Synthesis of polysubstituted benzofuran derivatives as novel inhibitors of parasitic growth

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 17, 2013, Pages 4885-4892

  Thévenin, Marion ^a   Thoret, Sylviane ^a   Grellier, Philippe ^b   Dubois, Joëlle ^a  

^a CNRS   (France)

^b MUSÉUM NATIONAL D'HISTOIRE NATURELLE   (France)

Author keywords

Antiparasitic; Benzofurans; P. falciparum; Sonogashira coupling reaction; T. brucei

Indexed keywords

(2 CYCLOPROPYLBENZOFURAN 3 YL)(PHENYL)METHANONE; (2 HYDROXY 4,6 DIMETHOXYPHENYL)[2 (4 METHOXYPHENYL)BENZOFURAN 3 YL]METHANONE; (4 NITROPHENYL)(2 PHENYLBENZOFURAN 3 YL)METHANONE; 2 (3,5 DIMETHYLPHENYL)BENZOFURAN 4 OL; 2 (4 METHOXYPHENYL)BENZOFURAN; 2 (4 METHOXYPHENYL)BENZOFURAN 4 OL; 2 (4 METHOXYPHENYL)BENZOFURAN 4 YLBENZOATE; 2 CYCLOPROPYLBENZOFURAN; 2 CYCLOPROPYLBENZOFURAN 4 OL; 2 PHENYLBENZOFURAN; 2 PHENYLBENZOFURAN 4 OL; 4 (BENZYLOXY) 2 (4 METHOXYPHENYL)BENZOFURAN; 4 (BENZYLOXY) 2 CYCLOPROPYLBENZOFURAN; 4 (BENZYLOXY) 2 PHENYLBENZOFURAN; 4 METHOXY 2 (4 METHOXYPHENYL)BENZOFURAN; [2 (4 METHOXYPHENYL)BENZOFURAN 3 YL](4 NITROPHENYL)METHANONE; [2 (4 METHOXYPHENYL)BENZOFURAN 3 YL](PHENYL)METHANONE; [4 HYDROXY 2 (4 METHOXYPHENYL)BENZOFURAN 3 YL](PHENYL)METHANONE; [4 METHOXY 2 (4 METHOXYPHENYL)BENZOFURAN 3 YL](PHENYL)METHANONE; BENZOFURAN DERIVATIVE; CHLOROQUINE; PENTAMIDINE; PHENYL(2 PHENYLBENZOFURAN 3 YL)METHANONE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CONTROLLED STUDY; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ERYTHROCYTE; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; NONHUMAN; PARASITE DEVELOPMENT; PLASMODIUM FALCIPARUM; SONOGASHIRA REACTION; TRYPANOSOMA BRUCEI;

PLASMODIUM FALCIPARUM; TRYPANOSOMA BRUCEI;

ANTIPARASITIC; BENZOFURANS; P. FALCIPARUM; SONOGASHIRA COUPLING REACTION; T. BRUCEI;

ACYLATION; ANTIPROTOZOAL AGENTS; BENZOFURANS; CYCLIZATION; PARASITIC SENSITIVITY TESTS; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOSOMA BRUCEI BRUCEI;

EID: 84881370569     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.07.002     Document Type: Article

References (32)

