Synthesis, structural studies and antitumoral evaluation of C-6 alkyl and alkenyl side chain pyrimidine derivatives

Molecules

Volumn 14, Issue 12, 2009, Pages 4866-4879

  Krištafor, Svjetlana ^a   Kraljević, Tatjana Gazivoda ^a   Makuc, Damjan ^b   Plavec, Janez ^b   Šuman, Lidija ^c   Kralj, Marijeta ^c   Raić Malić, Silvana ^a  

^a UNIVERSITY OF ZAGREB   (Croatia)

^b NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

^c RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

C 6 alkyl and alkenyl pyrimidine derivatives; Cytostatic activity evaluations; NMR conformational analysis

Indexed keywords

ANTINEOPLASTIC AGENT; PYRIMIDINE; PYRIMIDINE DERIVATIVE;

ARTICLE; CELL CYCLE; CHEMISTRY; HUMAN; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL CYCLE; CELL LINE, TUMOR; CHROMATOGRAPHY, THIN LAYER; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PYRIMIDINES;

EID: 73849097626     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14124866     Document Type: Article

References (18)

1. Böhm, H.J.; Banner, D.; Bendels, S.; Kansy, M.; Kuhn, B.; Müller, K.; Obst-Sander, U.; Stahl, M. Fluorine in medicinal chemistry. ChemBioChem 2004, 5, 637-643.
2. Dolbier, W.R., Jr. Fluorine chemistry at the millennium. J. Fluorine Chem. 2005, 126, 157-163.
3. Isanbor, C.; O'Hagan, D. Fluorine in medicinal chemistry: A review of anti-cancer agents. J. Fluor. Chem. 2006, 127, 303-319.
4. Howard, J.A.K.; Hoy, V.J.; O'Hagan, D.; Smith, G.T. How good is fluorine as a hydrogen bond acceptor? Tetrahedron 1996, 52, 12613-12622.
5. Bergstrom, D.E.; Swartling, D.J. Structure, Reactivity, Synthesis and Applications. In Fluorine-Containing Molecules; Liebman, J.F.; Greenberg, A.; Dolbier, W.R., Jr., Eds.; VCH: New York, NY, USA, 1988; pp. 259-308.
6. Öǧretir, C.; Yaman, M. AM1, PM3 and MNDO study of the tautomeric equilibria of 2-, 4- or 5-hydroxypyrimidin derivatives and their azo- and thio-analogs. J. Mol. Struct. (Theochem) 1999, 458, 217-226.
7. Williams, M.; Kowaluk, E.A.; Arneric, S.P. Emerging molecular approaches to pain therapy. J. Med. Chem. 1999, 42, 1481-1500.
8. Bradshaw, T.K.; Hutchinson, D.N. 5-Substituted pyrimidine nucleosides and nucleotides. Chem. Soc. Rev. 1977, 6, 43-62.
9. Prekupec, S.; Makuc, D.; Plavec, J.; Kraljević, S.; Kralj, M.; Pavelić, K.; Andrei, G.; Snoeck, R.; Balzarini, J.; De Clercq, E.; Raić-Malić, S.; Mintas, M. Antiviral and cytostatic evaluation of the novel 6-acyclic chain substituted thymine derivatives. Antiviral Chem. Chemother. 2005, 16, 327-338.
10. Prekupec, S.; Makuc, D.; Plavec, J.; Šuman, L.; Kralj, M.; Pavelić, K.; Balzarini, J.; De Clercq, E.; Mintas, M.; Raić-Malić, S. Antiviral and cytostatic evaluation of the novel 6-acyclic chain substituted thymine derivatives. J. Med. Chem. 2007, 50, 3037-3045.
11. Shields, A.F.; Lim, K.; Grierson, J.; Link, J.; Krohn, K.A. Utilization of Labeled Thymidine in DNA Synthesis: Studies for PET. J. Nucl. Med. 1990, 31, 337-342.
12. Schlenker, J. Ueber 4.5-Dimethylpyrimidin. Berichte 1901, 34, 2812-2829.
13. 18F-radiolabelling and biological evaluations of C-6 alkylated pyrimidine nucleoside analogues. Nucleos. Nucleot. Nucleic. Acids 2004, 23, 1707-1721.
14. Middleton, W.J. New fluorinating reagents. Dialkylaminosulfur fluorides. J. Org. Chem. 1975, 40, 574-578.
15. Agrofoglio, L.A.; Gillaizeau, I.; Saito, Y. Palladium-Assisted routes to nucleosides. Chem. Rev. 2003, 103, 1875-1916.
16. Stille, J.K. The Palladium-catalyzed Cross-coupling reactions of organotin reagents with organic electrophiles [New Synthetic Methods (58)]. Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524.
17. Stille, J.K. Palladium catalyzed coupling of organotin reagents with organic electrophiles. Pure Appl. Chem. 1985, 57, 1771-1780.
18. Gazivoda, T.; Krištafor, S.; Cetina, M.; Nagl, A.; Raić-Malić, S. Synthesis and structural studies of C-5 aryl and C-6 alkyl substituted pyrimidine derivatives. Struct. Chem. 2008, 19, 441-449.