Nucleosides. V. 2-Thiopyrimidine β-<scp>D</scp>-Arabinofuranosides

Ruyle, W. V.; Shen, T. Y.

doi:10.1021/jm00315a009

Cited by 33 publications

(8 citation statements)

References 3 publications

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“…The synthetic procedures for the 2-thiopyrimidine nucleoside analogues have been reported by several groups, however there are very few reports of antiviral activity of these compounds. 2thiouracil is known to be a growth inhibitor of some plant viruses (Dawson & Grantham, 1983;Kuhn, 1977;Ralph & Wojcik, 1976) but reports of its inhibitory activities against animal viruses are limited to a few papers in which 2thiouracil inactivated polioviruses and 1-β-D-arabinofuranosyl-2-thiocytosine inhibited the growth of vaccinia virus in tissue culture cells (Steele & Black, 1967;Ruyle & Shen, 1967). It is well known that 2-thiouracil or uridine is utilized in the anticodon of tRNA in bacterial and fungal cells.…”

Section: Discussionmentioning

confidence: 99%

“…The previous method used to obtain 2-thiopyrimidine arabinosides (Ruyle et al, 1967;Sekiya et al, 1967) was anhydro-ring cleavage of 2,2′-anhydronucleosides with hydrogen sulphide in the presence of a weak base. Arabinofuranosyl-2-thiothymine (TN-18) and arabinofuranosyl 2-thiouracil were prepared in this manner at a 68% and 75% yield, respectively.…”

Section: Materials and Methods: Chemistrymentioning

confidence: 99%

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Anti-Herpesvirus Activities and Cytotoxicities of 2-Thiopyrimidine Nucleoside Analogues in Vitro

Shigeta

Mori

Kira

et al. 1999

Antivir Chem Chemother

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Twenty 2-thiopyrimidine nucleoside analogues were synthesized and examined for inhibitory activity against herpes simplex virus (HSV) type 1 and 2, varicella-zoster virus (VZV), human cytomegalovirus (HCMV) and thymidine kinase-deficient HSV (HSV-TK-) replication in vitro. 2-thiouracil (thymine) arabinoside, 2'-deoxy-2-thiouridine (or 2-thiothymidine) and their 5-halogenated derivatives showed anti-HSV activity in both RPM18226 (human B-lymphoblastoid cells) and MRC-5 (human embryo lung cells). 2'-deoxy-5-halogenated-2-thiocytidines were also inhibitory against HSV, whereas 2-thiocytosine arabinoside and its derivatives were not inhibitory against HSV replication, except 5-bromo and 5-iodo congeners (TN-31, TN-32). Substitution of the halogen atom at the 5-position of the pyrimidine rings to an atom with a higher molecular weight increased anti-HSV and VZV activities, except for the anti-HSV activity of 2-thiouracil arabinosides. 2'-deoxy-5-methyl-, and 2'-deoxy-5-iodo-2-thiouridines (TN-17, TN-44) showed the most potent anti-HSV activity, and 2'-deoxy-5-chloro- and 2'-deoxy-5-bromo-2-thiocytidines were potent inhibitors of VZV replication. However, none of the compounds inhibited HCMV and HSV-TK- replication. TN-31 and TN-32 were shown to inhibited HCMV and HSV-TK- as well as HSV and VZV replication. The cytotoxicity of the 2-thio-pyrimidine nucleoside analogues was less than that of the 2-oxy-congeners of the compounds (5-iodo-2'-deoxyuridine, 5-iodo-2'-deoxycytidine, thymine arabinoside and cytosine arabinoside). The selectivity index of 2'-deoxy-5-iodo-2-thiouridine (TN-44) was higher than that of 5-iodo-deoxyuridine. TN-17 and TN-44 were not cytotoxic to resting or stimulated human peripheral blood mononuclear cells at 400 microM, although TN-32 was cytotoxic at a concentration of 20 microM.

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Section: Discussionmentioning

confidence: 99%

Section: Materials and Methods: Chemistrymentioning

confidence: 99%

Anti-Herpesvirus Activities and Cytotoxicities of 2-Thiopyrimidine Nucleoside Analogues in Vitro

Shigeta

Mori

Kira

et al. 1999

Antivir Chem Chemother

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“…The thiocytosine tautomers base have been found in Escherichia coli tRNA [43][44][45]. Its nucleosides exhibit moderate inhibitory activity against vaccine and Epstein-Barr viruses in cell cultures and fluorinated 2-thiocytidine has shown potent antileukemic activity [46][47][48]. Substitution of oxygen in a carbonyl group of cytosine by selenium causes changes in molecular properties associated with the C=X group.…”

Section: Pilot Studiesmentioning

confidence: 99%

Relativistic study of tautomerism and core electron binding energies of thio- and selenocytosine

2012

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We applied the spin-free relativistic infiniteorder two-component method to calculate the core-electron binding energies of different tautomeric structures of thioand selenocytosine. The importance of relativistic effects in the ionization of 1s electrons was studied for selenocytosine. The present method provides a reasonably simple and reliable computational tool for calculating the core electron binding energies of molecules containing heavy atoms. The method can also be used for characterization of different tautomeric structures of nucleic acid basis.

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“…(364.365) The thiation of 2-thio derivatives of arabinosyluracil(366) or thymidine(367) gave the corresponding 2,4-dithio derivatives.The thiation procedure with solvents other than pyridine was also reported.A mixture of toluene and pyridine was used in the thiation of 5'-O-tritylated uridines. (368.369) The thiation of 3',5'-di-O-benzoyl-06,5'-cyc!ouridine and 3-(2,3,5-tri-O-benzoyl-D-ribosyl)-6-methyluracil, to furnish the respective 4-thio derivatives, was accomplished in dioxane.…”

mentioning

confidence: 99%

Synthesis and Reaction of Pyrimidine Nucleosides

Ueda

1988

Chemistry of Nucleosides and Nucleotides

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Nucleosides. V. 2-Thiopyrimidine β-D-Arabinofuranosides

Cited by 33 publications

References 3 publications

Anti-Herpesvirus Activities and Cytotoxicities of 2-Thiopyrimidine Nucleoside Analogues in Vitro

Anti-Herpesvirus Activities and Cytotoxicities of 2-Thiopyrimidine Nucleoside Analogues in Vitro

Relativistic study of tautomerism and core electron binding energies of thio- and selenocytosine

Synthesis and Reaction of Pyrimidine Nucleosides

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