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Pregled bibliografske jedinice broj: 304532

Časopis

Autori: Gazivoda, Tatjana; Šokčević, Mario; Kralj, Marijeta; Šuman, Lidija; Pavelić, Krešimir; De Clercq, Erik; Andrei, Graciela; Snoeck, Robert; Balzarini, Jan; Mintas, Mladen; Raić-Malić, Silvana
Naslov: Synthesis and Antiviral and Cytostatic Evaluations of the New C-5 Substituted Pyrimidine and Furo[2, 3-d]pyrimidine 4', 5'-Didehydro-L-ascorbic Acid Derivatives
Izvornik: Journal of Medicinal Chemistry (0022-2623) 50 (2007), 17; 4105-4112
Vrsta rada: članak
Ključne riječi: C-5 alkynylated pyrimidines; C-6 alkylfuro[2; 3-d]pyrimidines; L-ascorbic acid; antiviral and cytostatic activity evaluations
Sažetak:
The novel C-5 alkynyl substituted pyrimidine (1-11) and furo[2, 3-d]pyrimidine derivatives (12-22) of L-ascorbic acid were synthesized by coupling of 5-iodouracil-4', 5'-didehydro-5', 6'-dideoxy-L-ascorbic acid with terminal alkynes by using Sonogashira cross-coupling reaction conditions. The new compounds were evaluated for their cytostatic and antiviral activities. Among all evaluated compounds, the octynyl-substituted uracil derivative of L-ascorbic acid (3) exhibited the most pronounced cytostatic activities against all examined tumor cell lines (IC50 = 2-12 uM). Pyrimidine derivatives of L-ascorbic acid containing p-substituted phenylacetylene groups (8-11) displayed also a rather pronounced (IC50 = 3-37 uM) inhibitory effect toward all tumor cell lines. From the bicyclic series of compounds, 6-butylfuro[2, 3-d]pyrimidine derivative (12) and 6-p-bromophenylfuro[2, 3-d]pyrimidine derivative (19) showed the highest cytostatic activity (IC50 = 4.5-20 uM), particularly against malignant leukemia (L1210) and T-lymphocyte (Molt4/C8 and CEM) cells. Compounds 3 and 9 showed specific albeit moderate activity against cytomegalovirus (CMV, Davis strain, EC50 = 1.8 and 3.8 uM, respectively, for compounds 3 and 9) at a approximately 5-fold lower concentration than that required to show cytotoxicity.
Projekt / tema: 098-0982464-2514, 098-0982464-2393, 125-0982464-2922, 125-0982464-2925
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,Temeljne medicinske znanosti
URL Internet adrese: http://pubs.acs.org/cgi-bin/abstract.cgi/jmcmar/2007/50/i17/abs/jm070324z.html
URL cjelovitog teksta:
Google Scholar: Synthesis and Antiviral and Cytostatic Evaluations of the New C-5 Substituted Pyrimidine and Furo[2, 3-d]pyrimidine 4', 5'-Didehydro-L-ascorbic Acid Derivatives
Upisao u CROSBI: Silvana Raić Malić (sraic@pierre.fkit.hr), 4. Ruj. 2007. u 15:26 sati



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