Synthesis and antitumor-evaluation of cyclopropyl-containing combretastatin analogs

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 24, 2009, Pages 6948-6951

  Fürst, Rita ^a   Zupkó, István ^b   Berényi, Ágnes ^b   Ecker, Gerhard F ^a   Rinner, Uwe ^a  

^a UNIVERSITY OF VIENNA   (Austria)

^b UNIVERSITY OF SZEGED   (Hungary)

Author keywords

Anticancer drug; Colchicine; Combretastatin; Stilbene; Tubulin binding

Indexed keywords

ANTINEOPLASTIC AGENT; COMBRETASTATIN; COMBRETASTATIN A4 PHOSPHATE; CYCLOPROPANE DERIVATIVE; SERINE 2 METHOXY 5 [2 (3,4,5 TRIMETHOXYPHENYL)VINYL]ANILIDE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOLECULAR DOCKING; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CYCLOPROPANES; HUMANS; STILBENES; TUBULIN MODULATORS;

EID: 71849087235     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.10.064     Document Type: Article

References (32)

1. Pettit G.R., Cragg G.M., Herald D.L., Schmidt J.M., and Lohavanijaya P. Can. J. Chem. 60 (1982) 1374
2. Lin C.M., Ho H.H., Pettit G.R., and Hamel E. Biochemistry 28 (1989) 6984
3. Cirla A., and Mann J. J. Nat. Prod. Rep. 20 (2003) 558
4. Cushman M., Nagarathnam D., Gopal D., He H.M., Lin C.M., and Hamel E. J. Med. Chem. 35 (1992) 2293
5. Chaudhary A., Pandeya S.N., Kumar P., Sharma P., Gupta S., Soni N., Verma K.K., and Bhardwaj G. Mini-Rev. Med. Chem. 7 (2007) 1186
6. Brown T., Holt H., and Lee M. In: Gupta R.R. (Ed). Topics in Heterocyclic Chemistry (2006), Springer, Berlin, Heidelberg 1-51
7. Hatanaka T., Fujita K., Ohsumi K., Nakagawa R., Fukuda Y., Nihei Y., Suga Y., Akiyama Y., and Tsuji T. Bioorg. Med. Chem. Lett. 8 (1998) 3371
8. Tron G.C., Pirali T., Sorba G., Pagliai F., Busacca S., and Genazzani A. J. Med. Chem. 49 (2006) 3033
9. Borrel C., Thoret S., Cachet X., Guenard D., Tillequin F., Koch M., and Michel S. Bioorg. Med. Chem. 13 (2005) 3853
10. Monk K.A., Siles R., Hadimani M.B., Mugabe B.E., Ackley J.F., Studerus S.W., Edvardsen K., Trawick M.L., Garner C.M., Rhodes M.R., Pettit G.R., and Pinney K.G. Bioorg. Med. Chem. 14 (2006) 3231
11. Lin C.M., Singh S.B., Chu P.S., Dempcy R.O., Schmidt J.M., Pettit G.R., and Hamel E. Mol. Pharmacol. 34 (1988) 200
12. Nandy P., Banerjee S., Gao H., Hui M.B.V., and Lien E.J. Pharm. Res. 8 (1991) 776
13. Hori K., Saito S., and Kubota K. Br. J. Cancer 86 (2002) 1604
14. Salmon H.W., Mladinich C., and Siemann D.W. Eur. J. Cancer 42 (2006) 3073
15. Robinson S.P., McIntyre D.J.O., Checkley D., Tessier J.J., Howe F.A., Griffiths J.R., Ashton S.E., Ryan A.J., Blakey D.C., and Waterton J.C. Br. J. Cancer 88 (2003) 1592
16. West C.M.L., and Price P. Anti-Cancer Drugs (2004) 179
17. Dowlati A., Robertson K., Cooney M., Petros W.P., Stratford M., Jesberger J., Rafie N., Overmoyer B., Makkar V., Stambler B., Taylor A., Waas J., Lewin J.S., McCrae K.R., and Remick S.C. Cancer Res. 62 (2002) 3408
18. Wang L., Woods K.W., Li Q., Barr K.J., McCroskey R.W., Hannick S.M., Gherke L., Credo R.B., Hui Y.H., Marsh K., Warner R., Lee J.Y., Zielinski-Mozng N., Frost D., Rosenberg S.H., and Sham H.L. J. Med. Chem. 45 (2002) 1697
19. Kim Y., Nam N.H., You Y.J., and Ahn B.Z. Bioorg. Med. Chem. Lett. 12 (2002) 719
20. Simoni D., Grisolia G., Giannini G., Roberti M., Rondanin R., Piccagli L., Baruchello R., Rossi M., Romagnoli R., Invidiata F.P., Grimaudo S., Jung M.K., Hamel E., Gebbia N., Crosta L., Abbadessa V., Di Cristina A., Dusonchet L., Meli M., and Tolomeo M. J. Med. Chem. 48 (2005) 723
21. Jonnalagadda S.S., terHaar E., Hamel E., Lin C.M., Magarian R.A., and Day B.W. Bioorg. Med. Chem. 5 (1997) 715
22. van de Sande M., and Gais H.J. Chem.-Eur. J. 13 (2007) 1784
23. Castanet A.S., Colobert F., and Schlama T. Org. Lett. 2 (2000) 3559
24. Bui V.P., Hudlicky T., Hansen T.V., and Stenstrom Y. Tetrahedron Lett. 43 (2002) 2839
25. Pettit G.R., Minardi M.D., Rosenberg H.J., Hamel E., Bibby M.C., Martin S.W., Jung M.K., Pettit R.K., Cuthbertson T.J., and Chapuis J.C. J. Nat. Prod. 68 (2005) 1450
26. Li H.B., Yang H., Petersen J.L., and Wang K.K. J. Org. Chem. 69 (2004) 4500
27. Mosmann T. J. Immunol. Methods 65 (1983) 55
28. Hadfield J.A., and McGown A.T. Synth. Commun. 28 (1998) 1421
29. Lin C.M., Singh S.B., Chu P.S., Dempcy R.O., Schmidt J.M., Pettit G.R., and Hamel E. Mol. Pharmacol. 34 (1988) 200
30. Pettit G.R., Minardi M.D., Rosenberg H.J., Hamel E., Bibby M.C., Martin S.W., Jung M.K., Pettit R.K., Cuthbertson T.J., and Chapuis J.C. J. Nat. Prod. 68 (2005) 1450
31. Ravelli R.B.G., Gigant B., Curmi P.A., Jourdin I., Lachkar S., Sobel A., and Knossow M. Nature 428 (2004) 198
32. Docking was performed with the software package moe version 2008.10 (Chemical Computing Group). All amino acids in a distance of 4.5 Å to colchicine were used for defining the receptor. Ligands were docked using the Triangle Matcher as placement routine with the rotate bonds function activated. Rescoring 1 was performed with London dG, GridMin was used for refinement and Affinity dG was selected for rescoring 2. The top 10 ranked poses for each ligand were analyzed.