Synthesis and biological evaluation of cis-locked vinylogous combretastatin-A4 analogues: Derivatives with a cyclopropyl-vinyl or a cyclopropyl-amide bridge

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 5, 2009, Pages 1318-1322

  Ty, Nancy ^a,b   Kaffy, Julia ^a,b   Arrault, Alban ^c,d   Thoret, Sylviane ^b   Pontikis, Renée ^a,b   Dubois, Joelle ^b   Morin Allory, Luc ^c,d   Florent, Jean Claude ^a,b  

^a INSTITUT CURIE   (France)

^b CNRS   (France)

^c UNIVERSITÉ D'ORLÉANS   (France)

^d Université d'Orléans   (France)

Author keywords

Bioisosteric replacement; Colchicine binding site; Combretastatin A4; Cyclopropane; Tubulin polymerization

Indexed keywords

ANTINEOPLASTIC AGENT; COMBRETASTATIN A4 DERIVATIVE; CYCLOPROPANE DERIVATIVE; LIGAND; TUBULIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG BINDING SITE; DRUG SCREENING; DRUG SYNTHESIS; ENANTIOMER; MICROTUBULE ASSEMBLY; STRUCTURE ACTIVITY RELATION;

AMIDES; BINDING SITES; CELL LINE, TUMOR; CYCLOPROPANES; DRUG EVALUATION, PRECLINICAL; HUMANS; PROTEIN BINDING; STILBENES; TUBULIN; VINYL COMPOUNDS;

EID: 60449107894     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.01.062     Document Type: Article

References (44)

