Naslov
Antiviral and cytostatic evaluation of the novel 6-acyclic chain substituted thymine derivatives

Autori
Prekupec, Svjetlana ; Makuc, Damjan ; Plavec, Janez ; Kraljević, Sandra ; Kralj, Marijeta ; Pavelić, Krešimir ; Andrei, Graciela ; Snoeck, Robert ; Balzarini, Jan ; De Clercq, Erik ; Raić-Malić, Silvana ; Mintas, Mladen

Izvornik
Antiviral chemistry & chemotherapy (0956-3202) 16 (2005), 5; 327-338

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
C-6 fluoroalkylated pyrimidine derivatives ; conformational analysis ; antiviral activity ; cytostatic activity ; apoptosis

Sažetak
A series of the novel 5-methyl pyrimidine derivatives with an acyclic side chain at the C-6 position were synthesized using lithiation of a 2, 4-dimethoxy-5, 6-dimethyl pyrimidine and subsequent nucleophilic addition or substitution reactions of the organolithium intermediate thus obtained with acetaldehyde, epichlorhydrine, fluorinated ketones and fluorinated ester. The novel compounds were evaluated on their cytostatic and antiviral activities. Among all the compounds evaluated, two fluorinated acyclic pyrimidine derivatives showed the highest cytostatic activities. The compound containing a 2-hydroxy-3, 3, 3-trifluoro-1-propenyl side chain exhibited a pronounced effect against breast carcinoma (MCF-7, IC50 = 8.38 ug/ml), while the compound with 1 2-fluoromethyl-2-acetoxypropyl chain exhibited moderate effect against cervical carcinoma (HeLa, IC50 = 19.73 ug/ml).

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija, Temeljne medicinske znanosti

POVEZANOST RADA