An efficient synthesis of cytostatic mono and bis-alkynylpyrimidine derivatives by the Sonogashira cross-coupling reactions of 2,4-diamino-6- iodopyrimidine and 2-amino-4,6-dichloropyrimidine

Tetrahedron

Volumn 60, Issue 23, 2004, Pages 4983-4987

  Hocková, Dana ^a   Holý, Antonín ^a   Masojídková, Milena ^a   Votruba, Ivan ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Alkynes; Cross coupling; Cytostatic activity; Pyrimidines; Sonogashira reaction

Indexed keywords

2 AMINO 4,6 DICHLOROPYRIMIDINE; 2,4 DIAMINO 6 IODOPYRIMIDINE; 4,6 ALKYNYL 2 AMINOPYRIMIDINE; ALKYNE; ALKYNYLPYRIMIDINE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CROSS COUPLING REACTION; CYTOSTASIS; PRIORITY JOURNAL; SONOGASHIRA REACTION;

EID: 2442556117     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.04.035     Document Type: Article

References (18)

1. Stang P.J., Diederich F. Modern Acetylene Chemistry. 1995;VCH, Weinheim, Germany
2. Patai S. Chemistry of Triple-Bonded Functional Groups. 1994;Wiley, New York
3. Lee S.E., Sidorov A., Gourlain T., Mignet N., Thorpe S.J., Brazier J.A., Dickman M.J., Hornby D.P., Grasby J.A., Williams D.M. Nucleic Acids Res. 29:2001;1565-1573
4. Lam J., Breteler H., Arnason T., Hansen L. Chemistry and Biology of Naturally-Occurring Acetylenes and Related Compounds. 1988;Elsevier, Amsterdam
5. Negishi E., Anastasia L. Chem. Rev. 103:2003;1979-2017
6. Sonogashira K. Negishi E. Handbook of Organopalladium Chemistry for Organic Synthesis. 2002;493-529 Wiley-Interscience, New York
7. Hocková D., Holý A., Masojídková M., Andrei G., Snoeck R., De Clercq E., Balzarini J. J. Med. Chem. 46:2003;5064-5073
8. Hocková, D; Holý, A; Masojídková, M; Andrei, G; Snoeck, R; De Clercq, E; Balzarini, J. Bioorg. Med. Chem. 2004. Submitted for publication.
9. Gomtsyan A., Didomenico S., Lee C.-H., Matulenko M.A., Kim K., Kowaluk E.A., Wismer C.T., Mikusa J., Yu H., Kohlhaas K., Jarvis M.F., Bhagwat S.S. J. Med. Chem. 45:2002;3639-3648
10. Hocek M., Dvořák D., Havelková M. Nucleosides Nucleotides Nucleic Acids. 22:2003;775-777
11. Hocek M., Dvořáková H., Císarová I. Collect. Czech. Chem. Commun. 67:2002;1560-1578
12. Shen B., Liu W., Nonaka K. Curr. Med. Chem. 10:2003;2317-2325
13. Basak A., Mandal S., Bag S.S. Chem. Rev. 103:2003;4077-4094
14. Cooke G., de Cremiers H.A., Rotello V.M., Tarbit B., Vanderstraeten P.E. Tetrahedron. 57:2001;2787-2789
15. Wendelin W., Zmoelnig I., Schramm H.F. Monatsh. Chem. 111:1980;1189-1191
16. Landor S.R., Landor P.D., Williams V.E. J. Chem. Soc., Perkin Trans. 1. 1984;2677-2679
17. Hocek M., Holý A., Votruba I., Dvořáková H. J. Med. Chem. 43:2000;1817-1825
18. Scudiero D.A., Shoemaker R.H., Paull K.D., Monks A., Tierney S., Nofziger T.H., Currens M.J., Seniff D., Boyd M.R. Cancer Res. 48:1988;4827-4833