Fluorinated pyrrolo[2,3-d]pyrimidine nucleosides: 7-fluoro-7-deazapurine 2 `-deoxyribofuranosides and 2 `-deoxy-2 `-fluoroarabinofuranosyl derivatives

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dc.contributor.authorSeela, Frank
dc.contributor.authorXu, Kuiying
dc.contributor.authorChittepu, Padmaja
dc.date.accessioned2021-12-23T16:06:26Z-
dc.date.available2021-12-23T16:06:26Z-
dc.date.issued2006
dc.identifier.issn00397881
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/7401-
dc.description.abstractThe 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.isoen
dc.publisherGEORG THIEME VERLAG KG
dc.relation.ispartofSYNTHESIS-STUTTGART
dc.subject2'-DEOXY-2'-FLUORO-BETA-D-ARABINONUCLEOSIDES
dc.subject7-DEAZAPURINE NUCLEOSIDES
dc.subjectANALOGS
dc.subjectChemistry
dc.subjectChemistry, Organic
dc.subjectCONFORMATION
dc.subjectDNA
dc.subjectfluorine
dc.subjectglycosylations
dc.subjectHALOGENATION
dc.subjectIN-VITRO
dc.subjectINHIBITOR
dc.subjectnucleosides
dc.subjectOLIGONUCLEOTIDES
dc.subjectpyrrolo[2,3-d]pyrimidines
dc.subjectSTABILITY
dc.subjectsugar conformation
dc.titleFluorinated pyrrolo[2,3-d]pyrimidine nucleosides: 7-fluoro-7-deazapurine 2 `-deoxyribofuranosides and 2 `-deoxy-2 `-fluoroarabinofuranosyl derivatives
dc.typejournal article
dc.identifier.doi10.1055/s-2006-942400
dc.identifier.isiISI:000238841100016
dc.description.issue12
dc.description.startpage2005
dc.description.endpage2012
dc.publisher.placeRUDIGERSTR 14, D-70469 STUTTGART, GERMANY
dcterms.isPartOf.abbreviationSynthesis
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