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Titolo:
SYNTHESIS, STRUCTURE AND IN-VITRO ANTI-HUMAN-IMMUNODEFICIENCY-VIRUS ACTIVITY OF NOVEL 3-METHYL-1H,3H-THIAZOLO[3,4-A]BENZIMIDAZOLES
Autore:
CHIMIRRI A; GRASSO S; MONFORTE AM; MONFORTE P; RAO A; ZAPPALA M; BRUNO G; NICOLO F; PANNECOUQUE C; WITVROUW M; DECLERCQ E;
Indirizzi:
UNIV MESSINA,DIPARTIMENTO FARMACOCHIM,VIALE ANNUNZIATA I-98168 MESSINA ITALY UNIV MESSINA,DIPARTIMENTO FARMACOCHIM I-98168 MESSINA ITALY UNIV MESSINA,DIPARTIMENTO CHIM INORGAN CHIM ANALIT & CHIM FIS I-98166MESSINA ITALY CATHOLIC UNIV LOUVAIN,REGA INST MED RES B-3000 LOUVAIN BELGIUM
Titolo Testata:
Antiviral chemistry & chemotherapy
fascicolo: 5, volume: 9, anno: 1998,
pagine: 431 - 438
SICI:
0956-3202(1998)9:5<431:SSAIAA>2.0.ZU;2-R
Fonte:
ISI
Lingua:
ENG
Soggetto:
TRANSCRIPTASE INHIBITORS NNRTIS; HIV-1 REVERSE-TRANSCRIPTASE; AGENTS; INFECTIONS; 1H,3H-THIAZOLO)3,4-A>BENZIMIDAZOLES; STRATEGIES;
Keywords:
1H,3H-THIAZOLO[3,4-A]BENZIMIDAZOLES; X-RAY; ANTI-HIV ACTIVITY;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Science Citation Index Expanded
Science Citation Index Expanded
Citazioni:
23
Recensione:
Indirizzi per estratti:
Citazione:
A. Chimirri et al., "SYNTHESIS, STRUCTURE AND IN-VITRO ANTI-HUMAN-IMMUNODEFICIENCY-VIRUS ACTIVITY OF NOVEL 3-METHYL-1H,3H-THIAZOLO[3,4-A]BENZIMIDAZOLES", Antiviral chemistry & chemotherapy, 9(5), 1998, pp. 431-438

Abstract

A series of novel aryl-3-methyl-1H,3H-thiazolo[3,4-a]benzimidazoles, TBZ analogues, were synthesized and investigated as anti-human immunodeficiency virus (HIV) agents in order to study the effects of structural modifications on antiviral activity and cytotoxicity. They were proved to inhibit significantly HIV-1 replication in vitro without showing inhibitory activity on HIV-2 or simian immunodeficiency virus. Theirpotency was influenced by the presence of suitable substituents in the phenyl ring at C-1 as well as by their stereochemical characteristics. In fact, the most active compound of the series was the enyl)-3-methyl-1H,3H-thiazolo[3,4-a]benzimidazole, in which the butterfly-like conformation is stabilized by two intramolecular hydrogen bonds between the fluorine atoms and H-1 and H-3. This was made possible by the trans arrangement of C-1 and C-3 substituents, as shown by X-ray and NMR analysis.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 28/09/20 alle ore 14:46:38