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Synthesis, Cytostatic and Antiviral Evaluations of the New C-5 Substituted Pyrimidine and Furo[2, 3-d]pyrimidine 4, 5-Didehydro-L-ascorbic Acid Derivatives


Gazivoda, Tatjana; Šokčević, Mario; Kralj, Marijeta; Šuman, Lidija; Pavelić, Krešimir; De Clercq, Erik; Andrei, Graciela; Snoeck, Robert; Balzarini, Jan; Mintas, Mladen; Raić-Malić, Silvana
Synthesis, Cytostatic and Antiviral Evaluations of the New C-5 Substituted Pyrimidine and Furo[2, 3-d]pyrimidine 4, 5-Didehydro-L-ascorbic Acid Derivatives // III Simposio Internacional de Quimica : sumarios = III International Symposium On Chemistry : abstracts ; AP45 / P. Garciga, P. (ur.).
Santa Clara City: Facultad de Química y Farmacia, Universidad Central, 2007. (poster, međunarodna recenzija, sažetak, znanstveni)


Naslov
Synthesis, Cytostatic and Antiviral Evaluations of the New C-5 Substituted Pyrimidine and Furo[2, 3-d]pyrimidine 4, 5-Didehydro-L-ascorbic Acid Derivatives

Autori
Gazivoda, Tatjana ; Šokčević, Mario ; Kralj, Marijeta ; Šuman, Lidija ; Pavelić, Krešimir ; De Clercq, Erik ; Andrei, Graciela ; Snoeck, Robert ; Balzarini, Jan ; Mintas, Mladen ; Raić-Malić, Silvana

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
III Simposio Internacional de Quimica : sumarios = III International Symposium On Chemistry : abstracts ; AP45 / P. Garciga, P. - Santa Clara City : Facultad de Química y Farmacia, Universidad Central, 2007

Skup
International Symposium On Chemistry (3 ; 2007)

Mjesto i datum
Santa Clara City, Kuba, 05.-08.06.2007

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
C-5 substituted pyrimidine and furo[2; 3-d]pyrimidine derivatives; L-ascorbic acid; cytostatic evaluations

Sažetak
Some pyrimidine and purine derivatives of 4, 5-didehydro-5, 6-dideoxy-L-ascorbic acid exerted pronounced cytostatic and antiviral activities.1 The novel C-5 alkynyl substituted pyrimidine (1-11) and furo[2, 3-d]pyrimidine derivatives (12-22) of L-ascorbic acid (Figure) were synthesized by coupling of 5-iodouracil-4, 5-didehydro-5, 6-dideoxy-L-ascorbic acid with terminal alkynes by using Sonogashira cross-coupling reaction conditions. The new compounds were evaluated for their cytostatic and antiviral activities. Among all evaluated compounds the octynyl-substituted uracil derivative of L-ascorbic acid (3) exhibited the most pronounced cytostatic activities against all examined tumor cell lines (IC50: 2-12 μ M). Pyrimidine derivatives of L-ascorbic acid containing p-substituted phenylacetylene groups (8-11) displayed also a rather pronounced (IC50: 3-37 μ M) inhibitory effect towards all tumor cell lines. From the bicyclic series of compounds, 6-butylfuro[2, 3-d]pyrimidine derivative (12) and 6-p-bromophenylfuro[2, 3-d]pyrimidine derivative (19) showed the highest cytostatic activity (IC50: 4.5-20 μ M), particularly against malignant leukemia (L1210) and T-lymphocyte (Molt4/C8 and CEM) cells. Compounds 8 and 9 also showed some activity against cytomegalovirus (CMV, Davis strain, EC50: 1.5 μ M) at a 10-fold lower concentration than that required for cytotoxicity. Thus, the compounds reported here are worth considering for further development as potential leads for cytostatic and/or antiviral agents. 1. Raić-Malić, S. et al, J. Med. Chem. 1999 (42) 2673 ; Raić-Malić, S. et al. J. Med. Chem. 2000 (43) 4806 ; Gazivoda, T. et al, Bioorg. Med. Chem., 2005 (13) 131 ; Gazivoda, T. et al. Bioorg. Med. Chem. 2007 (15) 749.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekt / tema
098-0982464-2393 - Molekularna obilježja miofibroblasta Dupuytrenove bolesti (Krešimir Pavelić, )
098-0982464-2514 - Uloga različitih mehanizama odgovora stanica na terapiju oštećenjem DNA (Marijeta Kralj, )
125-0982464-2922 - RAZVOJ NOVIH PROLIJEKOVA I LIJEKOVA PROTIV VIRUSA I RAKA (Mladen Mintas, )
125-0982464-2925 - Razvoj i primjena novih molekula u pozitron-emisijskoj tomografiji (PET) (Silvana Raić-Malić, )

Ustanove
Institut "Ruđer Bošković", Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb