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Titolo:
Acyclic nucleoside/nucleotide analogues with an imidazole ring skeleton
Autore:
Chen, HM; Hosmane, RS;
Indirizzi:
Univ Maryland Baltimore Cty, Lab Drug Design & Synth, Dept Chem & Biochem,Baltimore, MD 21250 USA Univ Maryland Baltimore Cty Baltimore MD USA 21250altimore, MD 21250 USA
Titolo Testata:
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
fascicolo: 8, volume: 20, anno: 2001,
pagine: 1599 - 1614
SICI:
1525-7770(2001)20:8<1599:ANAWAI>2.0.ZU;2-G
Fonte:
ISI
Lingua:
ENG
Soggetto:
SIMPLEX VIRUS-INFECTIONS; NUCLEOTIDE ANALOGS; ANTIVIRAL AGENTS; HERPES-SIMPLEX; 9-(2-PHOSPHONYLMETHOXYETHYL)GUANINE PMEG; NUCLEOSIDE PHOSPHONATES; CELL-LINES; DERIVATIVES; THERAPY; PMEDAP;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
45
Recensione:
Indirizzi per estratti:
Indirizzo: Hosmane, RS Univ Maryland Baltimore Cty, Lab Drug Design & Synth, Dept Chem & Biochem,1000 Hilltop Circle, Baltimore, MD 21250 USA Univ Maryland Baltimore Cty 1000 Hilltop Circle Baltimore MD USA 21250
Citazione:
H.M. Chen e R.S. Hosmane, "Acyclic nucleoside/nucleotide analogues with an imidazole ring skeleton", NUCLEOS NUC, 20(8), 2001, pp. 1599-1614

Abstract

Syntheses of a few acyclic nucleoside and acyclic nucleoside phosphonate analogues containing an imidazole ring have been reported. These analogues include methyl 1-(2-hydroxyethoxymethyl)imidazole-4, 5-dicarbo-xylate (1), 4,5-dicarbamoyl-l-(2-hydroxyethoxymethyl)imidazole (2), 4,5-dicyano-1-(2-hydroxyethoxymethyl)imidazole (4), Methyl 1-(2-bromoethoxymethyl)imidazole-4,5-dicarboxylate (7), 4,5-dicyano(2-bromoethoxymethyl)imidazole (8), and Methyl 1-(2-phosphonomethoxyethyl)imidazole (10). Also reported are a few potential prodrugs of the above compounds, including the acetyl derivatives 5 and 6 (of I and 4, respectively), and the diethyl phosphonate ester 9 (of 10). In addition, the corresponding benzyl-protected precursors 11 and 12 (of 1 and 4, respectively), along with their common hydrolysis product, 1-(2-benzyloxy-ethoxymethyl)-4,5-imidazoledicarboxylic acid (3), are reported. Another potential prodrug included in the list is 1-(2-acetoxyethyl)-4,5-dicyanoimidazole (15). The compounds were screened for in vitro antiviral activity against a wide variety of herpes and respiratory viruses. The most active compound was the phosphonate analogue 9 which exhibited an anti-measles virus activity with an EC50 of < 2.5 mug/mL and an SI value of > 176.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 25/01/20 alle ore 06:25:10