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Synthesis and biological evaluation of iodinated and fluorinated 9-(2-hydroxypropyl) and 9-(2-hydroxyethoxy)methyl purine nucleoside analogues (CROSBI ID 99096)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Prekupec, Svjetlana ; Svedružić, Draženka ; Gazivoda, Tatjana ; Mrvoš-Sermek, Draginja ; Nagl, Ante ; Grdiša, Mira ; Pavelić, Krešimir ; Balzarini, Jan ; De Clercq, Erik ; Folkers, Gerd et al. Synthesis and biological evaluation of iodinated and fluorinated 9-(2-hydroxypropyl) and 9-(2-hydroxyethoxy)methyl purine nucleoside analogues // Journal of medicinal chemistry, 46 (2003), 26; 5763-5772. doi: 10.1021/jm0308747

Podaci o odgovornosti

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

engleski

Synthesis and biological evaluation of iodinated and fluorinated 9-(2-hydroxypropyl) and 9-(2-hydroxyethoxy)methyl purine nucleoside analogues

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.

purine nucleoside analogues ; diazotation ; iodination ; Baltz-Schiemann fluorination ; citostatic activity ; x-ray crystallography

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Podaci o izdanju

46 (26)

2003.

5763-5772

objavljeno

0022-2623

1520-4804

10.1021/jm0308747

Povezanost rada

Kemija

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