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The unsaturated acyclic nucleoside analogues bearing a sterically constrained (Z)-4'-benzamido-2'-butenyl moiety : Synthesis, X-ray crystal structure study, cytostatic and antiviral activity evaluations


Benci, Krešimir; Wittine, Karlo; Radan, Malajka; Cetina, Mario; Sedić, Mirela; Kraljević Pavelić, Sandra; Pavelić, Krešimir; deClercq, Erik; Mintas, Mladen
The unsaturated acyclic nucleoside analogues bearing a sterically constrained (Z)-4'-benzamido-2'-butenyl moiety : Synthesis, X-ray crystal structure study, cytostatic and antiviral activity evaluations // Bioorganic & medicinal chemistry, 18 (2010), 17; 6249-6257 doi:10.1016/j.bmc.2010.07.035 (međunarodna recenzija, članak, znanstveni)


Naslov
The unsaturated acyclic nucleoside analogues bearing a sterically constrained (Z)-4'-benzamido-2'-butenyl moiety : Synthesis, X-ray crystal structure study, cytostatic and antiviral activity evaluations

Autori
Benci, Krešimir ; Wittine, Karlo ; Radan, Malajka ; Cetina, Mario ; Sedić, Mirela ; Kraljević Pavelić, Sandra ; Pavelić, Krešimir ; deClercq, Erik ; Mintas, Mladen

Izvornik
Bioorganic & medicinal chemistry (0968-0896) 18 (2010), 17; 6249-6257

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

Ključne riječi
Unsaturated acyclic nucleoside analogues; X-ray diffraction; supramolecular self-assembling; cytostatic activity; antiviral activity

Sažetak
A series of the novel acyclic unsaturated pyrimidine (1–12) and adenine (13) nucleoside analogues bearing conformationally restricted (Z)-2'-butenyl moiety were synthesized to evaluate their antiviral and cytostatic activity potency against malignant tumor cell lines and normal human fibroblast (WI38). The N-1 and/or N-3 acyclic side chain substitution in pyrimidine ring in N-3 substituted 5-trifluoromethyluracyl derivative (11), N-1, N-3 disubstituted 5-fluorouracyl derivative (12) and adenine derivative (13) was deduced from their 1H and 13C NMR spectra and confirmed by single crystal X-ray structure analysis. The X-ray crystal structure analysis 11-13 revealed also supramolecular self-assemblies that built infinite chains into two- and three–dimensional networks. The results of the in vitro cytostatic activity evaluations of 1-13 indicate that majority of the tested compounds exhibited a non-specific and moderate antiproliferative effect at the highest concentration (100 μM). Of all evaluated compounds on the tested cell lines only N-1-4'' fluoro-substituted-benzamide uracyl derivative (7) showed rather marked and selective inhibitory activity against the growth of MCF-7 cells at concentration of 2.7 µM and no cytotoxic effect on normal fibroblasts WI38. This compound can be therefore considered as potential lead compound for further synthetic structure modification.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekt / tema
119-1193079-3069 - Novi organski i koordinacijski spojevi - sinteza i suodnos struktura-svojstvo (Branko Kaitner, )
125-0982464-2922 - RAZVOJ NOVIH PROLIJEKOVA I LIJEKOVA PROTIV VIRUSA I RAKA (Mladen Mintas, )
335-0000000-3532 - Uloga IGF2 i signalni putovi nizvodno u karcinomima pluća čovjeka (Sandra Kraljević Pavelić, )
335-0982464-2393 - Molekularna obilježja miofibroblasta Dupuytrenove bolesti (Krešimir Pavelić, )

Ustanove
Institut "Ruđer Bošković", Zagreb,
Tekstilno-tehnološki fakultet, Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb,
Sveučilište u Rijeci - Odjel za biotehnologiju

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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