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Pregled bibliografske jedinice broj: 394782

Časopis

Autori: Benci, Krešimir; Wittine, Karlo; Radan, Malajka; Cetina, Mario; Sedić, Mirela; Kraljević Pavelić, Sandra; Pavelić, Krešimir; deClercq, Erik; Mintas, Mladen
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
Izvornik: Bioorganic & medicinal chemistry (0968-0896) 18 (2010), 17; 6249-6257
Vrsta rada: članak
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.
Projekt / tema: 119-1193079-3069, 335-0982464-2393, 125-0982464-2922, 335-0000000-3532
Izvorni jezik: ENG
Rad je indeksiran u
bazama podataka:
Current Contents Connect (CCC)
MEDLINE
Scopus
SCI-EXP, SSCI i/ili A&HCI
Science Citation Index Expanded (SCI-EXP) (sastavni dio Web of Science Core Collectiona)
Kategorija: Znanstveni
Znanstvena područja:
Kemija,Temeljne medicinske znanosti
URL Internet adrese: http://dx.doi.org/10.1016/j.bmc.2010.07.035
http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6TF8-50K5SXK-1-R&_cdi=5220&_user=3875467&_pii=S0968089610006887&_origin=browse&_zone=rslt_list_item&_coverDate=09%2F01%2F2010&_sk=999819982&wchp=dGLbVzb-zSkzS&md5=00c37fe17227a33496ea3ea8d24291f9&ie=/sdarticle.pdf
http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TF8-50K5SXK-1&_user=3875467&_coverDate=09%2F01%2F2010&_rdoc=6&_fmt=high&_orig=browse&_origin=browse&_zone=rslt_list_item&_srch=doc-info(%23toc%235220%232010%23999819982%232271735%23FLA%23display%23Volume)&_cdi=5220&_sort=d&_docanchor=&_ct=42&_acct=C000050661&_version=1&_urlVersion=0&_userid=3875467&md5=726c63787f586b1b52b423c4e876098f&searchtype=a
Broj citata:
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DOI: 10.1016/j.bmc.2010.07.035
URL cjelovitog teksta: http://dx.doi.org/10.1016/j.bmc.2010.07.035
Google Scholar: 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
Upisao u CROSBI: mmintas@fkit.hr (mmintas@fkit.hr), 28. Svi. 2009. u 10:06 sati



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