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Pregled bibliografske jedinice broj: 36944

Časopis

Autori: Raić-Malić, Silvana; Hergold-Brundić, Antonija; Nagl, Ante; Grdiša, Mira; Pavelić, Krešimir; De Clercq, Erik; Mintas, Mladen
Naslov: Novel pyrimideine and purine derivatives of L-ascorbic acid : synthesis and biological evaluation
Izvornik: Journal of medicinal chemistry (0022-2623) 42 (1999), 14; 2673-2678
Vrsta rada: članak
Ključne riječi: pyrimidine and purine derivatives; L-ascorbic acid; Murine leukemia (L1210/0); Murine mammary carcinoma (FM3A); Human T-lymphocytes (Molt4/C8 and CEM/0); Varicella-zoster virus (VZV); Cytomegalovirus (CMV)
Sažetak:
The novel pyrimidine derivatives 1-6 of 2, 3-dibenzyl-4, 5-didehydro-5, 6-didehydro-5, 6-dideoxy-L-ascorbic acid were synthesized by the condensation of pyrimidine bases with 5, 6-diacetyl-2, 3-dibenzyl-L-ascorbic acid (DDA). Both N-9 (7) and N-7 (8) regioisomers were obtained in the reaction of 6-chloropurine with 5-acetyl-6-bromo-2, 3-dibenzyl-L-ascorbic acis (ABDA), while the reaction of 6-(N-pyrroly)purine with ABDA afforded exclusively the N-9 isomer 9. Structures of all newly prepared compounds were deduced from the chemical shifts in 1H and 13C NMR spectra, as well as connectivities in 2D homo- and heteronuclear correlation spectra. An unambiguous proof of the structure and conformation of 7 was obtained by X-ray crystallographic analysis. Compounds 1-9 were found to exert cytostatic activities against malignant cell lines: pancreatic carcinoma (MiaPaCa2), breast carcinoma (MCF7), cercival carcinoma (HeLa), laryngeal carcinoma (Hep2), murine leukemia (L1210/0), murine mammary carcinoma (FM3A), and human T-lymphocytes (Molt4/C8 and CEM/0), as well as antiviral activities against varicella-zoster virus (TK+VZV and TK-VZV) and cytomegalovirus (CMV). The compound 6 containing a triofluoromethyl-substituted uracil ring exhibited marked antitumor activity. The N-7-substituted purine regioisomer 8 had greater inhibitory effects on the murine L1210/0 and human CEM/0 cell lines than the N-9 isomer 7. Compound 9 with the 6-purine-substituted pyrrolo moiety had a more pronounced selective cytostatic activity against human (Molt4/C8 and CEM/0) cell lines than murine (L1210/0 and FM3A/0) and human (MiaPaCa2, MCF7, HeLa, and hep2) tumor cell lines and normal fibroblasts (Hef522). The compound 6 exhibited the most potent antiviral activities against TK+VZV, TK-VZV, and CMV, albeit at concentrations that were only slightly lower than the cytotoxic concentrations.
Projekt / tema: 00981104, 125003
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 Internet adrese: http://pubs.acs.org/doi/abs/10.1021/jm991017z
Broj citata:
Altmetric:
DOI: 10.1021/jm991017z
URL cjelovitog teksta:
Google Scholar: Novel pyrimideine and purine derivatives of L-ascorbic acid : synthesis and biological evaluation



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