Synthesis and antiproliferative activity of basic thioanalogues of merbarone

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 12, 2003, Pages 2575-2589

  Ranise, Angelo ^a   Spallarossa, Andrea ^a   Schenone, Silvia ^a   Bruno, Olga ^a   Bondavalli, Francesco ^a   Pani, Alessandra ^b   Marongiu, Maria Elena ^b   Mascia, Valeria ^b   La Colla, Paolo ^b   Loddo, Roberta ^b  

^a UNIVERSITY OF GENOA   (Italy)

^b UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,3,5 TRIPHENYL 6 [(2 PIPERIDIN 1 YLETHYL)THIO] 2 THIOXO 2,3 DIHYDROPYRIMIDIN 4(1H) ONE; 1,3,5 TRIPHENYL 6 [(2 PYRROLIDIN 1 YLETHYL)THIO] 2 THIOXO 2,3 DIHYDROPYRIMIDIN 4(1H) ONE; 5 ACETYL 1,3 DIPHENYL 6 [(2 PYRROLIDIN 1 YLETHYL)THIO] 2 THIOXO 2,3 DIHYDROPYRIMIDIN 4(1H) ONE; 5 ACETYL 1,3 DIPHENYL 6 [(3 PIPERIDIN 1 YLPROPYL)THIO] 1,3 DIPHENYL 2 THIOXO 2,3 DIHYDROPYRIMIDN 4(1H) ONE; 5 ACETYL 6 [(2 DIMETHYLAMINOETHYL)THIO] 1,3 DIPHENYL 2 THIOXO 2,3 DIHYDROPYRIMIDIN 4(1H) ONE; 5 IMINO 1,3,6 TRIPHENYL 7 [(2 PIPERIDIN 1 YLETHYL)THIO] 5,6 DIHYDROPYRIMIDO[4,5 D]PYRIMIDINE 2,4(1H,3H) DITHIONE; 5 IMINO 1,3,6 TRIPHENYL 7 [(2 PYRROLIDIN 1 YLETHYL)THIO] 5,6 DIHYDROPYRIMIDO[4,5 D]PYRIMIDINE 2,4(1H,3H) DITHIONE; 5 IMINO 1,3,6 TRIPHENYL 7 [(3 PIPERIDIN 1 YLPROPYL)THIO] 5,6 DIHYDROPYRIMIDO[4.5 D]PYRIMIDIN 2,4(1H,3H) DITHIONE; 5 IMINO 7 [(2 MORPHOLIN 4 YLETHYL)THIO] 1,3,6 TRIPHENYL 5,6 DIHYDROPYRIMIDO[4,5 D]PYRIMIDINE 2,4(1H,3H) DITHIONE; 6 [(2 DIETHYLAMINOETHYL)THIO] 1,3,4 TRIPHENYL 2 THIOXO 2,3 DIHYDROPYRIMIDIN 4(1H) ONE; 6 [(2 MORPHOLIN 4 YLETHYL)THIO] 1,3,5 TRIPHENYL 2 THIOXO 2,3 DIHYDROPYRIMIDIN 4(1H) ONE; 6 [(3 DIMETHYLAMINOPROPYL)THIO] 1,3,3 TRIPHENYL 2 THIOXO 2,3 DIHYDROPYRIMIDIN 4(1H) ONE; 6 [[3 (DIMETHYLAMINO) 2 METHYLPROPYL]THIO] 1,3,5 TRIPHENYL 2 THIOXO 2,3 DIHYDROPYRIMIDIN 4(1H) ONE; 6 [[3 [4 (3 CHLOROPHENYL)PIPERAZIN 1 YL]PROPYL]THIO] 1,3,5 TRIPHENYL 2 THIOXO 2,3 DIHYDROPYRIMIDIN 4(1H) ONE; 7 [(2 DIETHYLAMINOETHYL)THIO] 5 IMINO 1,3,6 TRIPHENYL 5,6 DIHYDROPYRIMIDO[4.5 D]PYRIMIDINE 2,4(1H,3H) DITHIONE; 7 [(2 DIMETHYLAMINOETHYL)THIO]5 IMINO 1,3,6 TRIPHENYL 5,6 DIHYDROPYRIMIDO[4,5 D]PYRIMIDINE 2,4(1H,3H) DITHIONE; 7 [(3 DIMETHYLAMINOPROPYL)THIO] 5 IMINO 1,3,6 TRIPHENYL 5,6 DIHYDROPYRIMIDO[4,5 D]PYRIMIDIN 2,4(1H,3H) DITHIONE; 7 [[3 (DIMETHYLAMINO) 2 METHYLPROPYL]THIO] 5 IMINO 1,3,6 TRIPHENYL 5,6 DIHYDROPYRIMIDO[4,5 D]PYRIMIDIN 2,4(1H,3H) DITHIONE; ANTIMITOTIC AGENT; ANTINEOPLASTIC AGENT; ETHYL 1,3 DIPHENYL 6 [(3 PIPERIDIN 1 YLPROPYL)THIO] 4 OXO 2 THIOXO 1,2,3,4 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 4 OXO 1,3 DIPHENYL 6 [(2 PIPERIDIN 1 YLETHYL)THIO] 2 THIOXO 1,2,3,4 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 4 OXO 1,3 DIPHENYL 6 [(2 PYRROLIDIN 1 YLETHYL)THIO] 2 THIOXO 1,2,3,4 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 6 [(2 DIETHYLAMINOETHYL)THIO] 4 OXO 1,3 DIPHENYL 2 THIOXO 1,2,3,4 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 6 [(2 DIISOPROPYLAMINOETHYL)THIO] 4 OXO 1,3 DIPHENYL 2 THIOXO 1,2,3,4 TETRAHYDROPYRIMIDIN 5 CARBOXYLATE; ETHYL 6 [(2 DIMETHYLAMINOETHYL)THIO] 4 OXO 1,3 DIPHENYL 2 THIOXO 1,2,3,4 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 6 [(2 MORPHOLIN 4 YLETHYL)THIO] 4 OXO 1,3 DIPHENYL 2 THIOXO 1,2,3,4 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 6 [(3 DIMETHYLAMINOPROPYL)THIO] 4 OXO 1,3 DIPHENYL 2 THIOXO 1,2,3,4 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; MERBARONE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CANCER CELL; CANCER CELL CULTURE; CATALYSIS; CELL CLONE; CELL STRAIN KB; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG CONFORMATION; DRUG POTENCY; DRUG SYNTHESIS; DRUG TOLERABILITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; LEUKEMIA CELL; MULTIDRUG RESISTANCE; PHARMACOPHORE; PHENOTYPE; PROSTATE CANCER; PROTEIN EXPRESSION; SOLID TUMOR; STRUCTURE ACTIVITY RELATION;

