A Convenient Synthesis of 1-(omega-Aminoalkyl)-5-nitro-1H-pyrimidine-2,4-diones

• Autorzy: Węgrzynek E. , Walczak K.
• Języki publikacji: EN

Abstrakty

EN

Several monoacylated alkylene diamines have been obtained in the reaction of appropriate amine with methyl phenylacetate or ethyl formate. The monoprotected diamines were used as alkylating agents in reactions with 1-(2,4-dinitrophenyl)-5-nitrouracil. The series of hitherto unknown 1-(w-aminoalkyl)-5-nitrouracil derivatives have been obtained as a result of the uracil ring transformation. The best yield of 1-(omega-aminoalkyl)- 5-nitro - uracils was obtained when N-Boc protected alkylene diamines were applied in this reaction. The N-Boc protecting group was cleaved using diluted trifluoroacetic acid, and the liberated amines were subjected to reaction with phthalic anhydride and naphthalene 1,8-dicarboxylic anhydride.

Słowa kluczowe

EN

1,3-diaminopropane; 1,4-diaminobutane; 1,6-diaminohexane; 5-nitrouracil; phthalic anhydride; naphthalene 1,8-dicarboxylic anhydride

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2009
• Tom: Vol. 83, nr 1
• Strony: 57--64
• Opis fizyczny: Bibliogr. 29 poz., rys.

Twórcy

autor

Węgrzynek E.

autor

Walczak K.

• Department of Organic Chemistry, Biochemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland Tel. + 4832 237 1792; Fax: [phone],

Bibliografia

• 1. Block J.H. and Beale J.M., Organic Medicinal and Pharmaceutical Chemistry, 11 th ed.; Lippincott Wiliams & Wilkins: London, 2004; pp. 375,406 (2004).
• 2. Jain K.S., Chitre T.S., Miniyar P.B., Kathiravan M.K., Bendre VS., Veer VS., Shahane S.R. and Shishoo C, J. Curr. Sci., 90, 793 (2006).
• 3. Longley D.B., Harkin D.P. And Johnston P.G., Nat. Rev., 3, 330 (2003).
• 4. Hoffmann Ch., Rockstroh J.K. and Kamps B.S., HIV Medicine 2005; Flying; Steinhauser: Paris, 2005; p. 620.
• 5. Baraldi P.G., Romagnoli R., Guadix A.E., Pineda de las Infantas M.J.P., Galio M. A., Espinosa A.,Martinez A., Bingham J.P. and Hartley J.A., J. Med. Chem., 45, 3630 (2002).
• 6. Gondela A., Gabanski R. and Walczak K., Tetrahedron Lett., 45, 8007 (2004).
• 7. Gondela A. and Walczak K., Tetrahedron: Asymmetry, 16, 2107 (2005).
• 8. Inne J., Alhonen L., Pietila M. and Keinanen T.A., Eur. J. Biochem., 271, 877 (2004).
• 9. Hyrup B., Egholm M., Nielsen P.E., Wittung P., Norden B. and Buchardt O., J. Am. Chem. Soc., 116, 7964 (1994).
• 10. Krotz A.H., Larsen S., Buchardt O., Eriksson M. and Nielsen P.E., Bioorg. Med. Chem., 6,1983 (l 998).
• 11. Maison W, Schlemminger L, Westerhoe O. and Martens J., Bioorg. Med. Chem., 8, 1343 (2000).
• 12. Yu P., Wang W, Zhang H., Yang X.T., Liang Ch. and Gaoa X., Bioorg. Med. Chem., 9, 107 (2001).
• 13. Byk G. and Gilon Ch., J. Org. Chem., 57, 5687 (1992).
• 14. Guo H., Naser S.A., Ghobrial G. and Phanstiel O., J. Med. Chem., 45, 2056 (2002).
• 15. Gondela A. and Walczak K., Tetrahedron, 63, 2859 (2007).
• 16. Hirota K., Kitade Y, Sajki H. and Maki Y, J. Chem. Soc., Perkin Trans, 1, 367 (1990).
• 17. Pews R.G., Heterocycles, 27, 1867 (1988).
• 18. a) Aspinall S.R., J. Am. Chem. Soc., 62, 2160 (1940); b) Anker L., Testa B., van de Waterbeemd H.,Bornand-Crausaz A., Andreas T., Jenner P. and Marsden C.D., Helv. Chim. Acta, 66, 542 (1983).
• 19. a) Kahovec J. and Stamberg J., Coll. Czech. Chem. Commun., 42, 1838 (1977); b) Ciuffarin E. and Loi A., J. Org. Chem., 48,1047 (1983); c) Jacobson A.R., Makris A.N. and Sayre L.M., J. Org. Chem.,52,2592 (1987); d) Chen Y. and White H., Org. Prep. Proceed. Int., 28,65 (1996); e) Choi S.W., Elmaleh D.R,Hanson R.N. and Fischman A.J., J. Med. Chem., 42, 3647 (1999).
• 20. Ham J-Y and Kang H-S., Bull. Korean Chem. Soc., 15, 1025 (1994).
• 21. Zhang Z., Yin Z., Meanwell N. A., Kadow J.F. and Wang T., Org. Lett., 5, 3399 (2003).
• 22. Bender J., Meanwell N.A. and Wang T., Tetrahedron, 58, 3111 (2002).
• 23. Sabata Y, Shichita M., Sasaki K., Hashimoto Y and Iwasaki S., Chem. Pharm. Bull., 43, 177 (1995).
• 24. Lima L.M., Castro P, Machado A.L., Fraga C.A.M., Lugnier C., Gonc V.L., Moraesc A. and Barreiroa E.J.,Bioorg. Med. Chem., 10, 3067 (1995).
• 25. Chapman J.M. Jr., Cocolas G.H. and Hall I.H., J. Med. Chem., 22, 1399 (1979).
• 26. Chapman J.M. Jr., Voorstad P.J., Cocolas G.H. and Hall I.H., J. Med. Chem., 26, 237 (1983).
• 27. Orzeszko A., Kamińska B., Orzeszko G. and Starościak B.J., Il Farmaco, 55, 619 (2000).
• 28. Wamberg M.C., Walczak K., Andersen L., Hassan A.A. and Pedersen E.B., Helv. Chim. Acta, 89,1826 (2006).
• 29. Gondela A. and Walczak K., Tetrahedron Lett., 47, 4653 (2006).