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Autori: Prekupec, Svjetlana; Makuc, Damjan; Plavec, Janez; Šuman, Lidija; Kralj, Marijeta; Pavelić, Krešimir; Balzarini, Jan; De Clercq, Erik; Mintas, Mladen; Raić-Malić, Silvana
Naslov: Novel C-6 Fluorinated Acyclic Side Chain Pyrimidine Derivatives: Synthesis, 1H and 13C NMR Conformational Studies, Antiviral and Cytostatic Evaluations
Izvornik: III Simposio Internacional de Quimica / P. Garciga (ur.). - Santa Clara City : Facultad de Química y Farmacia, Universidad Central , 2007. AP44.
Skup: III International Symposium On Chemistry
Mjesto i datum: Santa Clara City, Cuba, 05-08.06.2007.
Ključne riječi: C-6 fluorinated pyrimidine derivatives; 1H and 13C NMR conformational studies; antiviral and aytostatic evaluations
Sažetak:
The synthetic route for introduction of a fluoroalkyl (7-12, 14), fluoroalkenyl (16 and 17), fluorophenylalkyl (18, 20, 21 and 23) and fluorophenylalkenyl (19, 22) side chain at C-6 of the pyrimidine involved the lithiation of the pyrimidine derivatives 3 and 3a and subsequent nucleophilic addition or substitution reactions of the organolithium intermediate thus obtained with various electrophiles (Figure).1 Conformational properties of the novel fluorinated pyrimidine derivatives were assessed by the use of 1D difference NOE enhancements and C-F coupling constants. The novel compounds were evaluated for their antiviral and cytostatic activities. Of all compounds evaluated, the 5-bromopyrimidine derivatives 5 and 6 showed the highest inhibitory activities. Among the series of fluoroalkylated pyrimidines that is generally more active than the series of fluorophenylalkylated pyrimidines, compounds 8 and 14 displayed moderate cytostatic activities against the tested tumor cell lines. Compounds 6, 8 and 15a are worth considering for further development because they afforded a limited specific activity against varicella zoster virus (VZV) and cytomegalovirus (CMV) at a  10-fold lower concentration than that required for cytotoxicity. 1. Raić-Malić, S., et al., Nucl. Nucl. & Nucl. Acids 2004, 23, 1707 ; Johayem, A., Raić-Malić, S., et al., Chemistry&Biodiversity 2006, 3, 274 ; Prekupec, S., Raić-Malić, S., et al., Antiviral Chem. & Chemother. 2005, 16, 327.
Vrsta sudjelovanja: Poster
Vrsta prezentacije u zborniku: Sažetak
Vrsta recenzije: Međunarodna recenzija
Projekt / tema: 125-0982464-2925, 125-0982464-2922, 098-0982464-2393, 098-0982464-2514
Izvorni jezik: ENG
Kategorija: Znanstveni
Znanstvena područja:
Kemija,Temeljne medicinske znanosti
Upisao u CROSBI: Silvana Raić Malić (sraic@pierre.fkit.hr), 25. Ožu. 2008. u 14:59 sati



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