Synthesis of allopurinol and 4-amino-1H-pyrazolo[3,4-d]pyrimidine N1- and N2-(β-D-arabinofuranosides)

DC FieldValueLanguage
dc.contributor.authorSeela, F.
dc.contributor.authorWinter, H.
dc.date.accessioned2021-12-23T16:26:21Z-
dc.date.available2021-12-23T16:26:21Z-
dc.date.issued1991
dc.identifier.issn01702041
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/14939-
dc.description.abstractAllopurinol and 4-amino-1H-pyrazolo[3,4-d]pyrimidine N1-and N2-(D-arabinofuranosides) have been synthesized. Nucleobase anion glycosylation of 4-methoxy-1H-pyrazolo[3,4-d]-pyrimidine (7) with the α-D-arabinofuranosyl chloride 6a proceeds stereoselectively and affords the N1-(β-D-nucleoside) 8 as the main product (43% yield) together with the N2 isomer 10 (25% yield). The formation of the α anomer 9 (6% yield) results from the β-D-arabinofuranosyl chloride 6b being formed upon chlorination of the nitrobenzoate 5. Compounds were deprotected (11–13) and subjected to nucleophilic displacement reactions affording allopurinol and 8-aza-7-deazaadenine N1-and N2-(arabinonucleosides) 1b, 2b, 3, and 4b. The anomeric configuration and the position of glycosylation have been established by 1D 1H-NOE difference spectroscopy. Compound 3 has proved to be a substrate of adenosine deaminase with a half-life 100-fold longer than that of ara-A. Copyright © 1991 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
dc.language.isoen
dc.relation.ispartofLiebigs Annalen der Chemie
dc.subjectAdenosine deaminase
dc.subjectD-Arabinonucleosides
dc.subjectGlycosylation, nucleobase-anion
dc.subjectPhase-transfer catalysis
dc.subjectPyrazolo[3,4-d]pyrimidines
dc.titleSynthesis of allopurinol and 4-amino-1H-pyrazolo[3,4-d]pyrimidine N1- and N2-(β-D-arabinofuranosides)
dc.typejournal article
dc.identifier.doi10.1002/jlac.199119910120
dc.identifier.scopus2-s2.0-84986730886
dc.identifier.urlhttps://www.scopus.com/inward/record.uri?eid=2-s2.0-84986730886&doi=10.1002%2fjlac.199119910120&partnerID=40&md5=3aa6c4fe46a8ec5d5d3fabf4d5939615
dc.description.volume1991
dc.description.issue2
dc.description.startpage105
dc.description.endpage109
dcterms.isPartOf.abbreviationEur. J. Org. Chem.
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