited by 33 publications

References 2 publications

A Facile, Alternative Synthesis of 4‘-Thioarabinonucleosides and Their Biological Activities

A Facile, Alternative Synthesis of 4‘-Thioarabinonucleosides and Their Biological Activities

The Role of Human Nucleoside Transporters in Cellular Uptake of 4′-Thio-β-d-arabinofuranosylcytosine and β-d-Arabinosylcytosine

Synthesis of 4′-Thionucleosides as Antitumor and Antiviral Agents

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