Syntheses of 1-(phenylsulfonyl)-(1H, 3H)-imidazol-2-one Derivatives with Potential Biological Activity

• Autorzy: Brzozowski Z. , Sławiński J.
• Języki publikacji: EN

Abstrakty

EN

Aseries of 1-(arylsulfonyl)-3-(2,2-dimethoxyethyl)ureas (2a-e) was obtained by the reaction of 1-(phenylsulfonyl)ureas (1a-e) with aminoacetaldehyde dimethyl acetal in boiling dioxane. Cyclocondensation reactions of the 1-(arylsulfonyl)-3-(2,2-dimethoxyethyl) ureas (2a-e) in 98% H2SO4 gave the appropriate 1-(arylsulfonyl)-(1H,3H)- imidazol-2-ones (3a-e) in good yields. The subsequent reaction of 3a with methanesulfonyl- or 4-nitrophenylsulfonyl chlorides furnished the 3-(R4-sulfonyl) derivatives 4 and 5, respectively. Preliminary screening data indicated that the compounds 3c-e, 4 and 5 were inactive against three selected human tumor cell lines derived from Breast cancer (MCF7), Lung cancer (NCI-H460) and CNS cancer (SF-268).

Słowa kluczowe

EN

1-(phenylsulfonyl)-(1H,3H)-imidazol-2-ones; synthesis; antitumor effect

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2004
• Tom: Vol. 78 / nr 4
• Strony: 547--551
• Opis fizyczny: Bibliogr. 15 poz., rys.

Twórcy

autor

Brzozowski Z.

• Department of Chemical Technology of Drugs, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, Poland

autor

Sławiński J.

• Department of Chemical Technology of Drugs, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, Poland

Bibliografia

• 1. Casini A., Scozzafava A., Mastrolorenzo A. and Supuran C.T., Curr. Cancer Drug Targets, 2,55 (2002).
• 2. Scozzafava A., Owa T., Mastrolorenzo A. and Supuran C.T., Curr. Med. Chem., 10, 925 (2003).
• 3. Supuran C.T., Casini A. and Scozzafava A., Med. Res. Rev., 23, 535 (2003).
• 4. Huang Z., Lin Z. and Huang I., Eur. J. Med. Chem., 36, 863 (2001).
• 5. Pomamacka E. and Gdaniec M., Bioorg. Med. Chem., 11, 1259 (2003).
• 6. Brzozowski Z. and Sączewski F., J. Med. Chem., 45, 430 (2002).
• 7. Brzozowski Z., Sączewski F. and Gdaniec M., Eur. J. Med. Chem., 37, 285 (2002).
• 8. Brzozowski Z., Sączewski F. and Gdaniec M., Bioorg. Med. Chem., 11, 3673 (2003).
• 9. Brzozowski Z., Sączewski F. and Gdaniec M., Eur. J. Med. Chem., 38, 991 (2003).
• 10. Sławiński J., Bednarski P., Grtinert R. and Reszka P., Polish J. Chem., 77, 53 (2003).
• 11. Sławiński J., Eur. J. Med. Chem., 39, in press (2004).
• 12. Kuo Ch.L., Assefa H., Kamath S., Brzozowski Z., Sławiński J., Sączewski F., Buolamwini J.K. and Neamati N„ J. Med. Chem., 47, 385 (2004).
• 13. Howbert J., Grossman C.S., Crowell T.A., Rieder B.J., Harper R.W., Kramer K.E., Tao E.V., Aikins J., Poore G.A., Rinzel S.M., Grindey G.B., Shaw W.N. and Todd G.C.,7 Med. Chem., 33, 293 (1990).
• 14. Artico M., Silvestri R., Massa S., Loi A.G., Corrias S., Piras G. and Colla P.L., J. Med. Chem., 39, 522 (1996).
• 15. Brzozowski Z., Acta Polon. Pharm.-Drug Res., 55, 233 (1998).