Synthesis and biological activity of 4'-thio analogs of the antibiotic toyocamycin

Bobek, M.; Rl, Whistler; Aa, Bloch

doi:10.1021/jm00272a011

Cited by 49 publications

(21 citation statements)

References 3 publications

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“…Later on, Bobek and co-workers used the chloromercuric procedure for the preparation of 7-deazapurine 4'thioribonucleosides [50]. The reaction of the mercuric salt 28a with the 2,3,5-tri-O-acetyl-4-thio-D-ribofuranosyl chlo-Scheme (4).…”

Section: The Metal Salt Proceduresmentioning

confidence: 99%

Progress in 7-Deazapurine - Pyrrolo[2,3-d]pyrimidine - Ribonucleoside Synthesis

Seela¹,

Peng

2006

CTMC

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This review reports on the synthesis of 7-deazapurine ribonucleosides, including C-nucleosides, 2'-C-methyl derivatives and L-enantiomers. It covers the various aspects of convergent nucleoside synthesis such as the Schiff base procedure, the fusion reaction, the metal salt procedures, the Silyl-Hilbert-Johnson reaction, and the nucleobase anion glycosylation. The review discusses the scope and limitations of glycosylation reactions performed on 7-deazapurines. Peracylated ribose derivatives were now employed in the glycosylation, which overcome difficulties reported earlier.

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Section: The Metal Salt Proceduresmentioning

confidence: 99%

Progress in 7-Deazapurine - Pyrrolo[2,3-d]pyrimidine - Ribonucleoside Synthesis

Seela¹,

Peng

2006

CTMC

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“…7 The effect of toyocamycin derivatives on the growth of Streptococcus faecium is sumarized in Table 2. 8 The 4'thiotoyocamycin, 26 was approximately 10 times more effective an inhibitor than toyocamycin, while the 6-amino derivative 27 was 2 times more potent. The 6-Br derivative was inactive at 10 -3 .…”

Section: Scheme 34mentioning

confidence: 96%

Synthesis and Biological Activity of Thionucleosides

Yokoyama¹

2000

Synthesis

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In recent years nucleosides and nucleotides known to be DNA and RNA subunits have become an increasingly important subject of research in the field of pharmaceutical science. In particular, recent studies deal with the synthesis and biological activity of novel types of nucleosides and nucleotides. Herein, the chemistry of the so-called thionucleosides which have the thiofuranosyl and thioxofuranosyl moieties, and show potent biological activities will be summarized, together with our recent work in this area.

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“…When used in combination with the corresponding ribosyl analogues, the thioribosyl derivatives tested interfered with the growth of S. faecium in a synergistic manner [5]. The effects of toyocamycin derivatives on the growth of S. faecium are summarized in Table 8.2 [6]. …”

Section: Biological Activity Of Thionucleosidesmentioning

confidence: 99%

The Properties of 4′‐Thionucleosides

Yokoyama

2008

Modified Nucleosides

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Synthesis and biological activity of 4'-thio analogs of the antibiotic toyocamycin

Cited by 49 publications

References 3 publications

Progress in 7-Deazapurine - Pyrrolo[2,3-d]pyrimidine - Ribonucleoside Synthesis

Progress in 7-Deazapurine - Pyrrolo[2,3-d]pyrimidine - Ribonucleoside Synthesis

Synthesis and Biological Activity of Thionucleosides

The Properties of 4′‐Thionucleosides

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