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Pregled bibliografske jedinice broj: 292040

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 & medicinal chemistry, 15 (2007), 2; 749-758 doi:10.1016/j.bmc.2006.10.046 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 292040 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

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 & 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


Projekti:
MZOS-098-0982464-2514 - Uloga različitih mehanizama odgovora stanica na terapiju oštećenjem DNA (Kralj, Marijeta, MZOS ) ( POIROT)
MZOS-125-0982464-2922 - RAZVOJ NOVIH PROLIJEKOVA I LIJEKOVA PROTIV VIRUSA I RAKA (Mintas, Mladen, MZOS ) ( POIROT)
MZOS-125-0982464-2925 - Razvoj i primjena novih molekula u pozitron-emisijskoj tomografiji (PET) (Raić-Malić, Silvana, MZOS ) ( POIROT)
MZOS-335-0982464-2393 - Molekularna obilježja miofibroblasta Dupuytrenove bolesti (Pavelić, Krešimir, MZOS ) ( POIROT)

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

Poveznice na cjeloviti tekst rada:

doi doi.org www.sciencedirect.com

Citiraj ovu publikaciju:

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 & medicinal chemistry, 15 (2007), 2; 749-758 doi:10.1016/j.bmc.2006.10.046 (međunarodna recenzija, članak, znanstveni)
Gazivoda, T., Raić-Malić, S., Marjanović, M., Kralj, M., Pavelić, K., Balzarini, J., De Clercq, E. & Mintas, M. (2007) The novel C-5 aryl, alkenyl, and alkynyl substituted uracil derivatives of L-ascorbic acid: Synthesis, cytostatic, and antiviral activity evaluations. Bioorganic & medicinal chemistry, 15 (2), 749-758 doi:10.1016/j.bmc.2006.10.046.
@article{article, author = {Gazivoda, Tatjana and Rai\'{c}-Mali\'{c}, Silvana and Marjanovi\'{c}, Marko and Kralj, Marijeta and Paveli\'{c}, Kre\v{s}imir and Balzarini, Jan and De Clercq, Erik and Mintas, Mladen}, year = {2007}, pages = {749-758}, DOI = {10.1016/j.bmc.2006.10.046}, keywords = {L-ascorbic acid, C-5 substituted uracil derivatives, cytostatic activities, antiviral activities}, journal = {Bioorganic and medicinal chemistry}, doi = {10.1016/j.bmc.2006.10.046}, volume = {15}, number = {2}, issn = {0968-0896}, title = {The novel C-5 aryl, alkenyl, and alkynyl substituted uracil derivatives of L-ascorbic acid: Synthesis, cytostatic, and antiviral activity evaluations}, keyword = {L-ascorbic acid, C-5 substituted uracil derivatives, cytostatic activities, antiviral activities} }
@article{article, author = {Gazivoda, Tatjana and Rai\'{c}-Mali\'{c}, Silvana and Marjanovi\'{c}, Marko and Kralj, Marijeta and Paveli\'{c}, Kre\v{s}imir and Balzarini, Jan and De Clercq, Erik and Mintas, Mladen}, year = {2007}, pages = {749-758}, DOI = {10.1016/j.bmc.2006.10.046}, keywords = {L-ascorbic acid, C-5 substituted uracil derivatives, cytostatic activities, antiviral activities}, journal = {Bioorganic and medicinal chemistry}, doi = {10.1016/j.bmc.2006.10.046}, volume = {15}, number = {2}, issn = {0968-0896}, title = {The novel C-5 aryl, alkenyl, and alkynyl substituted uracil derivatives of L-ascorbic acid: Synthesis, cytostatic, and antiviral activity evaluations}, keyword = {L-ascorbic acid, C-5 substituted uracil derivatives, cytostatic activities, antiviral activities} }

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


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