Synthesis and biological evaluation of new disubstituted analogues of 6-methoxy-3-(3′,4′,5′-trimethoxybenzoyl)-1H-indole (BPR0L075), as potential antivascular agents

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 15, 2008, Pages 7494-7503

  Ty, Nancy ^a   Dupeyre, Grégory ^a   Chabot, Guy G ^a   Seguin, Johanne ^a   Tillequin, François ^a   Scherman, Daniel ^a   Michel, Sylvie ^a   Cachet, Xavier ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Antivascular agents; B16 melanoma cells; BPR0L075; Combretastatin A4; Cytotoxicity; Disubstituted 3 aroylindoles; EA.hy 926 endothelial cells; Tubulin polymerization

Indexed keywords

5 HYDROXY 6 METHOXY 3 (3',4',5' TRIMETHOXYBENZOYL) 1H INDOLE; 5 METHANESULFONYLOXY 6 METHOXY 3 (3',4',5' TRIMETHOXYBENZOYL) 1H INDOLE; 5 METHANESULFONYLOXY 6 METHOXY N PHENYLSULFONYL 3 (3',4',5' TRIMETHOXYBENZOYL) 1H INDOLE; 6 HYDROXY 5 METHOXY 3 (3',4',5' TRIMETHOXYBENZOYL) 1H INDOLE; 6 METHANESULFONYLOXY 5 METHOXY 3 (3',4',5' TRIMETHOXYBENZOYL) 1H INDOLE; 6 METHANESULFONYLOXY 5 METHOXY N PHENYLSULFONYL 3 (3',4',5' TRIMETHOXYBENZOYL) 1H INDOLE; 6 METHANESULFONYLOXY 6 METHOXY 3 (3',4',5' TRIMETHOXYBENZOYL) 1H INDOLE; 6 METHOXY 3 (3',4',5' TRIMETHOXYBENZOYL) 1H INDOLE; 7 HYDROXY 6 METHOXY 3 (3',4',5' TRIMETHOXYBENZOYL) 1H INDOLE; BPROL 075; COMBRETASTATIN A4; INDOLE DERIVATIVE; UNCLASSIFIED DRUG; VASCULAR TARGETING AGENT;

ANIMAL CELL; ARTICLE; CELL ASSAY; CELL STRUCTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ENDOTHELIUM CELL; HUMAN; HUMAN CELL; MELANOMA B16; MICROTUBULE ASSEMBLY; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE; HUMANS; INDOLES; MICE; MOLECULAR STRUCTURE; NEOVASCULARIZATION, PATHOLOGIC; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 48449088613     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.06.002     Document Type: Article

References (57)

