Synthesis and biological evaluation of lipophilic teicoplanin pseudoaglycon derivatives containing a substituted triazole function
A series of lipophilic teicoplanin pseudoaglycon derivatives, including alkyl-, aryl-, calixarene- and protected sugar-containing conjugates, were prepared using azide–alkyne click chemistry. Out of the conditions applied, the CuSO 4 –ascorbate reagent system proved to be more efficient than the Cu(...
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| Veröffentlicht in: | Journal of antibiotics 2017-02, Vol.70 (2), p.152-157 |
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| container_title | Journal of antibiotics |
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| creator | Szűcs, Zsolt Csávás, Magdolna Rőth, Erzsébet Borbás, Anikó Batta, Gyula Perret, Florent Ostorházi, Eszter Szatmári, Réka Vanderlinden, Evelien Naesens, Lieve Herczegh, Pál |
| description | A series of lipophilic teicoplanin pseudoaglycon derivatives, including alkyl-, aryl-, calixarene- and protected sugar-containing conjugates, were prepared using azide–alkyne click chemistry. Out of the conditions applied, the CuSO
4
–ascorbate reagent system proved to be more efficient than the Cu(I)I–Et
3
N-mediated reaction. Some of the new compounds have high
in vitro
activity against glycopeptide-resistant Gram-positive bacteria, including vanA-positive
Enterococcus faecalis
. A few of them also display promising
in vitro
anti-influenza activity. |
| doi_str_mv | 10.1038/ja.2016.80 |
| format | Article |
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4
–ascorbate reagent system proved to be more efficient than the Cu(I)I–Et
3
N-mediated reaction. Some of the new compounds have high
in vitro
activity against glycopeptide-resistant Gram-positive bacteria, including vanA-positive
Enterococcus faecalis
. A few of them also display promising
in vitro
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4
–ascorbate reagent system proved to be more efficient than the Cu(I)I–Et
3
N-mediated reaction. Some of the new compounds have high
in vitro
activity against glycopeptide-resistant Gram-positive bacteria, including vanA-positive
Enterococcus faecalis
. A few of them also display promising
in vitro
anti-influenza activity.</description><subject>639/638/309/2144</subject><subject>692/308/153</subject><subject>Alkynes</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antifungal agents</subject><subject>Ascorbic acid</subject><subject>Bacteria</subject><subject>Bacteria - drug effects</subject><subject>Bacteriology</subject><subject>Biomedical and Life Sciences</subject><subject>Bioorganic Chemistry</subject><subject>Calixarenes</subject><subject>Chemical synthesis</subject><subject>Drug Resistance, Bacterial</subject><subject>Glycopeptides</subject><subject>Gram-positive bacteria</subject><subject>Influenza</subject><subject>Life Sciences</subject><subject>Lipophilic</subject><subject>Lipophilicity</subject><subject>Medicinal Chemistry</subject><subject>Microbial Sensitivity Tests</subject><subject>Microbiology</subject><subject>Molecular Structure</subject><subject>Organic Chemistry</subject><subject>original-article</subject><subject>Reagents</subject><subject>Teicoplanin</subject><subject>Teicoplanin - 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Academic</collection><jtitle>Journal of antibiotics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Szűcs, Zsolt</au><au>Csávás, Magdolna</au><au>Rőth, Erzsébet</au><au>Borbás, Anikó</au><au>Batta, Gyula</au><au>Perret, Florent</au><au>Ostorházi, Eszter</au><au>Szatmári, Réka</au><au>Vanderlinden, Evelien</au><au>Naesens, Lieve</au><au>Herczegh, Pál</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and biological evaluation of lipophilic teicoplanin pseudoaglycon derivatives containing a substituted triazole function</atitle><jtitle>Journal of antibiotics</jtitle><stitle>J Antibiot</stitle><addtitle>J Antibiot (Tokyo)</addtitle><date>2017-02-01</date><risdate>2017</risdate><volume>70</volume><issue>2</issue><spage>152</spage><epage>157</epage><pages>152-157</pages><issn>0021-8820</issn><eissn>1881-1469</eissn><abstract>A series of lipophilic teicoplanin pseudoaglycon derivatives, including alkyl-, aryl-, calixarene- and protected sugar-containing conjugates, were prepared using azide–alkyne click chemistry. Out of the conditions applied, the CuSO
4
–ascorbate reagent system proved to be more efficient than the Cu(I)I–Et
3
N-mediated reaction. Some of the new compounds have high
in vitro
activity against glycopeptide-resistant Gram-positive bacteria, including vanA-positive
Enterococcus faecalis
. A few of them also display promising
in vitro
anti-influenza activity.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><pmid>27353163</pmid><doi>10.1038/ja.2016.80</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
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| ispartof | Journal of antibiotics, 2017-02, Vol.70 (2), p.152-157 |
| issn | 0021-8820 1881-1469 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1826708268 |
| source | MEDLINE; Alma/SFX Local Collection; EZB Electronic Journals Library |
| subjects | 639/638/309/2144 692/308/153 Alkynes Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - pharmacology Antifungal agents Ascorbic acid Bacteria Bacteria - drug effects Bacteriology Biomedical and Life Sciences Bioorganic Chemistry Calixarenes Chemical synthesis Drug Resistance, Bacterial Glycopeptides Gram-positive bacteria Influenza Life Sciences Lipophilic Lipophilicity Medicinal Chemistry Microbial Sensitivity Tests Microbiology Molecular Structure Organic Chemistry original-article Reagents Teicoplanin Teicoplanin - analogs & derivatives Teicoplanin - chemical synthesis Teicoplanin - pharmacology Triazoles - chemistry |
| title | Synthesis and biological evaluation of lipophilic teicoplanin pseudoaglycon derivatives containing a substituted triazole function |
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