The synthesis and anticancer activity of analogs of the indole phytoalexins brassinin, 1-methoxyspirobrassinol methyl ether and cyclobrassinin This work is dedicated to the memory of Associated Professor Peter Kutschy (1953-2012)

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 21, 2013, Pages 6623-6633

  Budovská, Mariana ^a   Pilátová, Martina ^a   Varinská, Lenka ^a   Mojžiš, Ján ^a   Mezencev, Roman ^b  

^a P J AFÁRIK UNIVERSITY   (Slovakia)

^b Georgia Institute of Technology   (United States)

Author keywords

Antiproliferative activity; Cyclobrassinin; Indoles; Phytoalexins; Spirocyclization

Indexed keywords

1 (TERT BUTOXYCARBONYL) 2 HYDROXY 2' (PHENYLAMINO)SPIRO(INDOLINE 3,5' [4',5'] DIHYDROTHIAZOLE); 1 (TERT BUTOXYCARBONYL) 2 METHOXY 2' (PHENYLAMINO)SPIRO(INDOLINE 3,5' [4',5']DIHYDROTHIAZOLE); 1 METHOXYSPIROBRASSINOL METHYL ETHER DERIVATIVE; 2 PHENYLAMINO 4H 1,3 THIAZINO[6,5 B]INDOL; BRASSININ DERIVATIVE; CISPLATIN; COMBRETASTATIN A4; CYCLOBRASSININ DERIVATIVE; DOXORUBICIN; ETOPOSIDE; INDOLE DERIVATIVE; N [1 (TERT BUTOXYCARBONYL)INDOL 3 YL]METHYL N' METHYL N' PHENYLTHIOUREA; N [1 (TERT BUTOXYCARBONYL)INDOL 3 YL]METHYL N' PHENYLTHIOUREA; PACLITAXEL; PHYTOALEXIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONTROLLED STUDY; DEPROTECTION REACTION; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ELIMINATION REACTION; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; HUMAN; HUMAN CELL; LEUKEMIA CELL LINE; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SOLID TUMOR; SPIROCYCLIZATION; UMBILICAL VEIN ENDOTHELIAL CELL;

ANTIPROLIFERATIVE ACTIVITY; CYCLOBRASSININ; INDOLES; PHYTOALEXINS; SPIROCYCLIZATION;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; DRUG SCREENING ASSAYS, ANTITUMOR; HELA CELLS; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; HUMANS; INDOLES; JURKAT CELLS; MAGNETIC RESONANCE SPECTROSCOPY; MCF-7 CELLS; SESQUITERPENES; STEREOISOMERISM; THIOCARBAMATES;

EID: 84885181459     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.08.020     Document Type: Article

References (29)

