Synthesis of novel guttiferone A derivatives: In-vitro evaluation toward Plasmodium falciparum, Trypanosoma brucei and Leishmania donovani

European Journal of Medicinal Chemistry

Volumn 65, Issue , 2013, Pages 284-294

  Fromentin, Yann ^a   Gaboriaud Kolar, Nicolas ^a   Lenta, Bruno Ndjakou ^b   Wansi, Jean Duplex ^c   Buisson, Didier ^d   Mouray, Elisabeth ^d   Grellier, Philippe ^d   Loiseau, Philippe M ^e   Lallemand, Marie Christine ^a   Michel, Sylvie ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b UNIVERSITY OF YAOUNDÉ I   (Cameroon)

^c UNIVERSITY OF DOUALA   (Cameroon)

^d MUSÉUM NATIONAL D'HISTOIRE NATURELLE   (France)

^e CNRS   (France)

Author keywords

Antiparasitic activities; Guttiferone A derivatives; Natural products; Semi synthesis; Substitution on the catechol ring

Indexed keywords

13 O ACETYL GUTTIFERONE A; 13,14 BIS O 2 ETHYL 1,3 DIOXOLANE GUTTIFERONE A; 13,14 BIS O 2 METHOXY 5 NITROBENZYL GUTTIFERONE A; 13,14 BIS O 3,3 DIMETHYLACRYLOYLATE GUTTIFERONE A; 13,14 BIS O ACETYL GUTTIFERONE A; 13,14 BIS O BENZYL GUTTIFERONE A; 13,14 BIS O BUTYRATE GUTTIFERONE A; 13,14 BIS O METHOXYMETHYL GUTTIFERONE A; 13,14 BIS O PIVALOATE GUTTIFERONE A; 14 O 2 ETHYL 1,3 DIOXOLANE GUTTIFERONE A; 14 O 2 METHOXY 5 NITROBENZYL GUTTIFERONE A; 14 O ALLYL GUTTIFERONE A; 14 O BENZYL GUTTIFERONE A; 14 O ETHYL GUTTIFERONE A; 14 O ISOPROPYL GUTTIFERONE A; 14 O METHOXYMETHYL GUTTIFERONE A; 14 O METHYL GUTTIFERONE A; 14 O PROPARGYL GUTTIFERONE A; 14 O PROPYL GUTTIFERONE A; CATECHOL; ESTER DERIVATIVE; ETHER DERIVATIVE; GUTTIFERONE A DERIVATIVE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTILEISHMANIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTIPLASMODIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; GROWTH INHIBITION; IN VITRO STUDY; LEISHMANIA DONOVANI; NONHUMAN; PLASMODIUM FALCIPARUM; PROMASTIGOTE; SYMPHONIA GLOBULIFERA; TREE; TRYPANOCIDAL ACTIVITY; TRYPANOSOMA BRUCEI; VERO CELL;

EID: 84878320768     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.04.066     Document Type: Article

References (23)

