Fluorinated pyrrolo[2,3-d]pyrimidine nucleosides: 7-fluoro-7-deazapurine 2 `-deoxyribofuranosides and 2 `-deoxy-2 `-fluoroarabinofuranosyl derivatives
DC Element | Wert | Sprache |
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dc.contributor.author | Seela, Frank | |
dc.contributor.author | Xu, Kuiying | |
dc.contributor.author | Chittepu, Padmaja | |
dc.date.accessioned | 2021-12-23T16:06:26Z | - |
dc.date.available | 2021-12-23T16:06:26Z | - |
dc.date.issued | 2006 | |
dc.identifier.issn | 00397881 | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/7401 | - |
dc.description.abstract | The syntheses of 7-deaza-7-fluoro-2'-deoxyadenosine (1a), 7-deaza-7-fluoro-2'-deoxyinosine (3a) and 7-deaza-7-fluoro-2'-deoxyguanosine (3c) as well as of the 2'-deoxy-2'-fluoroarabino-furanosyl derivatives 1b, 3b are described. Starting materials were 6-chloro-7-fluoro-7-deazapurine (4-chloro-5-fluoropyrrolo[2.3-d]pyrimidine, 4b) and 2-pivaloylamino-6-chloro-7-fluoro-7-deazapurine (2-pivaloylaniino-4-chloro-5-fluoropyrrolo[2.3-d]pyrimidine, 6). Nucleobase anion glycosylation of 4b or 6 with the halogenoses 7 or 9 furnished the protected beta-D-nucleosides 8. 10 and 11, which were converted to compounds 1a, 1b by ammonolysis and to 2a-c by sodium methoxide treatment. The 2'-deoxymosine derivatives 3a, 3b and the guanosine analogue 3c were obtained from 2a-c. Conformational analysis of the nucleosides 1a, 1b was performed in solution and in the solid state. Single-crystal X-ray analyses showed that the sugar moiety of 1a exhibits the S-conformation (P = 164.8 degrees, tau = 40.1 degrees). In solution the 2'-fluoro sub-stituents shift the sugar conformation slightly towards N. | |
dc.language.iso | en | |
dc.publisher | GEORG THIEME VERLAG KG | |
dc.relation.ispartof | SYNTHESIS-STUTTGART | |
dc.subject | 2'-DEOXY-2'-FLUORO-BETA-D-ARABINONUCLEOSIDES | |
dc.subject | 7-DEAZAPURINE NUCLEOSIDES | |
dc.subject | ANALOGS | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Organic | |
dc.subject | CONFORMATION | |
dc.subject | DNA | |
dc.subject | fluorine | |
dc.subject | glycosylations | |
dc.subject | HALOGENATION | |
dc.subject | IN-VITRO | |
dc.subject | INHIBITOR | |
dc.subject | nucleosides | |
dc.subject | OLIGONUCLEOTIDES | |
dc.subject | pyrrolo[2,3-d]pyrimidines | |
dc.subject | STABILITY | |
dc.subject | sugar conformation | |
dc.title | Fluorinated pyrrolo[2,3-d]pyrimidine nucleosides: 7-fluoro-7-deazapurine 2 `-deoxyribofuranosides and 2 `-deoxy-2 `-fluoroarabinofuranosyl derivatives | |
dc.type | journal article | |
dc.identifier.doi | 10.1055/s-2006-942400 | |
dc.identifier.isi | ISI:000238841100016 | |
dc.description.issue | 12 | |
dc.description.startpage | 2005 | |
dc.description.endpage | 2012 | |
dc.publisher.place | RUDIGERSTR 14, D-70469 STUTTGART, GERMANY | |
dcterms.isPartOf.abbreviation | Synthesis |
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geprüft am 01.06.2024