1. Cragg G.M., and Newman D.J. J. Nat. Prod. 67 (2004) 232
2. Beckers T., and Mahboobi S. Drugs Future 28 (2003) 767
3. Jordan M.A., and Wilson L. Nat. Rev. Cancer 4 (2004) 253
4. Tozer G.M., Kanthou C., and Baguley B.C. Nat. Rev. Cancer 5 (2005) 423
5. Miller J.C., Pien H.H., Sahani D., Sorensen A.G., and Thrall J.H. J. Natl. Cancer Inst. 97 (2005) 172
6. Kanthou C., and Tozer G.M. Expert Opin. Ther. Targets 11 (2007) 1443
7. Lippert III J.W. Bioorg. Med. Chem. 15 (2007) 605
8. Patterson D.M., and Rustin G.J. Clin. Oncol. (R. Coll. Radiol.) 19 (2007) 443
9. Temming K., and Kok R.J. Chem. Med. Chem. 2 (2007) 433
10. Hinnen P., and Eskens F. Br. J. Cancer 96 (2007) 1159
11. Cai S.X. Recent Patents Anticancer Drug Discov. 2 (2007) 79
12. Pilat M.J., and LoRusso P.M. J. Cell. Biochem. 99 (2006) 1021
13. Siemann D.W., Bibby M.C., Dark G.G., Dicker A.P., Eskens F.A., Horsman M.R., Marmé D., and LoRusso P.M. Clin. Cancer Res. 11 (2005) 416
14. Kogai T., Kanamoto Y., Che L.H., Taki K., Moatamed F., Schultz J.J., and Brent G. A. Cancer Res. 64 (2004) 415
15. Thorpe P.E., Chaplin D.J., and Blakey D.C. Cancer Res. 63 (2003) 1144
16. Griggs J., Metcalfe J.C., and Hesketh R. Lancet Oncol. 2 (2001) 82
17. Pettit G.R., Singh S.B., Hamel E., Lin C.M., Alberts D.S., and Garcia-Kendall D. Experientia 45 (1989) 209
18. Pettit G.R., Singh S.B., Boyd M.R., Hamel E., Pettit R.K., Schmidt J.M., and Hogan F. J. Med. Chem. 38 (1995) 1666
19. Reviews on CA-4. Tron G.C., Pirali T., Sorba G., Pagliai F., Busacca S., and Genazzani A.A. J. Med. Chem. 49 (2006) 3033
20. Pinney K.G., Jelinek C., Edvarsen K., Chaplin D.J., and Pettit G.R. The discovery and development of the combretastatins. In: Cragg G.M., Kingston D.G.I., and Newman D.J. (Eds). Anticancer Agents from Natural Products (2005), Brunner-Routledge Psychology Press, Taylor & Francis Group, Boca Raton, FL 23
21. Nam N. Curr. Med. Chem. 10 (2003) 1697
22. Bibby M.C. Drugs Future 27 (2002) 475
23. Cooney M.M., Ortiz J., Bukowski R.M., and Remick S.C. Curr. Oncol. Rep. 7 (2005) 90
24. Chaplin D.J., Pettit G.R., and Hill S.A. Anticancer Res. 19 (1999) 189
25. Tozer G.M., Prise V.E., Wilson J., Locke R.J., Vojnovic B., Stratford M.R.L., Dennis M.F., and Chaplin D.J. Cancer Res. 59 (1999) 1626
26. Oxigene company Web site. Phase II/III Study Assessing Zybrestat™ (Combretastatin), A Potential New Treatment for Anaplastic Thyroid Cancer. URL: www.oxigene.com, May, 2008.
27. Liou J.P., Chang Y.L., Kuo F.M., Chang C.W., Tseng H.Y., Wang C.C., Yang Y.N., Chang J.Y., Lee S.J., and Hsieh H.P. J. Med. Chem. 47 (2004) 4247
28. Dupeyre G., Chabot G.G., Thoret S., Cachet X., Seguin J., Guenard D., Tillequin F., Scherman D., Koch M., and Michel S. Bioorg. Med. Chem. 14 (2006) 4410
29. Kuo C.C., Hsieh H.P., Pan W.Y., Chen C.P., Liou J.P., Lee S.J., Chang Y.L., Chen L.T., Chen C.T., and Chang J.Y. Cancer Res. 64 (2004) 4621
30. Chang Y.W., Chen W.C., Lin K.T., Chang L., Yao H.T., Hsieh H.P., Lan S.J., Chen C.T., Chao Y.S., and Yeh T.K. J. Chromatogr. B 846 (2007) 162