EID: 12444258359     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00158-5     Document Type: Article

References (51)

1. Andersen A.H., Svejstrup J.Q., Westergaard O. Adv. Pharmacol. 29:1994;83.
2. Watt P.M., Hickson I.D. Biochem. J. 303:1994;681.
3. Froelich-Ammon S.J., Osheroff N. J. Biol. Chem. 270:1995;21429.
4. Wang H.-K., Morris-Natschke S.L., Lee K.-H. Med. Res. Rev. 17:1997;367.
5. Anderson R.D., Berger N.A. Mutat. Res. 309:1994;109.
6. Sorensen B.S., Sinding J., Andersen A.H., Alsner J., Jensen P.B., Westergaard O. J. Mol. Biol. 228:1992;778.
7. Robinson M.J., Martin B.A., Gootz T.D., McGuirk P.R., Moynihan M., Sutcliffe J.A., Osheroff N. J. Biol. Chem. 266:1991;14585.
8. Madden K.R., Champoux J.J. Cancer Res. 52:1992;525.
9. Heck M.M., Earnshaw W.C. J. Cell. Biol. 103:1986;2569.
10. Sinha B.K. Drugs. 49:1995;11.
11. Nitiss J.L., Liu Y.X., Hsiung Y. Cancer Res. 53:1993;89.
12. Drake F.H., Hofmann G.A., Mong S.M., Bartus J.O., Hertzberg R.P., Johnson R.K., Mattern M.R., Mirabelli C.K. Cancer Res. 49:1989;2578.
13. Boritzki T.J., Wolfard T.S., Besser J.A., Jackson R.C., Fry D.W. Biochem. Pharmacol. 37:1988;4063.
14. Jensen P.B., Sorensen B.S., Sehsted M., Demant E.J., Kjeldsen E., Friche E., Hansen H.H. Biochem. Pharmacol. 45:1993;2025.
15. Ishida R., Miki T., Narita T., Yui R., Sato M., Utsumi K.R., Tanabe K., Andoh T. Cancer Res. 51:1991;4909.
16. Roca J., Ishida R., Berger J.M., Andoh T., Wang J.C. Proc. Natl. Acad. Sci. U.S.A. 91:1994;1781.
17. Fattman C.L., Allan W.P., Hasinoff B.B., Yalowich J.C. Biochem. Pharmacol. 52:1996;635.
18. Fortune J.M., Osheroff N. J. Biol. Chem. 273:1998;17643.
19. Chen M., Beck W.T. Cancer Res. 55:1995;1509.
20. Khelifa T., Beck W.T. Mol. Pharmacol. 55:1999;548.
21. Mo Y.Y., Beck W.T. Mol. Pharmacol. 55:1999;216.
22. Brewer A.D., Minatelli J.A., Plowmann J., Paull K.D., Narayanan W.L. Biochem. Pharmacol. 34:1985;2047.
23. Dimaggio J.J., Warrel R.P., Muindi J., Stevens Y.W., Lee S.J., Lowenthal D.A., Haines I., Walsh T.D., Baltzer L., Yaldaei S. Cancer Res. 50:1990;1151.
24. Kraut E.H., Fleming T., Macdonald J.S., Spiridonidis C.H., Bradof J.E., Baker L.H. Am. J. Clin. Oncol. 16:1993;327.
25. Ajani J.A., Winn R., Baez L., Pollock T., Maher T., Hallinan-Fueger B., Newman J. Cancer Invest. 12:1994;488.
26. Malik U.R., Dutcher J.P., Caliendo G., Lasala P., Mitnick R., Wiernik P.H. Med. Oncol. 14:1997;159.
27. Dlugosz A., Macon Z. Pharmazie. 50:1995;529.
28. Ranise A., Bruno O., Bondavalli F., Schenone S., D'Amico M., Falciani M., Filippelli W., Rossi F. ll Farmaco. 49:1994;551.
