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Titolo:
RING-EXPANDED NUCLEOSIDE ANALOGS - 1,3-DIOXAN-5-YL PYRIMIDINES
Autore:
CADET G; CHAN CS; DANIEL RY; DAVIS CP; GUIADEEN D; RODRIGUEZ G; THOMAS T; WALCOTT S; SCHEINER P;
Indirizzi:
CUNY YORK COLL,DEPT NAT SCI JAMAICA NY 11451 CUNY YORK COLL,DEPT NAT SCI JAMAICA NY 11451
Titolo Testata:
Journal of organic chemistry
fascicolo: 14, volume: 63, anno: 1998,
pagine: 4574 - 4580
SICI:
0022-3263(1998)63:14<4574:RNA-1P>2.0.ZU;2-3
Fonte:
ISI
Lingua:
ENG
Soggetto:
HUMAN IMMUNODEFICIENCY VIRUSES; CONFORMATIONAL-ANALYSIS; 1,5-ANHYDROHEXITOL NUCLEOSIDES; CYCLOHEXENYL NUCLEOSIDES; ASYMMETRIC-SYNTHESIS; ANTIVIRAL ACTIVITIES; HIV; -1-)3-HYDROXY-2-(PHOSPHONYLMETHOXY)PROPYL>CYTOSINE; DERIVATIVES; ENANTIOMERS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
55
Recensione:
Indirizzi per estratti:
Citazione:
G. Cadet et al., "RING-EXPANDED NUCLEOSIDE ANALOGS - 1,3-DIOXAN-5-YL PYRIMIDINES", Journal of organic chemistry, 63(14), 1998, pp. 4574-4580

Abstract

1,3-Dioxan-5-yl pyrimidine nucleoside analogues, higher homologues ofantiviral and anticancer 1,3-dioxolanes, were prepared from bis-1,3-tritylglycerol and 3-benzoylated bases (uracil, 5-fluorouracil, thymine). Mitsunobu condensation, deprotection, and cycloacetalization gave cis/trans mixtures of 2,5-disubstituted-1,3-dioxanes in which the desired cis stereoisomers predominated. Cytosine derivatives could not be obtained in this manner; N-4-benzoylcytosine afforded an O-2 alkylated Mitsunobu product that rearranged to an O-2-(2,3-dihydroxypropyl)cytosine on detritylation with aqueous acetic acid. Cytosine and 5-fluorocytosine nucleosides were therefore prepared from the corresponding uracils via their 1,2,4-triazole derivatives. H-1 NMR data established theconformational preference for equatorial 2'-hydroxymethyl and axial 5'-base in the cis isomers; the trans compounds were diequatorial. Despite their conformations, the cis nucleosides showed no antiviral activity.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 19/09/20 alle ore 09:15:20