Biological evaluation of two potent inhibitors of Trypanosoma cruzi epimastigotes against the intracellular form of the parasite

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(±)-S-Ethyl-[3,7,11]-trimethyl-10,11-epoxy-2E,6E-dien-1-yl]-thiolcarb onate (1) and 4-phenoxyphenoxy ethyl tetrahydropyranyl ether (2) were shown to be very active antireplicative agents against intracellular Trypanosoma cruzi amastigotes in in vitro assays. Both of them had previously presented hig...

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Detalles Bibliográficos
Autor principal: Rodriguez, J.B
Otros Autores: Zhong, L., Docampo, R., Gros, E.G
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 1996
Acceso en línea:Registro en Scopus
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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030 |a BMCLE 
100 1 |a Rodriguez, J.B. 
245 1 0 |a Biological evaluation of two potent inhibitors of Trypanosoma cruzi epimastigotes against the intracellular form of the parasite 
260 |c 1996 
270 1 0 |m Rodriguez, J.B.; Departamento de Quimica Organica, Fac. de Ciencias Exactas/Naturales, Universidad de Buenos Aires, Pabellon 2, 1428 Buenos Aires, Argentina 
506 |2 openaire  |e Política editorial 
504 |a Kirchhoff, L.V., (1993) New Engl. J. Med., 329, p. 639 
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504 |a Marr, J.J., Docampo, R., (1986) Rev. Infect. Dis., 8, p. 884 
504 |a Morello, A., (1988) Comp. Biochem. Physiol., 90 C, p. 1 
504 |a Gutteridge, W.E., (1985) Br. Med. Bull., 41, p. 162 
504 |a Rodriguez, J.B., Gros, E.G., (1995) Curr. Med. Chem., 2, p. 723 
504 |a Nussenzweig, V., Sonntag, R., Biancalana, A., Pedreira De Fleitas, J.L., Amato Neto, V., Kloetzel, J., (1953) Hospital (Rio de Janeiro), 44, p. 731 
504 |a Masner, P., Dorn, S., Vogel, W., Kaelin, M., Graf, O., Guenthart, E., (1981) Pr. Nauk. Inst. Chem. Org. Fiz. Politech. Wroclaw, 22, p. 809 
504 |a Schvartzapel, A.J., Fichera, L., Esteva, M., Rodriguez, J.B., Gros, E.G., (1995) Helv. Chim. Acta, 78, p. 1207 
504 |a Rodriguez, J.B., Gros, E.G., Stoka, A.M., (1991) Bioorg. Med. Chem. Lett., 1, p. 679 
504 |a Stoka, A.M., Rivas, C., Segura, E., Rodriguez, J.B., Gros, E.G., (1990) Z. Naturforsch., 45 B, p. 96 
504 |a Rodriguez, J.B., Gros, E.G., Stoka, A.M., (1988) Z. Naturforsch., 43 B, p. 1038 
504 |a Rodriguez, J.B., Gros, E.G., Stoka, A.M., (1989) Z. Naturforsch., 44 B, p. 983 
504 |a Perlawagora-Szumlewicz, A., Petana, W.P., Figueiredo, M.J., (1975) Rev. Inst. Med. Trop., 17, p. 97 
504 |a Fijisawa, T., Sato, T., Gotoh, Y., Kawashima, M., Kawara, T., (1982) Bull Chem Soc. Jpn., 55, p. 3555. , Selective data for compound 1: HPLC separation gave a relationship of 2.5:1 of epoxides mixture favored to the desired terminal epoxide as a colorless oil. 1 H NMR (200 MHz, CDCl 3 ) δ 5.37 (m, 1 H, H-2); 5.15 (m, 1 H, H-6); 4.73 (d, J = 7.2 Hz, 2 H, H-1); 2.88 (q, J = 7.4 Hz, 2 H, SCH 2 CH 3 ); 2.70 (t, J = 6.2 Hz, 1 H, H-2); 2.10 (m, 6 H, H-4, H-5 and H-8); 1.72 (s, 3 H, Me at C-3); 1.62 (s, 3 H, Me at C-7); 1.32 (t, J = 7.4 Hz, 3 H, SCH 2 CH 3 ); 1.31 (s, 3 H, Me at C-11); 1.27 (s, 3 H, Me at C-7). 13 C RMN δ 15.0 (SCH 2 CH 3 ), 16.0 (Me at C-7), 17.6 (Me at C-3), 18.8 (Me at C-11), 24.8 (C-12), 25.2 (SCH 2 CH 3 ), 26.1 (C-5), 27.4 (C-9), 36.3 (C-8), 39.4 (C-4), 58.0 (C-11), 63.6 (C-10), 63.9 (C-1), 117.6 (C-2), 124.0 (C-6), 134.4 (C-7), 142.9 (C-3), 170.8 (C=O) 
