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Titolo:
Enantiomeric synthesis of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus
Autore:
Song, GY; Paul, V; Choo, H; Morrey, J; Sidwell, RW; Schinazi, RF; Chu, CK;
Indirizzi:
Univ Georgia, Coll Pharm, Athens, GA 30602 USA Univ Georgia Athens GA USA30602 eorgia, Coll Pharm, Athens, GA 30602 USA Utah State Univ, Inst Antiviral Res, Logan, UT 84322 USA Utah State Univ Logan UT USA 84322 nst Antiviral Res, Logan, UT 84322 USA Emory Univ, Sch Med, Decatur, GA 30033 USA Emory Univ Decatur GA USA 30033 mory Univ, Sch Med, Decatur, GA 30033 USA Vet Affairs Med Ctr, Decatur, GA 30033 USA Vet Affairs Med Ctr Decatur GAUSA 30033 s Med Ctr, Decatur, GA 30033 USA
Titolo Testata:
JOURNAL OF MEDICINAL CHEMISTRY
fascicolo: 23, volume: 44, anno: 2001,
pagine: 3985 - 3993
SICI:
0022-2623(20011108)44:23<3985:ESODAL>2.0.ZU;2-Q
Fonte:
ISI
Lingua:
ENG
Soggetto:
S-ADENOSYLHOMOCYSTEINE HYDROLASE; HUMAN-IMMUNODEFICIENCY-VIRUS; CARBOCYCLIC NUCLEOSIDES; ENANTIOSELECTIVE SYNTHESIS; NEPLANOCIN-A; ANTI-HIV; ANALOGS; (-)-NEPLANOCIN-A; REPLICATION; INHIBITION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
43
Recensione:
Indirizzi per estratti:
Indirizzo: Chu, CK Univ Georgia, Coll Pharm, Athens, GA 30602 USA Univ Georgia Athens GA USA 30602 Coll Pharm, Athens, GA 30602 USA
Citazione:
G.Y. Song et al., "Enantiomeric synthesis of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus", J MED CHEM, 44(23), 2001, pp. 3985-3993

Abstract

Enantiomeric synthesis Of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus are described. The key intermediate (-)- and (+)-cyclopentenyl alcohols (7 and 15) were prepared from D-gamma -ribonolactone and D-ribose, respectively. Coupling of 7 with appropriately blocked purine and pyrimidine bases via the Mitsunobu reaction followed by deprotection afforded the target L-(+)-cyclopentenyl nucleosides (24-28, 31, 33, and 36). D-(-)Cyclopentenyl nucleosides (1, 40, 43, and 52-56) were also prepared by a similar procedure for L-isomers from 15. The synthesized compounds were evaluated for their antiviral activity against two RNA viruses: HIV and West Nile virus. Among the synthesized D-(-)-nucleosides, adenine (1, neplanocin A), cytosine (55, CPE-C), and 5-fluorocytosine (56) analogues exhibited moderate to potent anti-HIV activity (EC50 0.1, 0.06, and 5.34 muM, respectively) with significant cytotoxicity in PBM, Vero, and CEM cells. Also, cytosine (55) and 5-fluorocytosine (56) analogues exhibited the most potent anti-West Nile virus activity (EC50 0.2-3.0 and 15-20muM, respectively). Among L-(+)-nucleosides, only the cytosine (27) analogue exhibited weak anti-HIV activity (EC50 58.9 muM).

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Documento generato il 15/07/20 alle ore 14:13:39