Hrvatska znanstvena bibliografija (CROSBI)



Pregled bibliografske jedinice broj: 260422

Časopis

Autori: Krištafor, Vedran; Raić-Malić, Silvana; Cetina, Mario; Kralj, Marijeta; Šuman, Lidija; Pavelić, Krešimir; Balzarini, Jan; De Clercq, Erik; Mintas, Mladen
Naslov: Synthesis, X-ray Crystal Structural Study, Antiviral and Cytostatic Evaluations of the Novel Unsaturated Acyclic and Epoxide Nucleoside Analogues
( Synthesis, X-ray Crystal Structural Study, Antiviral and Cytostatic Evaluations of the Novel Unsaturated Acyclic and Epoxide Nucleoside Analogues )
Izvornik: Bioorganic and Medicinal Chemistry (0968-0896) 14 (2006), 23; 8126-8138
Vrsta rada: članak
Ključne riječi: olephinic nucleoside analogues; epoxide purine derivatives; cytostytic activity; anti-HIV-1 activity
( olephinic nucleoside analogues; epoxide purine derivatives; cytostytic activity; anti-HIV-1 activity )
Sažetak:
A series of the novel purine and pyrimidine nucleoside analogues were synthesised in which the sugar moiety was replaced by the 4-amino-2-butenyl (2-6 and 10-18) and oxiranyl (8 and 20) spacer. Novel Z- (2-6) and E-isomers (10-18) of unsaturated acyclic nucleoside analogues were synthesized by condensation of 2- and 6-substituted purine and 5-substituted uracil bases with Z- (1) or E-phthalimide (9) precursors. The oxiranyl nucleoside analogues (8 and 20) were obtained by epoxidation of 1 and 9 with m-chloroperoxybenzoic acid and subsequent coupling with adenine. All the novel compounds were evaluated for their antiviral and antitumor cell activities. Among the olefinic nucleoside analogues, Z-isomer of adenine containing 4-amino-2-butenyl side chain (6) exhibited the best cytostatic activities, particularly against colon carcinoma (SW 620, IC50 = 26 uM). Its E-isomer 15 did not show any antiprolipherative activity against malignant tumor cell lines, except for a slight inhibition of colon carcinoma (SW 620, IC50 = 56.5 uM) cells. In general, Z-isomers showed better cytostatic activities than the corresponding E-isomers. (Z)-4-Amino-2-butenyl-adenine nucleoside analogue 6 showed albeit modest but selective activity against HIV-1 (EC50 = 4.83 ugmL-1).
Projekt / tema: 0098093, 0125003
Izvorni jezik: eng
Rad je indeksiran u
bazama podataka:
Current Contents Connect (CCC)
MEDLINE
Scopus
SCI-EXP, SSCI i/ili A&HCI
Science Citation Index Expanded (SCI-EXP) (sastavni dio Web of Science Core Collectiona)
Kategorija: Znanstveni
Znanstvena područja:
Kemija,Temeljne medicinske znanosti
URL cjelovitog teksta:
Google Scholar: Synthesis, X-ray Crystal Structural Study, Antiviral and Cytostatic Evaluations of the Novel Unsaturated Acyclic and Epoxide Nucleoside Analogues