504 |a Johnstone, R., Rose, M., (1979) Tetrahedron, 35, p. 2169 
504 |a Vladusic, E.A., Bussmann, L.E., Visconti, P.E., Stoka, A.M., Rodriguez, J.B., Gros, E.G., Charreau, E.H., (1994) J. Steroid. Biochem. Mol. Biol., 50, p. 181 
504 |a Vladusic, E.A., Pignataro, O.P., Bussmann, L.E., Charreau, E.H., (1995) J. Steroid. Biochem. Mol. Biol., 52, p. 83 
504 |a Urbina, J.A., Payares, G., Molina, J., Sanoja, C., Liendo, A., Lazardi, K., Piras, M.M., Ryley, J.F., (1996) Science, 273, p. 969 
504 |a Fichera, L., Esteva, M., Wimmer, Z., Rodriguez, J.B., Gros, E.G., (1995) Z. Naturforsch., 50 C, p. 578 
504 |a Barr, S.C., Rose, D., Jaynes, J.M., (1995) J. Parasitol., 81, p. 974 
504 |a Moreno, S.N.J., Silva, J., Vercesi, A.E., Docampo, R., (1994) J. Exp. Med., 180, p. 1535 
520 3 |a (±)-S-Ethyl-[3,7,11]-trimethyl-10,11-epoxy-2E,6E-dien-1-yl]-thiolcarb onate (1) and 4-phenoxyphenoxy ethyl tetrahydropyranyl ether (2) were shown to be very active antireplicative agents against intracellular Trypanosoma cruzi amastigotes in in vitro assays. Both of them had previously presented high biological activity as growth inhibitors of the epimastigote form of the parasite.  |l eng 
536 |a Detalles de la financiación: Universidad de Buenos Aires 
536 |a Detalles de la financiación: National Council for Scientific Research 
536 |a Detalles de la financiación: National Institutes of Health, AI23259 
536 |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas 
536 |a Detalles de la financiación: Acknowledgments: The authors would like to thank the National Research Council of Argentina (CONICET) and the University of Buenos Aires for partial financial support and UMYMFOR for spectra and NIH grant AI23259 to R. D. 
593 |a Depto. de Quimica Orgánica, Fac. de Cie. Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, 1428 Buenos Aires, Argentina 
593 |a Dept. of Veterinary Pathobiology, College of Veterinary Medicine, Univ. of Illinois at Urbana-C., 2001 South Lincoln Avenue, Urbana, IL 61801, United States 
690 1 0 |a ANTIPARASITIC AGENT 
690 1 0 |a ANIMAL CELL 
690 1 0 |a ARTICLE 
690 1 0 |a CELL PROLIFERATION 
690 1 0 |a CONTROLLED STUDY 
690 1 0 |a IN VITRO STUDY 
690 1 0 |a MYOBLAST 
690 1 0 |a NONHUMAN 
690 1 0 |a TRYPANOSOMA CRUZI 
690 1 0 |a ANIMALIA 
690 1 0 |a TRYPANOSOMA 
690 1 0 |a TRYPANOSOMA CRUZI 
700 1 |a Zhong, L. 
700 1 |a Docampo, R. 
700 1 |a Gros, E.G. 
773 0 |d 1996  |g v. 6  |h pp. 2783-2786  |k n. 22  |p BIOORG. MED. CHEM. LETT.  |x 0960894X  |w (AR-BaUEN)CENRE-3990  |t Bioorganic and Medicinal Chemistry Letters 
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856 4 0 |u https://doi.org/10.1016/S0960-894X(96)00517-3  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_0960894X_v6_n22_p2783_Rodriguez  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0960894X_v6_n22_p2783_Rodriguez  |y Registro en la Biblioteca Digital 
961 |a paper_0960894X_v6_n22_p2783_Rodriguez  |b paper  |c PE 
962 |a info:eu-repo/semantics/article  |a info:ar-repo/semantics/artículo  |b info:eu-repo/semantics/publishedVersion 
999 |c 79734 

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