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Pregled bibliografske jedinice broj: 326146

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 & medicinal chemistry, 16 (2008), 10; 5624-5634 doi:10.1016/j.bmc.2008.03.074 (međunarodna recenzija, članak, znanstveni)

CROSBI ID: 326146 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

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 & 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

Projekti:
MZOS-125-0982464-2922 - RAZVOJ NOVIH PROLIJEKOVA I LIJEKOVA PROTIV VIRUSA I RAKA (Mintas, Mladen, MZOS ) ( CroRIS)
MZOS-125-0982464-2925 - Razvoj i primjena novih molekula u pozitron-emisijskoj tomografiji (PET) (Raić-Malić, Silvana, MZOS ) ( CroRIS)
MZOS-335-0982464-2393 - Molekularna obilježja miofibroblasta Dupuytrenove bolesti (Pavelić, Krešimir, MZOS ) ( CroRIS)

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

Profili:

Avatar Url Tatjana Gazivoda Kraljević (autor)

Avatar Url Krešimir Pavelić (autor)

Avatar Url Mladen Mintas (autor)

Avatar Url Sandra Kraljević Pavelić (autor)

Avatar Url Vedran Krištafor (autor)

Avatar Url Siniša Bratulić (autor)

Avatar Url Silvana Raić-Malić (autor)

Poveznice na cjeloviti tekst rada:

doi www.sciencedirect.com doi.org

Citiraj ovu publikaciju:

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 & medicinal chemistry, 16 (2008), 10; 5624-5634 doi:10.1016/j.bmc.2008.03.074 (međunarodna recenzija, članak, znanstveni)
Gazivoda, T., Raić-Malić, S., Krištafor, V., Makuc, D., Plavec, J., Bratulić, S., Kraljević Pavelić, S., Pavelić, K., Naesens, L. & Andrei, G. (2008) Synthesis, cytostatic and anti-HIV evaluations of the new unsaturated acyclic C-5 pyrimidine nucleoside analogues. Bioorganic & medicinal chemistry, 16 (10), 5624-5634 doi:10.1016/j.bmc.2008.03.074.
@article{article, author = {Gazivoda, Tatjana and Rai\'{c}-Mali\'{c}, Silvana and Kri\v{s}tafor, Vedran and Makuc, Damjan and Plavec, Janez and Bratuli\'{c}, Sini\v{s}a and Kraljevi\'{c} Paveli\'{c}, Sandra and Paveli\'{c}, Kre\v{s}imir and Naesens, Lieve and Andrei, Graciela and Snoeck, Robert and Balzarini, Jan and Mintas, Mladen}, year = {2008}, pages = {5624-5634}, DOI = {10.1016/j.bmc.2008.03.074}, keywords = {unsaturated acyclic pyrimidine nucleoside analogues, Z- and E-isomers, cytostatic evaluations, anti-HIV activity}, journal = {Bioorganic and medicinal chemistry}, doi = {10.1016/j.bmc.2008.03.074}, volume = {16}, number = {10}, issn = {0968-0896}, title = {Synthesis, cytostatic and anti-HIV evaluations of the new unsaturated acyclic C-5 pyrimidine nucleoside analogues}, keyword = {unsaturated acyclic pyrimidine nucleoside analogues, Z- and E-isomers, cytostatic evaluations, anti-HIV activity} }
@article{article, author = {Gazivoda, Tatjana and Rai\'{c}-Mali\'{c}, Silvana and Kri\v{s}tafor, Vedran and Makuc, Damjan and Plavec, Janez and Bratuli\'{c}, Sini\v{s}a and Kraljevi\'{c} Paveli\'{c}, Sandra and Paveli\'{c}, Kre\v{s}imir and Naesens, Lieve and Andrei, Graciela and Snoeck, Robert and Balzarini, Jan and Mintas, Mladen}, year = {2008}, pages = {5624-5634}, DOI = {10.1016/j.bmc.2008.03.074}, keywords = {unsaturated acyclic pyrimidine nucleoside analogues, Z- and E-isomers, cytostatic evaluations, anti-HIV activity}, journal = {Bioorganic and medicinal chemistry}, doi = {10.1016/j.bmc.2008.03.074}, volume = {16}, number = {10}, issn = {0968-0896}, title = {Synthesis, cytostatic and anti-HIV evaluations of the new unsaturated acyclic C-5 pyrimidine nucleoside analogues}, keyword = {unsaturated acyclic pyrimidine nucleoside analogues, Z- and E-isomers, cytostatic evaluations, anti-HIV activity} }

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

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