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1-(2,4-Dinitrophenyl)-5-nitrouracil a Versatile Reagent for the Synthesis of N1-Modified Uracil Derivatives

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Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
1-(2,4-Dinitrophenyl)-5-nitrouracil has been used as a substrate in reactions with a number of compounds possessing primary amino groups such as: amino alcohols, aminodiols, esters of amino ac ids and benzylamines. As a result of regioselective course of performed reactions the series of 5-nitro-1-substituted uracils were obtained. All newly synthesized compounds were subjected to primary bioactivity as says as inhibitors against Mycobacterium tuberculosis; two of them exhibited inhibition ability.
Rocznik
Strony
2143--2149
Opis fizyczny
Bibliogr. 13 poz., rys.
Twórcy
autor
autor
autor
  • Department of Organic Chemistry, Biochemistry and Biotechnology, Silesian University of Technology,Krzywoustego 4, 44-100 Gliwice, Poland Tel. + 4832 237 1792; Fax: +4832 237 2094, Krzysztof.Walczak@polsl.pl
Bibliografia
  • 1. a) Block J.H. and Beale J.M., in: Organic Medicinal and Pharmaceutical Chemistry, 11th ed. Lippincott Williams & Wilkins, London, pp. 375-382 and 406-414 (2004); b) Tanaka H., Takashima H., Ubasawa M., Sekiya K., Nitta L, Baba M., Shigeta S., Walker R.T., De Clereq E. and Miyasaka T., J. Med. Chem., 35, 337 (1992); c) Baba M., Shigeta S., Yuasa S., Takashima H., Sekiya K., Ubasawa M., Tanaka H., Miyasaka T., Walker R.T. and De Clercą E., Antimicrob. Agents Chemother., 38,688 (1994); d) Petersen L., Hansen T.H., Khalifa N.M., Jǿrgensen P.T., Pedersen E.B. and Nielsen C., Monatsh. Chem., 133, 1031(2002).
  • 2. Hoffmann Ch., Rockstroh J.K. and Kamps B.S., in: HIV Medicine 2005, Flying Publisher; Paris, Steinauser Verlag, p. 620 (2005).
  • 3. Longley B.D., Harkin D.P. and Johnston P.G., Nature Rev., 3, 330 (2003).
  • 4. Baraldi P.G., Romagnoli R., Guadbe 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).
  • 5. a) More J.C.A., Troop H.M. and Jane D.E., British J. Pharm., 137,1125 (2002); b) Dolman N.P., More J.C.A., Alt A., Knaus J.L., Troop H.M., Bleakman D., Collingridge G.L. and Jane D.E., J. Med. Chem.,49, 2579 (2006).
  • 6. Hyrup B., Egholm M., Nielsen P.E., Wittung P., Norden B. and Buchardt O., J. Am. Chem. Soc., 116, 7964(1994).
  • 7. a) Hyrup B. and Nielsen P.E., Bioorg. Med. Chem., 4, 5 (1996); b) Ganesh K.N. and Nielsen P.E., Curr. Org. Chem..,8,931(2000).
  • 8. a) Efimtseva E.V., Mikhailov S.N., Meshkov S., Hankamaki T., Oivanen M. and Lomberg H., J. Chem. Soc. Perkin Trans, 1, 1409 (1995); b) Cadet C.,Chan Ch.S., Daniel R.Y, Davis C.P., Guiadeen D., Rodriguez G., Thomas T., Walcott S. and Scheiner P., J. Org. Chem., 63, 4574 (1998).
  • 9. a) Hirota K., Kitade Y, Sajki H. and Maki Y, J. Chem. Soc. Perkin Trans, 1, 367 (1990); b) Gondela A. and Walczak K., Tetrahedron Lett., 44, 7291 (2003).
  • 10. Gondela A. and Walczak K., Tetrahedron Lett., 47, 4653 (2006).
  • 11. Gondela A. and Walczak K., Tetrahedron Asymm., 16, 2107 (2005).
  • 12. Kundu N.G., Sikhar S., Hertzberg R.P., Schmitz S.A. and Khatri S.G., J. Chem. Soc. Perkin Trans, 1, 1295 (1985).
  • 13. Novikov M.S. and Ozerov A.A., Chem. Heterocycl. Compd., 41, 766 (2005).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ6-0023-0087
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