1. D.J. Newman, G.M. Cragg, J. Nat. Prod. 75 (2012) 311.
2. K.R. Gustafson, J.W. Blunt, M.H.G. Munro, R.W. Fuller, T.C. Mckee, J.H. Cardellina, J.B. Mcmahon, G.M. Cragg, M.R. Boyd, Tetrahedron 48 (1992) 10093.
3. K. Herath, H. Jayasuriya, J.G. Ondeyka, Z.Q. Guan, R.P. Borris, E. Stijfhoorn, D. Stevenson, J.H. Wang, N. Sharma, K. MacNaul, J.G. Menke, A. Ali, M.J. Schulman, S.B. Singh, J. Nat. Prod. 68 (2005) 617.
4. (a) H. Yang, M. Figueroa, S. To, T. Baggett, B. Jiang, M.J. Basile, I.B. Weinstein, E.J. Kennelly, J. Agric. Food Chem. 58 (2010) 4749;
5. (b) R.B. Williams, J. Hoch, T.E. Glass, R. Evans, J.S. Miller, J.H. Wisse, D.G. Kingston, Planta Med. 69 (2003) 864.
6. For review on PPAPs see R. Ciochina, R.B. Grossman, Chem. Rev. 106 (2006) 3963.
7. (a) H. Tosa, M. Iinuma, T. Tanaka, H. Nozaki, S. Ikeda, K. Tsutsui, M. Yamada, S. Fujimori, Chem. Pharm. Bull. 45 (1997) 418;
8. (b) D. Roux, H.A. Hadi, S. Thoret, D. Guenard, O. Thoison, M. Païs, T. Sévenet, J. Nat. Prod. 63 (2000) 1070;
9. (c) W. Hamed, S. Brajeul, F. Mahuteau-Betzer, O. Thoison, S. Mons, B. Delpech, N. Van Hung, T. Sévenet, C. Marazano, J. Nat. Prod. 69 (2006) 774;
10. (d) C. Gey, S. Kyrylenko, L. Hennig, L.H.D. Nguyen, A. Büttner, H.D. Pham, A. Giannis, Angew. Chem. Int. Ed. 46 (2007) 5219;
11. (e) P. Protiva, M.E. Hopkins, S. Baggett, H. Yang, M. Lipkin, P.R. Holt, E.J. Kennelly, W.I. Bernard, Int. J. Cancer 123 (2008) 687;
12. (f) F.T. Martins, D.M. Assis, M.H. dos Santos, I. Camps, M.P. Veloso, M.A. Juliano, L.C. Alves, A.C. Doriguetto, Eur. J. Med. Chem. 44 (2009) 1230;
13. (g) X.M. Gao, T. Yu, F.F.L. Shuk, Y. Zhou, X. Liu, C.F. Qiao, J.Z. Song, S.L. Chen, K. Qian Luo, H.X. Xu, Bioorg. Med. Chem. 18 (2010) 4957.
14. F. Abe, S. Nagafuji, H. Okabe, H. Akahane, E. Estrada-Muniz, M. Huerta-Reyes, R. Reyes-Chilpa, Biol. Pharm. Bull. 27 (2004) 141.
15. S. Ngouela, B.N. Lenta, D.T. Noungoue, J. Ngoupayo, F.F. Boyom, E. Tsamo, J. Gut, P.J. Rosenthal, J.D. Connolly, Phytochemistry 67 (2006) 302.
16. B.N. Lenta, C. Vonthron-Sénécheau, B. Weniger, K.P. Devkota, J. Ngoupayo, M. Kaiser, Q. Naz, M.I. Choudhary, E. Tsamo, N. Sewald, Molecules 12 (2007) 1548.
17. L. Monzote, O. Cuesta-Rubio, A. Matheeussen, T. Van Assche, L. Maes, P. Cos, Phytother. Res. 25 (2011) 458.
18. Y.N. Figueredo, L. García-Pupo, O.C. Rubio, R. Delgado Hernández, Z. Naal, C. Curti, G.L. PardoAndreu, J. Pharmacol. Sci. 116 (2011) 36.
19. G.L. Pardo-Andreu, Y. Nuñez-Figueredo, V.G. Tudella, O. Cuesta-Rubio, F.P. Rodrigues, C.R. Pestana, S.A. Uyemura, A.M. Leopoldino, L.C. Alberici, C. Curti, Toxicol. Appl. Pharmacol. 253 (2011) 282.
20. Y. Fromentin, P. Grellier, J.D. Wansi, M.C. Lallemand, D. Buisson, Org. Lett. 14 (2012) 5054.
21. K.S.T. Dias, J.P. Januario, J. Lopes D'Dego, A.L.T. Dias, M.H. dos Santos, I. Camps, L.F.L. Coelho, J.C. Viegas, Bioorg. Med. Chem. 20 (2012) 2713.
22. S. Lethu, D. Bosc, E. Mouray, P. Grellier, J. Dubois, J. Enzyme Inhib. Med. Chem. 28 (2013) 163.
23. P. Grellier, J. Sarlauskas, Z. Anusevicius, A. Maroziene, C. Houee-Levin, J. Schrevel, N. Cenas, Arch. Biochem. Biophys. 393 (2001) 199.