Syntheses and In Vitro Antitumor Activity of 3-Amino-N-(4-chlorobenzenesulfonyl)guanidine Derivatives Containing N'-Arylidene Moiety

• Autorzy: Sławiński J. , Bednarski P. , Reszka P.
• Języki publikacji: EN

Abstrakty

EN

The syntheses of new 3-arylideneamino-1-(2-alkythio-4-chloro-5-methylbenzenesulfonyl) guanidines 2-8 and 1-arylidene-2-(2-alkylthio-4-chloro-5-R3-benzenesulfonyl)- 3-methylaminoguanidines 9-16 are described. The in vitro antitumor screening of compounds 2, 3, 9 and 10 was evaluated at the Institute of Pharmacy, University of Greifswald. The remaining compounds 5, 11-14 and 16 were screened at the National Cancer Institute (NCI) for their activities against a panel of 55 human tumor cell lines, and relationships between structure and anticancer activity in vitro are discussed. The highest anticancer activity was found for 2-(2-benzylthio-4-chloro-5-methylbenzenesulfonyl)- 3-methylamino-1-(5-nitrothienylidene)guanidine (12) (GI50 in the range 0.3-0.6 _M), while other compounds exhibit reasonable (16) or moderate ( 9, 13) anticancer activities.

Słowa kluczowe

EN

3-amino-N-(benzenesulfonyl)guanidines; synthesis; anticancer activity

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2004
• Tom: Vol. 78 / nr 3
• Strony: 369--379
• Opis fizyczny: Bibliogr. 20 poz., rys.

Twórcy

autor

Sławiński J.

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

autor

Bednarski P.

• Department of Pharmaceutical and Medicinal Chemistry, Institute of Pharmacy, University of Greifswald, L.-John Str. 17, D-17487 Greifswald, Germany

autor

Reszka P.

• Department of Pharmaceutical and Medicinal Chemistry, Institute of Pharmacy, University of Greifswald, L.-John Str. 17, D-17487 Greifswald, Germany

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. Scozzafava A., Casini A. and Supuran C.T., Curr. Med. Chem., 9, 1167 (2002).
• 4. Supuran C.T., Casini A. and Scozzafava A., Med. Res. Rev., 23, 535 (2003).
• 5. Artico M„ Il Farmaco, 51, 305 (1996).
• 6. Leung D., Abbenante G. and Fairlie D., J. Med. Chem., 43, 305 (2000).
• 7. Vermeire K., Bell T.W., Choi H.J., Jin Q., Samala M.F., Sodoma A., de Clercq E. and Schols D., Mol. Pharmacol., 63, 203 (2003).
• 8. Chem J., Leu Y., Wang S., Jou R., Lee C., Tsou P., Hsu S., Liaw Y. and Lin H., J. Med. Chem., 40,2276 (1997).
• 9. Pindur U. and Lemster T., Pharmazie, 53, 79 (1998).
• 10. Stanek J., Caravatti G., Capraro H-G., Furet P., Mett H., Schneider R and Regenass U., J. Med. Chem., 36, 46(1993).
• 11. Stanek J., Caravatti G., Frei J., Furet R, Mett H., Schneider R and Regenass U., J. Med. Chem., 36,2168 (1993) .
• 12. Matsumo S., Myaguchi M., Ito A., HaraN. and SakuradaN., Jpn. Pat. 06,192,215; C.A., 121, 300598t (1994) .
• 13. Stawinski J., Bednarski P., Grunert R. and Reszka P., Polish J. Chem., 77, 53 (2003).
• 14. Brzozowski Z. and S^czcwski F., Eur. J. Med. Chem., 37,285 (2002).
• 15. Bernhardt G., Reile H., Bimbock H., SpruB T. and Schonenberger H., J. Cancer Res. Clin. Oncol., 118, 35 (1992).
• 16. Details of this system and the information which is encoded by the activity pattern over all cell lines have been also described in our previous paper ref. [13].
• 17. Boyd M.R., Am. Assoc. Cancer Res., 30, 652 (1989).
• 18. Monks A.P., Scudiero D.A., Skehan P., Shoemaker K.D., Poull D., Vistica C., Hose C., Langley J., Cronise P., Vaigro-Wolff A., Gray-Goodrich M., Cambell H., Mayo M. and Boyd M., J. Natl. Cancer Inst., 83, 757(1991).
• 19. Weinstein J.N., Myers T.G., O'Connor P.M., Friend S.H., Fomance A.J., Jr., Kohn K.W., Fojo T., Bates S.E., Rubinstein L.V., Anderson N.L., Buolamwini J.K., van Osdol W.W., Monks A.P., Scudiero D.A., Sausiville E.A., Zaharevitz D.W., Bunow B., Viswanadhan V.N., Johnson G.S., Wittes R.E. and Pauli K.D., Science, 275, 343 (1997).
• 20. Stawinski I., Polish! Chem., 75, 1309 (2001).