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Titolo:
Syntheses of 4-[1-(2-deoxy-beta-D-ribofuranosyl)]-derivatives of 2-substituted-5-fluoroaniline: '' cytosine replacement '' analogs of deoxycytidine for evaluation as anticancer and antihuman immunodeficiency virus (anti-HIV)agents
Autore:
Wang, ZX; Wiebe, LI; De Clercq, E; Balzarini, J; Knaus, EE;
Indirizzi:
Univ Alberta, Fac Pharm & Pharmaceut Sci, Edmonton, AB T6G 2N8, Canada Univ Alberta Edmonton AB Canada T6G 2N8 Sci, Edmonton, AB T6G 2N8, Canada Rega Inst Med Res, B-3000 Louvain, Belgium Rega Inst Med Res Louvain Belgium B-3000 ed Res, B-3000 Louvain, Belgium
Titolo Testata:
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
fascicolo: 8, volume: 78, anno: 2000,
pagine: 1081 - 1088
SICI:
0008-4042(200008)78:8<1081:SO4O2>2.0.ZU;2-A
Fonte:
ISI
Lingua:
ENG
Soggetto:
C-NUCLEOSIDES; FURANOID GLYCALS; REPLICATION; DNA; DIFLUOROTOLUENE; GLYCOSIDES; INFECTION; ADENINE; FACILE;
Keywords:
fluoroanilines; deoxycytidine mimics; anticancer-antihuman immunodeficiency virus (HIV) evaluation;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
40
Recensione:
Indirizzi per estratti:
Indirizzo: Knaus, EE Univ Alberta, Fac Pharm & Pharmaceut Sci, Edmonton, AB T6G 2N8, Canada Univ Alberta Edmonton AB Canada T6G 2N8 ton, AB T6G 2N8, Canada
Citazione:
Z.X. Wang et al., "Syntheses of 4-[1-(2-deoxy-beta-D-ribofuranosyl)]-derivatives of 2-substituted-5-fluoroaniline: '' cytosine replacement '' analogs of deoxycytidine for evaluation as anticancer and antihuman immunodeficiency virus (anti-HIV)agents", CAN J CHEM, 78(8), 2000, pp. 1081-1088

Abstract

A group of 4-[1-(2-deoxy-beta-D-ribofuranosyl)]-derivatives of 5-fluoroaniline possessing a variety of aryl C-2 substituents (6a R = H, 6b R = F, 6c R = Me) were synthesized. Accordingly, a Heck-type coupling reaction of the4-iodoaniline derivatives (13a-c) with the bis(tert-butyldimethylsilyl)glycal (11) in the presence of Pd(OAc)(2) and Ph3As, followed by removal of the tert-butyldimethylsilyl protection groups using n-Bu4N+F-, yielded the corresponding 4-(beta-D-glycero-pentofuran-3-ulos-1-yl)aniline derivatives (14a-c) having a C-3 C=O in the sugar ring. Reduction of the C-3 C=O compounds (14a-c) using NaB(OAc)(3)H afforded the target 4-[1-(2-deoxy-beta-D-ribofuranosyl)]-derivatives of the respective 2-substituted-5-fluoroaniline (6a-c). The deoxycytidine mimic, 3-fluoro-4-[1-(2-deoxy-beta-D-ribofuranosyl)]aniline (6a), in which the cytosine ring of deoxycytidine is replaced by a 4-(3-fluoroaniline) ring system, was inactive as an anticancer agent againsta variety of tumor cell lines, and as an antihuman immunodeficiency virus (HIV-1, HIV-2) agent. The failure of this unnatural deoxycytidine mimic (6a) to exhibit anticancer-antiviral activity may be due to its inability to undergo phosphorylation by host cell- and virus-induced kinases.

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Documento generato il 02/04/20 alle ore 12:29:04