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Pyrrolo[2,3-d]pyrimidine (7-deazapurine) as a privileged scaffold in design of antitumor and antiviral nucleosides
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SYSNO ASEP 0480866 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Pyrrolo[2,3-d]pyrimidine (7-deazapurine) as a privileged scaffold in design of antitumor and antiviral nucleosides Tvůrce(i) Perlíková, Pavla (UOCHB-X) RID, ORCID
Hocek, Michal (UOCHB-X) RID, ORCIDZdroj.dok. Medicinal Research Reviews. - : Wiley - ISSN 0198-6325
Roč. 37, č. 6 (2017), s. 1429-1460Poč.str. 32 s. Jazyk dok. eng - angličtina Země vyd. US - Spojené státy americké Klíč. slova antivirals ; cytostatics ; deazapurines ; nucleosides ; nucleotides Vědní obor RIV CC - Organická chemie Obor OECD Organic chemistry CEP GA16-00178S GA ČR - Grantová agentura ČR Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 000412672200007 EID SCOPUS 85027982788 DOI 10.1002/med.21465 Anotace 7-Deazapurine (pyrrolo[2,3-d]pyrimidine) nucleosides are important analogues of biogenic purine nucleosides with diverse biological activities. Replacement of the N7 atom with a carbon atom makes the five-membered ring more electron rich and brings a possibility of attaching additional substituents at the C7 position. This often leads to derivatives with increased base-pairing in DNA or RNA or better binding to enzymes. Several types of 7-deazapurine nucleosides with potent cytostatic or cytotoxic effects have been identified. The most promising are 7-hetaryl-7-deazaadenosines, which are activated in cancer cells by phosphorylation and get incorporated both to RNA (causing inhibition of proteosynthesis) and to DNA (causing DNA damage). Mechanism of action of other types of cytostatic nucleosides, 6-hetaryl-7-deazapurine and thieno-fused deazapurine ribonucleosides, is not yet known. Many 7-deazaadenosine derivatives are potent inhibitors of adenosine kinases. Many types of sugar-modified derivatives of 7-deazapurine nucleosides are also strong antivirals. Most important are 2'-C-methylribo- or 2'-C-methyl-2'-fluororibonucleosides with anti-HCV activities (several compounds underwent clinical trials). Some underexplored areas of potential interest are also outlined. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Rok sběru 2018 Elektronická adresa http://onlinelibrary.wiley.com/doi/10.1002/med.21465/full
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