1. C.J.L. Murray, L.C. Rosenfeld, S.S. Lim, K.G. Andrews, K.J. Foreman, D. Haring, N. Fullman, M. Naghavi, R. Lozano, and A.D. Lopez Lancet 379 2012 413
2. P.P. Simarro, J. Jannin, and P. Cattand PLoS Med 5 2008 174 e55
3. H. El-Diwani, S. Nakkady, O. El-Shabrawy, A.K. Gohar, and O. Hishmat Arch. Pharm. Res. 11 1988 41
4. F.A.E.-F. Ragab, N.M. Eid, G.S. Hassan, and Y.M. Nissan Chem. Pharm. Bull. 60 2012 110
5. J.S. Kaltenbronn, J. Quin Iii, B.R. Reisdorph, S. Klutchko, E.E. Reynolds, K.M. Welch, M.A. Flynn, and A.M. Doherty Eur. J. Med. Chem. 32 1997 425
6. B.F. Abdel-Wahab, H.A. Abdel-Aziz, and E.M. Ahmed Eur. J. Med. Chem. 44 2009 2632
7. M. Masubuchi, H. Ebiike, K.-i. Kawasaki, S. Sogabe, K. Morikami, Y. Shiratori, S. Tsujii, T. Fujii, K. Sakata, M. Hayase, H. Shindoh, Y. Aoki, T. Ohtsuka, and N. Shimma Bioorg. Med. Chem. 11 2003 4463
8. C.-K. Ryu, A.L. Song, J.Y. Lee, J.A. Hong, J.H. Yoon, and A. Kim Bioorg. Med. Chem. Lett. 20 2010 6777
9. E. Ismail, A.A. Tawfik, and N.M. El-Ebrashi Arzneim. -Forsch. 27 1977 1393
10. S.M. Bakunova, S.A. Bakunov, T. Wenzler, T. Barszcz, K.A. Werbovetz, R. Brun, J.E. Hall, and R.R. Tidwell J. Med. Chem. 50 2007 5807
11. S.A. Bakunov, S.M. Bakunova, T. Wenzler, T. Barszcz, K.A. Werbovetz, R. Brun, and R.R. Tidwell J. Med. Chem. 51 2008 6927
12. S.A. Bakunov, S.M. Bakunova, A.S. Bridges, T. Wenzler, T. Barszcz, K.A. Werbovetz, R. Brun, and R.R. Tidwell J. Med. Chem. 52 2009 5763
13. Gibson, P. S.; Lauret, C.; Patent WO 2008/102232 A1, 2008.
14. G. Benaim, V. Hernandez-Rodriguez, S. Mujica-Gonzalez, L. Plaza-Rojas, M.L. Silva, N. Parra-Gimenez, Y. Garcia-Marchan, A. Paniz-Mondolfi, and G. Uzcanga Antimicrob. Agents Chemother. 56 2012 3720
15. Z. Yu, J.A. Brannigan, D.K. Moss, A.M. Brzozowski, A.J. Wilkinson, A.A. Holder, E.W. Tate, and R.J. Leatherbarrow J. Med. Chem. 55 2012 8879
16. S. Wang, P. Li, L. Yu, and L. Wang Org. Lett. 13 2011 5968
17. A. Arcadi, F. Blesi, S. Cacchi, G. Fabrizi, and A. Goggiamani Tetrahedron Lett. 52 2011 5149
18. W. Chen, P. Li, T. Miao, L.-G. Meng, and L. Wang Org. Biomol. Chem. 11 2013 420
19. A. Arcadi, F. Blesi, S. Cacchi, G. Fabrizi, A. Goggiamani, and F. Marinelli Tetrahedron 69 2013 1857
20. F.V. Singh, and T. Wirth Synthesis 44 2012 1171
21. T. Kitamura, and K. Otsubo J. Org. Chem. 77 2012 2978
22. C. Glaser Ber. Dtsch. Chem. Ges. 2 1869 422
23. C. Glaser Ann. Chem. Pharm. 154 1870 137
24. C.C.C. Johansson Seechurn, M.O. Kitching, T.J. Colacot, and V. Snieckus Angew. Chem., Int. Ed. 51 2012 5062
25. M. Jacubert, A. Hamze, O. Provot, J.-F. Peyrat, J.-D. Brion, and M. Alami Tetrahedron Lett. 50 2009 3588
26. J. Guillon, P. Grellier, M. Labaied, P. Sonnet, J.-M. Léger, R. Déprez-Poulain, I. Forfar-Bares, P. Dallemagne, N. Lemaître, F. Péhourcq, J. Rochette, C. Sergheraert, and C. Jarry J. Med. Chem. 47 2004 1997
27. R.E. Desjardins, C.J. Canfield, J.D. Haynes, and J.D. Chulay Antimicrob. Agents Chemother. 16 1979 710
28. D. Bosc, S. Lethu, E. Mouray, P. Grellier, and J. Dubois MedChemComm 3 2012 1512
29. J. O'Brien, I. Wilson, T. Orton, and F. Pognan Eur. J. Biochem. 267 2000 5421
30. H. Hirumi, and K. Hirumi Parasitol. Today 10 1994 80
31. D. Bosc, E. Mouray, P. Grellier, S. Cojean, P.M. Loiseau, and J. Dubois MedChemComm 4 2013 1034
32. B. Räz, M. Iten, Y. Grether-Bühler, R. Kaminsky, and R. Brun Acta Tropica 68 1997 139