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Novel C-6 Fluorinated Acyclic Side Chain Pyrimidine Derivatives: Synthesis, 1H and 13C NMR Conformational Studies, Antiviral and Cytostatic Evaluations (CROSBI ID 533839)

Prilog sa skupa u zborniku | sažetak izlaganja sa skupa | međunarodna recenzija

Prekupec, Svjetlana ; Makuc, Damjan ; Plavec, Janez ; Šuman, Lidija ; Kralj, Marijeta ; Pavelić, Krešimir ; Balzarini, Jan ; De Clercq, Erik ; Mintas, Mladen ; Raić-Malić, Silvana Novel C-6 Fluorinated Acyclic Side Chain Pyrimidine Derivatives: Synthesis, 1H and 13C NMR Conformational Studies, Antiviral and Cytostatic Evaluations // III Simposio Internacional de Quimica / P. Garciga (ur.). Santa Clara (CA): Facultad de Química y Farmacia, Universidad Central, 2007. str. AP44-x

Podaci o odgovornosti

Prekupec, Svjetlana ; Makuc, Damjan ; Plavec, Janez ; Šuman, Lidija ; Kralj, Marijeta ; Pavelić, Krešimir ; Balzarini, Jan ; De Clercq, Erik ; Mintas, Mladen ; Raić-Malić, Silvana

engleski

Novel C-6 Fluorinated Acyclic Side Chain Pyrimidine Derivatives: Synthesis, 1H and 13C NMR Conformational Studies, Antiviral and Cytostatic Evaluations

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.

C-6 fluorinated pyrimidine derivatives; 1H and 13C NMR conformational studies; antiviral and aytostatic evaluations

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Podaci o prilogu

AP44-x.

2007.

objavljeno

Podaci o matičnoj publikaciji

III Simposio Internacional de Quimica

P. Garciga

Santa Clara (CA): Facultad de Química y Farmacia, Universidad Central

Podaci o skupu

III International Symposium On Chemistry

poster

05.06.2007-08.06.2007

Santa Clara, Kuba

Povezanost rada

Kemija, Temeljne medicinske znanosti