-
Je něco špatně v tomto záznamu ?
Synthesis and biological profiling of 6- or 7-(het)aryl-7-deazapurine 4'-C-methylribonucleosides
P. Nauš, O. Caletková, P. Perlíková, L. Poštová Slavětínská, E. Tloušťová, J. Hodek, J. Weber, P. Džubák, M. Hajdúch, M. Hocek,
Jazyk angličtina Země Anglie, Velká Británie
Typ dokumentu časopisecké články, práce podpořená grantem
- MeSH
- antitumorózní látky chemická syntéza farmakologie MeSH
- antivirové látky chemická syntéza farmakologie MeSH
- Hepacivirus účinky léků MeSH
- lidé MeSH
- nádorové buněčné linie MeSH
- prekurzory léčiv chemická syntéza farmakologie MeSH
- purinové nukleosidy chemická syntéza farmakologie MeSH
- purinové nukleotidy chemická syntéza farmakologie MeSH
- virus dengue účinky léků MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
The synthesis and biological activity profiling of a large series of diverse pyrrolo[2,3-d]pyrimidine 4'-C-methylribonucleosides bearing an (het)aryl group at position 4 or 5 is reported as well as the synthesis of several phosphoramidate prodrugs. These compounds are 4'-C-methyl derivatives of previously reported cytostatic hetaryl-7-deazapurine ribonucleosides. The synthesis is based on glycosylation of halogenated 7-deazapurine bases with 1,2-di-O-acetyl-3,5-di-O-benzyl-4-C-methyl-β-d-ribofuranose followed by cross-coupling and nucleophilic substitution reactions. The final compounds showed low cytotoxicity and several derivatives exerted antiviral activity against HCV or Dengue viruses at micromolar concentrations.
Citace poskytuje Crossref.org
- 000
- 00000naa a2200000 a 4500
- 001
- bmc16027970
- 003
- CZ-PrNML
- 005
- 20161021095520.0
- 007
- ta
- 008
- 161005s2015 enk f 000 0|eng||
- 009
- AR
- 024 7_
- $a 10.1016/j.bmc.2015.10.040 $2 doi
- 024 7_
- $a 10.1016/j.bmc.2015.10.040 $2 doi
- 035 __
- $a (PubMed)26558518
- 040 __
- $a ABA008 $b cze $d ABA008 $e AACR2
- 041 0_
- $a eng
- 044 __
- $a enk
- 100 1_
- $a Nauš, Petr $u Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nam. 2, CZ-16610 Prague 6, Czech Republic.
- 245 10
- $a Synthesis and biological profiling of 6- or 7-(het)aryl-7-deazapurine 4'-C-methylribonucleosides / $c P. Nauš, O. Caletková, P. Perlíková, L. Poštová Slavětínská, E. Tloušťová, J. Hodek, J. Weber, P. Džubák, M. Hajdúch, M. Hocek,
- 520 9_
- $a The synthesis and biological activity profiling of a large series of diverse pyrrolo[2,3-d]pyrimidine 4'-C-methylribonucleosides bearing an (het)aryl group at position 4 or 5 is reported as well as the synthesis of several phosphoramidate prodrugs. These compounds are 4'-C-methyl derivatives of previously reported cytostatic hetaryl-7-deazapurine ribonucleosides. The synthesis is based on glycosylation of halogenated 7-deazapurine bases with 1,2-di-O-acetyl-3,5-di-O-benzyl-4-C-methyl-β-d-ribofuranose followed by cross-coupling and nucleophilic substitution reactions. The final compounds showed low cytotoxicity and several derivatives exerted antiviral activity against HCV or Dengue viruses at micromolar concentrations.
- 650 _2
- $a antitumorózní látky $x chemická syntéza $x farmakologie $7 D000970
- 650 _2
- $a antivirové látky $x chemická syntéza $x farmakologie $7 D000998
- 650 _2
- $a nádorové buněčné linie $7 D045744
- 650 _2
- $a virus dengue $x účinky léků $7 D003716
- 650 _2
- $a Hepacivirus $x účinky léků $7 D016174
- 650 _2
- $a lidé $7 D006801
- 650 _2
- $a prekurzory léčiv $x chemická syntéza $x farmakologie $7 D011355
- 650 _2
- $a purinové nukleosidy $x chemická syntéza $x farmakologie $7 D011684
- 650 _2
- $a purinové nukleotidy $x chemická syntéza $x farmakologie $7 D011685
- 650 _2
- $a vztahy mezi strukturou a aktivitou $7 D013329
- 655 _2
- $a časopisecké články $7 D016428
- 655 _2
- $a práce podpořená grantem $7 D013485
- 700 1_
- $a Caletková, Olga $u Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nam. 2, CZ-16610 Prague 6, Czech Republic.
- 700 1_
- $a Perlíková, Pavla $u Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nam. 2, CZ-16610 Prague 6, Czech Republic.
- 700 1_
- $a Poštová Slavětínská, Lenka $u Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nam. 2, CZ-16610 Prague 6, Czech Republic.
- 700 1_
- $a Tloušťová, Eva $u Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nam. 2, CZ-16610 Prague 6, Czech Republic.
- 700 1_
- $a Hodek, Jan $u Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nam. 2, CZ-16610 Prague 6, Czech Republic.
- 700 1_
- $a Weber, Jan $u Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nam. 2, CZ-16610 Prague 6, Czech Republic.
- 700 1_
- $a Džubák, Petr $u Institute of Molecular and Translational Medicine, Palacky University and University Hospital in Olomouc, Faculty of Medicine and Dentistry, Hněvotínská 5, 77515 Olomouc, Czech Republic.
- 700 1_
- $a Hajdúch, Marián $u Institute of Molecular and Translational Medicine, Palacky University and University Hospital in Olomouc, Faculty of Medicine and Dentistry, Hněvotínská 5, 77515 Olomouc, Czech Republic.
- 700 1_
- $a Hocek, Michal $u Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nam. 2, CZ-16610 Prague 6, Czech Republic; Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, CZ-12843 Prague 2, Czech Republic. Electronic address: hocek@uochb.cas.cz.
- 773 0_
- $w MED00000769 $t Bioorganic & medicinal chemistry $x 1464-3391 $g Roč. 23, č. 23 (2015), s. 7422-38
- 856 41
- $u https://pubmed.ncbi.nlm.nih.gov/26558518 $y Pubmed
- 910 __
- $a ABA008 $b sig $c sign $y a $z 0
- 990 __
- $a 20161005 $b ABA008
- 991 __
- $a 20161021095929 $b ABA008
- 999 __
- $a ok $b bmc $g 1166284 $s 952600
- BAS __
- $a 3
- BAS __
- $a PreBMC
- BMC __
- $a 2015 $b 23 $c 23 $d 7422-38 $e 20151031 $i 1464-3391 $m Bioorganic & medicinal chemistry $n Bioorg Med Chem $x MED00000769
- LZP __
- $a Pubmed-20161005