1. R.P. Purkayastha Progress in Phytoalexin Research During the Past 50 years M. Daniel, R.P. Purkayastha, Handbook of Phytoalexin Metabolism and Action 1995 Marcel Dekker New York 1 39
2. M.S.C. Pedras, E.E. Yaya, and E. Glawischnig Nat. Prod. Rep. 28 2011 1381
3. M.S.C. Pedras, Q. Zheng, and V.K. Sarma-Mamillapale Nat. Prod. Commun. 2 2007 319
4. M. Takasugi, K. Monde, N. Katsui, and A. Shirata Bull. Chem. Soc. Jpn. 61 1988 285
5. R.G. Mehta, J. Liu, A. Constantinou, C.F. Thomas, A. Hawthorne, M. You, C. Gerhäuser, J.M. Pezzuto, R.C. Moon, and R.M. Moriarty Carcinogenesis 16 1995 399
6. P. Kutschy, M. Suchý, K. Monde, N. Harada, R. Maruš ková, Z. Čurillová, M. Dzurilla, M. Miklošová , R. Mezencev, and J. Mojžiš Tetrahedron Lett. 43 2002 9489
7. P. Csomós, L. Fodor, P. Sohár, and G. Bernáth Tetrahedron 61 2005 9257
8. P. Csomós, I. Zupkó, B. Réthy, L. Fodor, G. Falkay, and G. Bernáth Bioorg. Med. Chem. 16 2006 6273
9. R. Mezencev, P. Kutschy, A. Salayová, Z. Čurillová, J. Mojžiš, M. Pilátová, and J. McDonald Chemotherapy 54 2008 372
10. R. Mezencev, P. Kutschy, A. Salayová, T. Updegrove, and J.F. McDonald Neoplasma 56 2009 321
11. P. Kutschy, A. Salayová, Z. Čurillová, T. Kožár, R. Mezencev, J. Mojžiš, M. Pilátová, E. Balentová, P. Pazdera, M. Sabol, and M. Zburová Bioorg. Med. Chem. 17 2009 3698
12. R. Mezencev, M. Galizzi, P. Kutschy, and R. Docampo Exp. Parasitol. 122 2009 66
13. R. Mezencev, J. Mojžiš, M. Pilátová, and P. Kutschy Neoplasma 50 2003 239
14. P. Kutschy, and R. Mezencev Indole Phytoalexins from Brassicaceae: Synthesis and Anticancer Activity O.A. Attanasi, D. Spinelli, Targets in Heterocyclic Systems Chemistry and Properties Vol. 12 2009 Italian Society of Chemistry Urbino, Italy 120 148 ISBN: 978-88-86208-56-7, ISSN: 1724-9449
15. M. Sabol, P. Kutschy, L. Siegfried, A. Miroššay, M. Suchý, H. Hrbková, M. Dzurilla, R. Marušková, J. Starková, and E. Paulíková Biologia 55 2000 701
16. R.G. Mehta, J. Liu, A. Constantinou, M. Hawthorne, J.M. Pezzuto, R.C. Moon, and R.M. Moriarty Anticancer Res. 14 1994 1209
17. P. Gaspari, T. Banerjee, W.P. Malachowski, A.J. Muller, J.D. Prendergast, J. DuHadaway, S. Bennett, and A.M. Donovan J. Med. Chem. 49 2006 684
18. T. Banerjee, J.B. Duhadaway, P. Gaspari, E. Sutanto-Ward, D.H. Munn, A.L. Mellor, W.P. Malachowski, G.C. Prendergast, and A.J. Muller Oncogene 27 2008 2851
19. C. Tempete, M. Devys, and M. Barbier Z. Naturforsch. 46 1991 706
20. K. Monde, T. Taniguchi, N. Miura, P. Kutschy, Z. Čurillová, M. Pilátová, and J. Mojžiš Bioorg. Med. Chem. 13 2005 5206
21. P. Kutschy, M. Dzurilla, M. Takasugi, M. Török, I. Achbergerová, R. Homzová, and M. Rácová Tetrahedron 54 1998 3549
22. M. Budovská, P. Kutschy, T. Kožár, T. Gondová, and J. Petrovaj Tetrahedron 69 2013 1092
23. K. Monde, M. Takasugi, and A. Shirata Phytochemistry 39 1995 581
24. Budovská, M.; Kutschy, P.; Čurillová, Z. Diastereoselectivity of spirocyclization of 1-methoxy and 1-acyl derivatives of indole phytoalexin brassinin. Unpublished results.
25. G. La Regina, T. Sarkar, R. Bai, M.C. Edler, R. Saletti, A. Coluccia, F. Piscitelli, L. Minelli, V. Gatti, C. Mazzoccoli, V. Palermo, C. Mazzoni, C. Falcone, A.I. Scovassi, V. Giansanti, P. Campiglia, A. Porta, B. Maresca, E. Hamel, A. Brancale, E. Novellino, and R. Silvestri J. Med. Chem. 52 2009 7512
26. P. Defilippi, V.W.M. van Hinsbergh, A. Bertolotto, P. Rossino, L. Silengo, and G. Tarone J. Cell Biol. 114 1991 855
27. V.W. van Hinsbergh, E.D. Sprengers, and E.A. Kooistra Thromb. Haemost. 57 1987 148
28. T. Mosmann J. Immunol. Methods 65 1983 55
29. G.J. Kaspers, A.J. Veerman, R. Pieters, G.J. Broekema, D.R. Huismans, K.M. Kazemier, A.H. Loonen, M.A. Rottier, C.H. van Zantwijk, K. Hählen, and E.R. van Wering Br. J. Cancer 70 1994 1047