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Pregled bibliografske jedinice broj: 108897

Časopis

Autori: Prekupec, Svjetlana; Svedružić, Draženka; Gazivoda, Tatjana; Mrvoš-Sermek, Draginja; Nagl, Ante; Grdiša, Mira; Pavelić, Krešimir; Balzarini, Jan; De Clercq, Erik; Folkers, Gerd; Scapozza, Leonardo; Mintas, Mladen; Raić-Malić, Silvana
Naslov: Synthesis and Biological Evaluation of Iodinated and Fluorinated 9-(2-Hydroxypropyl) and 9-(2-Hydroxyethoxy)methyl Purine Nucleoside Analogues
Izvornik: Journal of Medicinal Chemistry (0022-2623) 46 (2003), 26; 5763-5772
Vrsta rada: članak
Ključne riječi: purine nucleoside analogues; diazotation; iodination; Baltz-Schiemann fluorination; citostatic activity; x-ray crystallography
Sažetak:
The novel fluorinated and iodinated purine derivatives containing 9-(2-hydroxypropyl)- (1a-7a, and 9a-13a) and 9-(2-hydroxyethoxymethyl)- (1b-3b, 5b and 7b-12c) side chains were synthesized by multistep synthetic route involving Baltz-Schiemann's fluorination and diazotation/iodination as key reactions. An unequivocal proof for the stereostructure of 5b was obtained by X-ray structure analysis. New compounds were evaluated for their cytostatic activity against murine leukaemia (L1210/0), mammary carcinoma (FM3A/0) and human T-lymphocytes (Molt4/C8 and CEM/0), melanoma (HBL), cervical carcinoma (HeLa), colon carcinoma (HT29 and SW620), laryngeal carcinoma (Hep2), pancreatic carcinoma (MiaPaCa2) as well as diploid fibroblasts (WI38). Of all the compounds, the 2-aminopurin-6-thione derivative 9a showed the most pronounced inhibitory activity against human SW620 cells. The 2-aminopurin-6-thione derivative 9b exhibited marked selectivity in cytostatic activity. It inhibited specifically the proliferation of human HeLa, Hep2 and SW620 cells but not of the other ones. None of the compounds showed inhibitory activities against HIV-1, HIV-2, HSV-1 and HSV-2, vaccinia, vesicular stomatitis, parainfluenza-3, reovirus-1, Sindbis, Coxsackie B4 or respiratory syncytial virus.
Projekt / tema: 0098093, 0125003
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
URL cjelovitog teksta:
Google Scholar: Synthesis and Biological Evaluation of Iodinated and Fluorinated 9-(2-Hydroxypropyl) and 9-(2-Hydroxyethoxy)methyl Purine Nucleoside Analogues



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