2-Arylpaullones are selective antitrypanosomal agents

European Journal of Medicinal Chemistry

Volumn 64, Issue , 2013, Pages 396-400

  Ryczak, Jasmin ^a   Papini, Ma'ayan ^b   Lader, Annette ^a   Nasereddin, Abedelmajeed ^b   Kopelyanskiy, Dmitry ^b   Preu, Lutz ^a   Jaffe, Charles L ^b   Kunick, Conrad ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b HEBREW UNIVERSITY   (Israel)

Author keywords

Neglected tropical diseases; Paullones; Suzuki reaction; Trypanosoma brucei rhodesiense; Trypanosomiasis

Indexed keywords

9 TERT BUTYL 2 (4 MORPHOLINOPHENYL)PAULLONE; ACRYLAMIDE; ANTITRYPANOSOMAL AGENT; PAULLONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; HUMAN; HUMAN CELL; NONHUMAN; STRUCTURE ACTIVITY RELATION;

BENZAZEPINES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; MOLECULAR STRUCTURE; PARASITIC SENSITIVITY TESTS; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOCIDAL AGENTS; TRYPANOSOMA BRUCEI RHODESIENSE;

EID: 84877028315     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.03.065     Document Type: Article

References (24)

1. J.C. Dujardin, D. González-Pacanowska, S.L. Croft, O.F. Olesen, and G.F. Späth Collaborative actions in anti-trypanosomatid chemotherapy with partners from disease endemic areas Trends Parasitol. 26 2010 395 403
2. R.T. Jacobs, B. Nare, and M.A. Phillips State of the art in African trypanosome drug discovery Curr. Top. Med. Chem. 11 2011 1255 1274
3. S.R. Wilkinson, and J.M. Kelly Trypanocidal drugs: mechanisms, resistance and new targets Expert Rev. Mol. Med. 11 2009 e31
4. C. Reichwald, O. Shimony, U. Dunkel, N. Sacerdoti-Sierra, C.L. Jaffe, and C. Kunick 2-(3-Aryl-3-oxopropen-1-yl)-9-tert-butyl-paullones: a new antileishmanial chemotype J. Med. Chem. 51 2008 659 665 (Pubitemid 351252294)
5. P. Boeck, C. Bandeira Falcao, P. Leal, R. Yunes, V. Filho, E. Torres-Santos, and B. Rossi-Bergmann Synthesis of chalcone analogues with increased antileishmanial activity Bioorg. Med. Chem. 14 2006 1538 1545 (Pubitemid 43120289)
6. C. Gutteridge, J. Vo, C. Tillett, J. Vigilante, J. Dettmer, S. Patterson, K. Werbovetz, J. Capers, D. Nichols, A. Bhattacharjee, and L. Gerena Antileishmanial and antimalarial chalcones: synthesis, efficacy and cytotoxicity of pyridinyl and naphthalenyl analogs Med. Chem. 3 2007 115 119 (Pubitemid 47454876)
7. M. Liu, P. Wilairat, S. Croft, A.L.-C. Tan, and M.-L. Go Structure-activity relationships of antileishmanial and antimalarial chalcones Bioorg. Med. Chem. 11 2003 2729 2738 (Pubitemid 36682997)
8. S. Nielsen, S. Christensen, G. Cruciani, A. Kharazmi, and T. Liljefors Antileishmanial chalcones: statistical design, synthesis, and three-dimensional quantitative structure-activity relationship analysis J. Med. Chem. 41 1998 4819 4832 (Pubitemid 28530457)
9. C. Reichwald, O. Shimony, N. Sacerdoti-Sierra, C.L. Jaffe, and C. Kunick A new Heck reaction modification using ketone Mannich bases as enone precursors: parallel synthesis of anti-leishmanial chalcones Bioorg. Med. Chem. Lett. 18 2008 1985 1989 (Pubitemid 351380881)
10. C. Schultz, A. Link, M. Leost, D.W. Zaharevitz, R. Gussio, E.A. Sausville, L. Meijer, and C. Kunick Paullones, a series of cyclin-dependent kinase inhibitors: synthesis, evaluation of CDK1/cyclin B inhibition, and in vitro antitumor activity J. Med. Chem. 42 1999 2909 2919 (Pubitemid 29370435)