31. Liou J.P., Mahindroo N., Chang C.W., Guo F.M., Lee S.W., Tan U.K., Yeh T.K., Kuo C.C., Chang Y.W., Lu P.H., Tung Y.S., Lin K.T., Chang J.Y., and Hsieh H.P. Chem. Med. Chem. 1 (2006) 1106
32. Silvestri and coworkers have recently published SAR studies of 3-arylthioindoles. SAR findings for this series, were found to be markedly different from those of 3-aroylindoles. De Martino G., La Regina G., Coluccia A., Edler M.C., Barbera M.C., Brancale A., Wilcox E., Hamel E., Artico M., and Silvestri M. J. Med. Chem. 47 (2004) 6120
33. La Regina G., Edler M.C., Brancale A., Kandil S., Coluccia A., Piscitelli F., Hamel E., De Martino G., Matesanz R., Diaz J.F., Scovassi A.I., Prosperi E., Lavecchia A., Novellino E., Artico M., and Silvestri R. J. Med. Chem. 50 (2007) 2865
34. Pinney, K.; Wang, F.; Hadimani, M.; Del Pilar Mejia, M. PCT Int. Appl. WO 099139, 2004; Chem. Abstr. 2004, 141, 424108.
35. Hadimani M.B., Kessler R.J., Kautz J.A., Ghatak A., Shirali R., O'Dell H., Garner C.M., and Pinney G. Acta Crystallogr. C58 (2002) 330
36. Pinney, K.; Wang, F.; Del Pilar Mejia, M. PCT Int. Appl. WO 019794, 2001; Chem. Abstr. 2001, 134, 237388.
37. Flynn B.L., Hamel E., and Jung M.K. J. Med. Chem. 45 (2002) 2670
38. Flynn, B. L.; Hamel, E. PCT Int. Appl. WO 060872, 2002; Chem. Abstr. 2002, 137, 154849.
39. Duan J.X., Cai X., Meng F., Lan L., Hart C., and Matteucci M. J. Med. Chem. 50 (2007) 1001
40. Edgell C.J., McDonald C.C., and Graham J.B. Proc. Natl. Acad. Sci. U.S.A. 80 (1983) 3734
41. Benigni J., and Mimis D. J. Heterocycl. Chem. 2 (1965) 387
42. See Supplementary data.
43. Sridhar M., Kumar B., and Narender R. Tetrahedron Lett. 39 (1998) 2847
44. Fukuyama Y., Iwatsuki C., and Kodama M. Tetrahedron 54 (1998) 10007
45. Perez R.A., Fernandez-Alvarez E., Nieto O., and Piedrafita F.J. J. Med. Chem. 35 (1992) 4584
46. Yang C., Patel H., Ku Y.-Y., Shah R., and Sawick D. Synth. Commun. 27 (1997) 2125
47. Galbraith S.M., Chaplin D.J., Lee F., Stratford M.R., Locke R.J., Vojnovic B., and Tozer G.M. Anticancer Res. 21 (2001) 93
48. Kanthou C., and Tozer G.M. Blood 99 (2002) 2060
49. 11
50. Holwell S.E., Cooper P.A., Thompson M.J., Pettit G.R., Lippert III L.W., Martin S.W., and Bibby M.C. Anticancer Res. 22 (2002) 3933
51. Holwell S.E., Cooper P.A., Grosios K., Lippert III J.W., Pettit G.R., Shnyder S.D., and Bibby M.C. Anticancer Res. 22 (2002) 707
52. Shelanski M.L., Gaskin F., and Cantor C.R. Proc. Natl. Acad. Sci. U.S.A. 70 (1973) 765
53. Zavala F., Guenard D., Robin J.P., and Brown E. J. Med. Chem. 23 (1980) 546
54. Gaukroger K., Hadfield J.A., Hepworth L.A., Lawrence N.J., and Mc Gown A.T. J. Org. Chem. 66 (2001) 8135
55. Scudiero D.A., Shoemaker R.H., Paull K.D., Monks A., Tierney S., Nofziger T.H., Currens M.J., Seniff D., and Boyd M.R. Cancer Res. 48 (1988) 4827
56. Bouis D., Hospers G.A., Meijer C., Molema G., and Mulder N.H. Angiogenesis 4 (2001) 91
57. DeMartino G., La Regina G., Coluccia A., Edler M.C., Barbera M.C., Brancale A., Wilcox E., Hamel E., Artico M., and Silvestri R. J. Med. Chem. 47 (2004) 6120