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Pregled bibliografske jedinice broj: 108897

Synthesis and Biological Evaluation of Iodinated and Fluorinated 9-(2-Hydroxypropyl) and 9-(2-Hydroxyethoxy)methyl Purine Nucleoside Analogues


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 (međunarodna recenzija, članak, znanstveni)


Naslov
Synthesis and Biological Evaluation of Iodinated and Fluorinated 9-(2-Hydroxypropyl) and 9-(2-Hydroxyethoxy)methyl Purine Nucleoside Analogues

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

Izvornik
Journal of Medicinal Chemistry (0022-2623) 46 (2003), 26; 5763-5772

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

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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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


Uključenost u ostale bibliografske baze podataka:


  • Chemical Abstracts
  • Index Medicus