11. X. Xie, T. Lemcke, R. Gussio, D.W. Zaharevitz, M. Leost, L. Meijer, and C. Kunick Epoxide-containing side chains enhance antiproliferative activity of paullones Eur. J. Med. Chem. 40 2005 655 661 (Pubitemid 40797561)
12. Y.K. Koleva, J.C. Madden, and M.T. Cronin Formation of categories from structure-activity relationships to allow read-across for risk assessment: toxicity of alpha, beta-unsaturated carbonyl compounds Chem. Res. Toxicol. 21 2008 2300 2312
13. A. Pérez-Garrido, A.M. Helguera, G.C. López, M.N. Cordeiro, and A.G. Escudero A topological substructural molecular design approach for predicting mutagenesis end-points of alpha,beta-unsaturated carbonyl compounds Toxicology 268 2010 64 77
14. J.A. Schwöbel, D. Wondrousch, Y.K. Koleva, J.C. Madden, M.T. Cronin, and G. Schüürmann Prediction of Michael-type acceptor reactivity toward glutathione Chem. Res. Toxicol. 23 2010 1576 1585
15. J.F. Spicer, and S.M. Rudman EGFR inhibitors in non-small cell lung cancer (NSCLC): the emerging role of the dual irreversible EGFR/HER2 inhibitor BIBW 2992 Target. Oncol. 5 2010 245 255
16. A. Ocaña, and E. Amir Irreversible pan-ErbB tyrosine kinase inhibitors and breast cancer: current status and future directions Cancer Treat. Rev. 35 2009 685 691
17. E.L. Kwak, R. Sordella, D.W. Bell, N. Godin-Heymann, R.A. Okimoto, B.W. Brannigan, P.L. Harris, D.R. Driscoll, P. Fidias, T.J. Lynch, S.K. Rabindran, J.P. McGinnis, A. Wissner, S.V. Sharma, K.J. Isselbacher, J. Settleman, and D.A. Haber Irreversible inhibitors of the EGF receptor may circumvent acquired resistance to gefitinib Proc. Natl. Acad. Sci. U.S.A. 102 2005 7665 7670 (Pubitemid 40741028)
18. G.P. Sagitullina, M.A. Vorontsova, A.K. Garkushenko, N.V. Poendaev, and R.S. Sagitullin Nitropyridines: X. Palladium-catalyzed cross-coupling of 2-bromo-5-nitropyridine with terminal acetylenes Russ. J. Org. Chem. 46 2010 1830 1834
19. A.-M. Egert-Schmidt, J. Dreher, U. Dunkel, S. Kohfeld, L. Preu, H. Weber, J.E. Ehlert, B. Mutschler, F. Totzke, C. Schächtele, M.H.G. Kubbutat, K. Baumann, and C. Kunick Identification of 2-anilino-9-methoxy-5,7-dihydro-6H- pyrimido[5,4-d][1]benzazepin-6-ones as dual PLK1/VEGF-R2 kinase inhibitor chemotypes by structure-based lead generation J. Med. Chem. 53 2010 2433 2442
20. J. Eriksson, O. Åberg, and B. Långström Synthesis of [11C]/[13C]acrylamides by palladium-mediated carbonylation Eur. J. Org. Chem. 2007 2007 455 461
21. C. Le Sann, J. Huddleston, and J. Mann Synthesis and preliminary evaluation of novel analogues of quindolines as potential stabilisers of telomeric G-quadruplex DNA Tetrahedron 63 2007 12903 12911 (Pubitemid 350116222)
22. N. Kuhnert, and A. Le-Gresley Synthesis and capsule formation of upper rim substituted tetra-acrylamido calix[4]arenes Org. Biomol. Chem. 3 2005 2175 2182 (Pubitemid 40859897)
23. E. Chatelain, and J.-R. Ioset Drug discovery and development for neglected diseases: the DNDi model Drug Des. Dev. Ther. 5 2011 175 181
24. B. Räz, M. Iten, Y. Grether-Bühler, R. Kaminsky, and R. Brun The Alamar Blue assay to determine drug sensitivity of African trypanosomes (T.b. rhodesiense and T.b. gambiense) in vitro Acta Trop. 68 1997 139 147 (Pubitemid 27438330)