Further insights of selenium-containing analogues of WC-9 against Trypanosoma cruzi
As a continuation of our project aimed at searching for new chemotherapeutic agents against American trypanosomiasis (Chagas disease), new selenocyanate derivatives were designed, synthesized and biologically evaluated against the clinically more relevant dividing form of Trypanosoma cruzi, the etio...
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Elsevier Ltd
2019
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| 005 | 20230518205741.0 | ||
| 008 | 190410s2019 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-85061838466 | |
| 024 | 7 | |2 cas |a benznidazole, 22994-85-0; cyanic acid, 420-05-3, 661-20-1 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a BMECE | ||
| 100 | 1 | |a Chao, M.N. | |
| 245 | 1 | 0 | |a Further insights of selenium-containing analogues of WC-9 against Trypanosoma cruzi |
| 260 | |b Elsevier Ltd |c 2019 | ||
| 270 | 1 | 0 | |m Szajnman, S.H.; Departamento de Química Orgánica and UMYMFOR (CONICET–FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, Argentina; email: shs@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
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| 504 | |a Rodriguez, J.B., Markey, S.P., Ziffer, H., Preparation of 2(R) and 2(S) methyl-2-methylglycerates (1993) Tetrahedron Asymmetry, 4, pp. 101-108 | ||
| 504 | |a Ramadas, S., Krupadanam, G.L.D., Enantioselective acylation of 2-hydroxymethyl-2,3-dihydrobenzofurans catalysed by lipase from pseudomonas cepacia (amano ps) and total stereoselective synthesis of (-)-(R)-MEM-protected arthrographol (2000) Tetrahedron Asymmetry, 11, pp. 3375-3393 | ||
| 504 | |a Ghanem, A., Aboul-Enein, H.Y., Application of lipases in kinetic resolution of racemates (2005) Chirality, 17, pp. 1-15 | ||
| 504 | |a Ruiz-Castillo, P., Buchwald, S.L., Applications of palladium-catalyzed C-N cross-coupling reactions (2016) Chem Rev, 116, pp. 12564-12649 | ||
| 504 | |a Maiti, D., Buchwald, S.L., Orthogonal Cu- and Pd-based catalyst systems for the O- and N-arylation of aminophenols (2009) J Am Chem Soc, 131, pp. 17423-17429 | ||
| 504 | |a Bruno, N.C., Buchwald, S.L., Synthesis and application of palladium precatalysts that accommodate extremely bulky di-tert-butylphosphino biaryl ligands (2013) Org Lett, 15, pp. 2876-2879 | ||
| 504 | |a Bhayana, B., Fors, B.P., Buchwald, S.L., A versatile catalyst system for suzuki-miyaura cross-coupling reactions of C(Sp2)-tosylates and mesylates (2009) Org Lett, 11, pp. 3954-3957 | ||
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| 504 | |a Recher, M., Barboza, A.P., Li, Z.-H., Design, synthesis and biological evaluation of sulfur-containing 1,1-bisphosphonic acids as antiparasitic agents (2013) Eur J Med Chem, 60, pp. 431-440 | ||
| 520 | 3 | |a As a continuation of our project aimed at searching for new chemotherapeutic agents against American trypanosomiasis (Chagas disease), new selenocyanate derivatives were designed, synthesized and biologically evaluated against the clinically more relevant dividing form of Trypanosoma cruzi, the etiologic agent of this illness. In addition, in order to establish the role of each part of the selenocyanate moiety, different derivatives, in which the selenium atom or the cyano group were absent, were conceived, synthesized and biologically evaluated. In addition, in order to study the optimal position of the terminal phenoxy group, new regioisomers of WC-9 were synthesized and evaluated against T. cruzi. Finally, the resolution of a racemic mixture of a very potent conformationally rigid analogue of WC-9 was accomplished and further tested as growth inhibitors of T. cruzi proliferation. The results provide further insight into the role of the selenocyanate group in its antiparasitic activity. © 2019 Elsevier Ltd |l eng | |
| 536 | |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica, PICT 2015 1349 | ||
| 536 | |a Detalles de la financiación: Foundation for the National Institutes of Health, AI-107663 | ||
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires, 20020170100067BA | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas, PIP 112-201501-00631 CO | ||
| 536 | |a Detalles de la financiación: We thank Melissa Storey for technical help with the drug screening. This work was supported by grants from the Consejo Nacional de Investigaciones Científicas y Técnicas ( PIP 112-201501-00631 CO ), Agencia Nacional de Promoción Científica y Tecnológica ( PICT 2015 1349 ), and the Universidad de Buenos Aires ( 20020170100067BA ) to J.B.R., and the U.S. National Institutes of Health to R.D. ( AI-107663 ). Appendix A | ||
| 593 | |a Departamento de Química Orgánica and UMYMFOR (CONICET–FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, Buenos Aires, C1428EHA, Argentina | ||
| 593 | |a Center for Tropical and Emerging Global Diseases and Department of Cellular Biology, University of Georgia, Athens, GA 30602, United States | ||
| 690 | 1 | 0 | |a 2 PHENOXYPHENOXYETHYL SELENOCYANATE |
| 690 | 1 | 0 | |a 2 PHENOXYPHENOXYETHYL THIOCYANATE |
| 690 | 1 | 0 | |a 3 (4 PHENOXYPHENOXY)PROPYL CYANIDE |
| 690 | 1 | 0 | |a 4 METHOXYPHENOXYETHYL SELENOCYANATE |
| 690 | 1 | 0 | |a 4 NITROPHENOXYETHYL SELENOCYANATE |
| 690 | 1 | 0 | |a 4 PHENOXYPHENOXYETHYL CYANIDE |
| 690 | 1 | 0 | |a 5 PHENOXY 2 (SELENOCYANATOMETHYL) 2,3 DIHYDROBENZOFURAN |
| 690 | 1 | 0 | |a ANTIPARASITIC AGENT |
| 690 | 1 | 0 | |a BENZNIDAZOLE |
| 690 | 1 | 0 | |a CYANIC ACID |
| 690 | 1 | 0 | |a PHENOXYETHYL SELENOCYANATE |
| 690 | 1 | 0 | |a SELENIUM DERIVATIVE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a [2 (3 PHENOXYPHENOXY)ETHYL](TRIFLUOROMETHYL)SELANE |
| 690 | 1 | 0 | |a [2 (3 PHENOXYPHENOXY)ETHYL](TRIFLUOROMETHYL)SULFANE |
| 690 | 1 | 0 | |a [2 (4 PHENOXYPHENOXY)ETHYL](TRIFLUOROMETHYL)SELANE |
| 690 | 1 | 0 | |a [2 (4 PHENOXYPHENOXY)ETHYL](TRIFLUOROMETHYL)SULFANE |
| 690 | 1 | 0 | |a AMASTIGOTE |
| 690 | 1 | 0 | |a ANTIPARASITIC ACTIVITY |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CONTROLLED STUDY |
| 690 | 1 | 0 | |a CYTOTOXICITY TEST |
| 690 | 1 | 0 | |a DRUG DESIGN |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a ED50 |
| 690 | 1 | 0 | |a GROWTH INHIBITION |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 690 | 1 | 0 | |a VERO CELL LINE |
| 700 | 1 | |a Lorenzo-Ocampo, M.V. | |
| 700 | 1 | |a Szajnman, S.H. | |
| 700 | 1 | |a Docampo, R. | |
| 700 | 1 | |a Rodriguez, J.B. | |
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