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The Novel C-5 Aryl, Alkenyl and Alkynyl Substituted Uracil Derivatives of L-Ascorbic Acid: Synthesis, Cytostatic and Antiviral Activity Evaluations


Gazivoda, Tatjana; Raić-Malić, Silvana; Marjanović, Marko; Kralj, Marijeta; Pavelić, Krešimir; Balzarini, Jan; De Clercq, Erik; Mintas, Mladen
The Novel C-5 Aryl, Alkenyl and Alkynyl Substituted Uracil Derivatives of L-Ascorbic Acid: Synthesis, Cytostatic and Antiviral Activity Evaluations // Bioorganic and Medicinal Chemistry, 15 (2007), 2; 749-758 (međunarodna recenzija, članak, znanstveni)


Naslov
The Novel C-5 Aryl, Alkenyl and Alkynyl Substituted Uracil Derivatives of L-Ascorbic Acid: Synthesis, Cytostatic and Antiviral Activity Evaluations

Autori
Gazivoda, Tatjana ; Raić-Malić, Silvana ; Marjanović, Marko ; Kralj, Marijeta ; Pavelić, Krešimir ; Balzarini, Jan ; De Clercq, Erik ; Mintas, Mladen

Izvornik
Bioorganic and Medicinal Chemistry (0968-0896) 15 (2007), 2; 749-758

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

Ključne riječi
L-ascorbic acid; C-5 substituted uracil derivatives; cytostatic activities; antiviral activities

Sažetak
The novel C-5 substituted uracil derivatives of L-ascorbic acid were synthesized by coupling of 5-iodouracil-4, 5-didehydro-5, 6-dideoxy-L-ascorbic acid with unsaturated stannanes under Stille reaction conditions. The new compounds were evaluated for their antitumoral and antiviral activities. Among all compounds evaluated the 5-propynyl substituted uracil derivative of L-ascorbic acid (7) exhibited the most pronounced cytostatic activities against all examined tumor cell lines (IC50: 0.2-0.78 μ M). However, this compound was also cytotoxic to human normal fibroblasts WI 38. The 5-(phenylethynyl)uracil-2, 3-di-O-benzylated L-ascorbic acid derivative (4) exhibited an albeit slight (IC50: 55-108 μ M), but selective inhibitory effect towards all tumor cell lines except for cervical carcinoma (HeLa), pancreatic carcinoma (MiaPaCa-2), laryngeal carcinoma (Hep-2) and colon carcinoma (SW 620), and no cytotoxicity to normal human fibroblast (WI 38). Compound 7 showed some, not highly specific inhibitory potential against vesicular stomatitis virus, Coxackie B4 virus and Sindbis viruses (EC50: 1.6 μ M).

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekt / tema
098-0982464-2393 - Molekularna obilježja miofibroblasta Dupuytrenove bolesti (Krešimir Pavelić, )
098-0982464-2514 - Uloga različitih mehanizama odgovora stanica na terapiju oštećenjem DNA (Marijeta Kralj, )
125-0982464-2922 - RAZVOJ NOVIH PROLIJEKOVA I LIJEKOVA PROTIV VIRUSA I RAKA (Mladen Mintas, )
125-0982464-2925 - Razvoj i primjena novih molekula u pozitron-emisijskoj tomografiji (PET) (Silvana Raić-Malić, )

Ustanove
Institut "Ruđer Bošković", Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb

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:


  • Biological Abstracts
  • Chemical Abstracts
  • Excerpta Medica
  • Index Medicus