29. Krapcho A.P., Petry M.E.Z., Getahun Z., Landi J.J., Stallman J., Polsenbcrg J.F., Gallagher C.E., Maresh M.J., Hacker M.P., Giuliani F.G., Beggolin G., Pezzoni G., Menta E., Manzotti C., Oliva A., Spinelli S., Tognella S. J. Med. Chem. 37:1994;828.
30. Antonini I., Polucci P., Jenkins T.C., Kelland L.R., Menta E., Pescalli N., Stefanska B., Mazerski J., Martelli S. J. Med. Chem. 40:1997;3749.
31. Bernier J.-L., Hénichart J.-P., Warin V., Trentesaux C., Jardillier J.-C. J. Med. Chem. 28:1995;497.
32. Terada T., Fujimoto K., Nomura M., Yamashita J., Wierzba R.Y., Shibata J., Sugimoto Y., Yamada Y., Kobunai T., Takeda S., Minami Y., Yoshida K., Yamaguchi H. J. Med. Chem. 36:1993;1689.
33. Devray R., Juravj J., Fernandez J.A., Barrett J.F., Cushman M. Anticancer Drug Res. 11:1996;311.
34. Haldane A., Holdaway K.M., Finlay G.J., Baguley B.C. Cancer Chemother. Pharmacol. 32:1993;463.
35. Wang H.-K., Liu S.-Y., Hwang K.-M., Taylor G., Lee K.-H. Bioorg. Med. Chem. 2:1994;1397.
36. Bellamy, L. J. Associated XH Frequencies, The Hydrogen Bond. In Advances in Infrared Group Frequencies; Chapman and Hall: London, 1975; p 264.
37. Gompper R., Toepfl W. Chem. Ber. 95:1962;2871.
38. Tominaga Y., Honkawa Y., Hara M., Hosomi A. J. Heterocyclic Chem. 27:1990;775.
39. Monks A., Scudiero D., Skehan P., Shoemaker R., Paull K., Vistica D., Hose C., Langley J., Cronise P., Vaigro-Woiff A., Gray-Goodrich M., Campbell H., Mayo J., Boyd M. J. Natl. Cancer Inst. 83:1991;757.
40. Grever M.R., Schepartz S.A., Chabner B.A. Sem. Oncol. 19:1992;622.
41. Endicott J.A., Ling V. Ann. Rev. Biochem. 58:1989;137.
42. Twentyman P.R. Drug News Persp. 6:1993;647.
43. Chen M., Beck W.T. Cancer Res. 53:1993;5946.
44. Pastan I., Gottesman M.M., Ueda K., Lovelace E., Rutherford A.V., Willngham M.C. Proc. Natl. Acad. Sci. U.S.A. 85:1988;4486.
45. Chen H.X., Bamberger U., Heckel A., Guo X., Cheng Y.C. Cancer Res. 53:1993;1974.
46. Gaj C.L., Anyanwutaku I., Chang Y.H., Cheng Y.C. Biochem. Pharmacol. 55:1998;1199.
47. Beidler D.R., Chang J.Y., Zhou B.S., Cheng Y.C. Cancer Res. 56:1996;345.
48. Minderman H., Wrzosek C., Cao S., Utsugi T., Kobunai T., Yamada Y., Rustum Y.M. Cancer Chemother. Pharmacol. 45:2000;78.
49. Mai A., Artico M., Sbardella G., Quartarone S., Massa S., Loi A.G., De Montis A., Scintu F., Putzolu M., La Colla P. J. Med. Chem. 40:1997;1447.
50. Pauwels R., Balzarini J., Baba M., Snoeck R., Scholds D., Herdewijn P., Desmyter J., De Clercq E. J. Virol. Methods. 20:1988;309.
51. Denizot F., Lang R. J. Immunol. Methods. 89:1986;271.