1. Denekamp J. Int. J. Radiation Biol. 60 (1991) 401
2. Arap W., Pasqualini R., and Ruoslahti E. Curr. Opin. Oncology 10 (1998) 560
3. Pasquier E., André N., and Braguer D. Curr. Cancer Drug Targets 7 (2007) 566
4. Patterson D.M., and Rustin G.J.S. Clin. Oncol. 19 (2007) 443
5. Lippert III J.W. Bioorg. Med. Chem. 15 (2007) 605
6. Hinnen P., and Eskens F.A.L.M. Br. J. Cancer 96 (2007) 1159
7. Cai S.X. Recent Patents Anticancer Drug Discov. 2 (2007) 79
8. West C.M.L., and Price P. Anti-cancer Drugs 15 (2004) 179
9. Horsman M.R., and Siemann D.W. Cancer Res. 66 (2006) 11520
10. Pettit G.R., Singh S.B., Hamel E., Lin C.M., Alberts D.S., and Garcia-Kendall D. Experientia 45 (1989) 209
11. Kanthou C., and Tozer G.M. Blood 99 (2002) 2060
12. Vincent L., Kermani P., Young L.M., Cheng J., Zhang F., Shido K., Lam G., Bompais-Vincent H., Zhu Z., Hicklin D.J., Bohlen P., Chaplin D.J., May C., and Rafi S. J. Clin. Invest. 115 (2005) 2992
13. 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
14. Tozer G.M., Kanthou C., and Baguley B.C. Nat. Rev. Cancer 5 (2005) 423 and references cited therein
15. For reviews on CA4 analogues see. Nam N.-H. Curr. Med. Chem. 10 (2003) 1697
16. Hsieh H.P., Liou J.P., and Mahindroo N. Curr. Pharm. Design 11 (2005) 1655
17. Tron G.C., Pirali T., Sorba G., Pagliai F., Busacca S., and Genazzani A. J. Med. Chem. 49 (2006) 3033
18. Lawrence N.J., Patterson R.P., Ooi L.-L., Cook D., and Ducki S. Bioorg. Med. Chem. Lett. 16 (2006) 5844
19. Romagnoli R., Baraldi P.G., Carrion M.D., Lopez Cara C., Cruz-Lopez O., Preti D., Tolomeo M., Grimaudo S., Di Cristina A., Zonta N., Balzarini J., Brancale A., Sarkar T., and Hamel E. Bioorg. Med. Chem. 16 (2008) 5367
20. Provot O., Giraud A., Peyrat J.-F., Alami M., and Brion J.-D. Tetrahedron Lett. 46 (2005) 8547
21. Kaffy J., Pontikis R., Florent J.C., and Monneret C. Org. Biomol. Chem. 3 (2005) 2657
22. See, for example. Lagu B., Lebedev R., Pio B., Yang M., and Pelton P. Bioorg. Med. Chem. Lett. 17 (2007) 3491
23. Carpita A., Ribecai A., Rossi R., and Stabile P. Tetrahedron 58 (2002) 3673
24. Cis or trans refer to the cyclopropane ring stereochemistry, E or Z to the olefinic bond configuration. All the synthesized cyclopropyl derivatives are cis or trans racemates.
25. Konno K., Ojima K., Hayashi T., Tanabe M., and Takayama H. Chem. Pharm. Bull. 45 (1997) 185
26. Kato M., Kido F., Wu M.-D., and Yoshikoshi A. Bull. Chem. Soc. Jpn 47 (1974) 1516
27. Cooper P.D. Can. J. Chem. 48 (1970) 3882
28. 1H NMR values for the aldehyde proton allowed easy attribution of the cis or trans stereochemistry for the cyclopropane ring (δ = 8.66 ppm, J = 6.9 Hz/δ = 9.33 ppm, J = 4.6 Hz, respectively).
29. Yamaguchi K., Kazuta Y., Abe H., Matsuda A., and Shuto S. J. Org. Chem. 68 (2003) 9255
30. 1H NMR chemical shifts analysis. For derivatives 3a and 9a with a cis-cyclopropane unit, the cyclopropyl protons H-a and H-c resonate at lower field than in the trans-compounds (∼0.35 and 0.20 ppm, respectively), while the olefinic proton H-d is shielded (∼0.35 ppm). For atom numbering see Scheme 1.
31. +) 311.1647, found 311.1643.
32. Ramacciotti A., Fiaschi R., and Napolitano E. Tetrahedron: Asymmetry 7 (1996) 1101
33. Doyle M.P. Chem. Rev. 86 (1986) 919
34. Majchrzak M.W., and Kotelko A. Synthesis 6 (1983) 469
35. ac (9.4 and 9.2) is consistent with a cis-disposition of the substituents on the cyclopropyl ring.
36. Hennessy E.J., and Buchwald S.L. J. Am. Chem. Soc. 125 (2003) 12084
37. Watanabe T., Suzuki T., Umezawa Y., Takeuchi T., Otsuka M., and Umezawa K. Tetrahedron 56 (2000) 741
38. 1H NMR spectra of the cis-cyclopropyl-amide compounds show a downfield shift (approximately 0.30-0.35 ppm) of the H-c protons relative to the same protons of the trans-isomers.
39. Hadfield J.A., Gaukroger K., Hirst N., Weston A.P., Lawrence N.J., and McGown A.T. Eur. J. Med. Chem. 40 (2005) 529
40. Hadimani M.B., Hua J., Jonklaas M.D., Kessler R.J., Sheng Y., Olivares A., Tanpure R.P., Weiser A., Zhang J., Edvarsen K., Kane R.R., and Pinney K.G. Bioorg. Med. Chem. Lett. 13 (2003) 1505
41. Ravelli R.B., Gigant B., Curmi P.A., Jourdain I., Lachkar S., Sobel A., and Knossow M. Nature 428 (2004) 198
42. Jones G., Willett P., and Glen R.C. J. Mol. Biol. 24 5 (1995) 43
43. Nguyen T.L., McGrath C., Hermone A.R., Burnett J.C., Zaharevitz D.W., Day B.W., Wipf P., Hamel E., and Gussio R. J. Med. Chem. 48 (2005) 6107
44. Such cavity had already been reported. See, for example. Bellina F., Cauteruccio S., Monti S., and Rossi R. Bioorg. Med. Chem. Lett. 16 (2006) 5757