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Synthesis, Cytostatic and Anti-HIV Evaluations of the New Unsaturated Acyclic C-5 Pyrimidine Nucleoside Analogues


Gazivoda, Tatjana; Raić-Malić, Silvana; Krištafor, Vedran; Makuc, Damjan; Plavec, Janez; Bratulić, Siniša; Kraljević Pavelić, Sandra; Pavelić, Krešimir; Naesens, Lieve; Andrei, Graciela et al.
Synthesis, Cytostatic and Anti-HIV Evaluations of the New Unsaturated Acyclic C-5 Pyrimidine Nucleoside Analogues // Bioorganic and Medicinal Chemistry, 16 (2008), 10; 5624-5634 (međunarodna recenzija, članak, znanstveni)


Naslov
Synthesis, Cytostatic and Anti-HIV Evaluations of the New Unsaturated Acyclic C-5 Pyrimidine Nucleoside Analogues

Autori
Gazivoda, Tatjana ; Raić-Malić, Silvana ; Krištafor, Vedran ; Makuc, Damjan ; Plavec, Janez ; Bratulić, Siniša ; Kraljević Pavelić, Sandra ; Pavelić, Krešimir ; Naesens, Lieve ; Andrei, Graciela ; Snoeck, Robert ; Balzarini, Jan ; Mintas, Mladen

Izvornik
Bioorganic and Medicinal Chemistry (0968-0896) 16 (2008), 10; 5624-5634

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

Ključne riječi
Unsaturated acyclic pyrimidine nucleoside analogues; Z- and E-isomers; cytostatic evaluations; anti-HIV activity

Sažetak
A series of the novel C-5 alkynyl pyrimidine nucleoside analogues (1-14) in which the sugar moiety was replaced by the conformationally restricted Z- and E-2-butenyl spacer between the phthalimido and pyrimidine ring were synthesized by using Sonogashira cross-coupling reaction. Cytostatic activity evaluation of the novel compounds showed that E-isomers exhibited, in general, better cytostatic activities than the corresponding Z-isomers. E-isomer 14 exhibited the best cytostatic effect against all evaluated malignant cell lines, particularly against hepatocellular carcinoma (Hep G2, IC50 = 4.3 uM). However, this compound was also cytotoxic to human normal fibroblasts (WI 38). Its Z- isomer 7 showed highly specific antiproliferative activity against Hep G2 (IC50 = 18 uM) and no cytotoxicity to WI 38. Moreover, compounds 3, 4 and 14 expressed some marginal inhibitory activity against HIV-1 and HIV-2.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekt / tema
098-0982464-2393 - Molekularna obilježja miofibroblasta Dupuytrenove bolesti (Krešimir Pavelić, )
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

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE