Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii

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Abstract As a part of our project aimed at searching for new safe chemotherapeutic agents against parasitic diseases, several compounds structurally related to the antiparasitic agent WC-9 (4-phenoxyphenoxyethyl thiocyanate), which were modified at the terminal phenyl ring, were designed, synthesize...

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Autor principal: Chao, M.N
Otros Autores: Matiuzzi, C.E, Storey, M., Li, C., Szajnman, S.H, Docampo, R., Moreno, S.N.J, Rodriguez, J.B
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: John Wiley and Sons Ltd 2015
Acceso en línea:Registro en Scopus
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024 7 |2 scopus  |a 2-s2.0-84930657427 
024 7 |2 cas  |a thiocyanate, 302-04-5; Antiprotozoal Agents; thiocyanate; Thiocyanates 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a CHEMG 
100 1 |a Chao, M.N. 
245 1 0 |a Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii 
260 |b John Wiley and Sons Ltd  |c 2015 
270 1 0 |m Rodriguez, J.B.; Departamento de Química Orgánica, Universidad de Buenos Aires, Ciudad UniversitariaArgentina 
506 |2 openaire  |e Política editorial 
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504 |a Elicio, P.D., Chao, M.N., Galizzi, M., Li, C., Szajnman, S.H., Docampo, R., Moreno, S.N.J., Rodriguez, J.B., (2013) Eur. J. Med. Chem., 69, pp. 480-489 
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520 3 |a Abstract As a part of our project aimed at searching for new safe chemotherapeutic agents against parasitic diseases, several compounds structurally related to the antiparasitic agent WC-9 (4-phenoxyphenoxyethyl thiocyanate), which were modified at the terminal phenyl ring, were designed, synthesized, and evaluated as growth inhibitors against Trypanosoma cruzi, the etiological agent of Chagas disease, and Toxoplasma gondii, the parasite responsible of toxoplasmosis. Most of the synthetic analogues exhibited similar antiparasitic activity and were slightly more potent than our lead WC-9. For example, two trifluoromethylated derivatives exhibited ED50 values of 10.0 and 9.2 μM against intracellular T. cruzi, whereas they showed potent action against tachyzoites of T. gondii (ED50 values of 1.6 and 1.9 μM against T. gondii). In addition, analogues of WC-9 in which the terminal aryl group is in the meta position with respect to the alkyl chain bearing the thiocyanate group showed potent inhibitory action against both T. cruzi and T. gondii at the very low micromolar range, which suggests that a para-phenyl substitution pattern is not necessary for biological activity. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.  |l eng 
536 |a Detalles de la financiación: National Institutes of Health, NIH, AI-102254 
536 |a Detalles de la financiación: National Institutes of Health, NIH, AI-107663 
593 |a Departamento de Química Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, Buenos Aires, C1428EHA, Argentina 
593 |a Center for Tropical and Emerging Global Diseases, Department of Cellular Biology, University of Georgia, Athens, GA 30602, United States 
690 1 0 |a ANTIPARASITIC AGENTS 
690 1 0 |a BIOLOGICAL ACTIVITY 
690 1 0 |a CHEMOTHERAPEUTIC AGENTS 
690 1 0 |a INHIBITORS 
690 1 0 |a STRUCTURE-ACTIVITY RELATIONSHIPS 
690 1 0 |a 3 (2 CHLOROPHENOXY)PHENOXYETHANOL 
690 1 0 |a 3 (2 CHLOROPHENOXY)PHENOXYETHYL 4 TOLUENESULFONATE 
690 1 0 |a 3 (2 CHLOROPHENOXY)PHENOXYETHYL TETRAHYDRO 2H PYRAN 2 YL ETHER 
690 1 0 |a 3 (2 CHLOROPHENOXY)PHENOXYETHYL THIOCYANATE 
690 1 0 |a 3 (3 CHLOROPHENOXY)PHENOXYETHYL TETRAHYDRO 2H PYRAN 2 YL ETHER 
690 1 0 |a 4 (PYRIDIN 2 YLOXY)PHENOXYETHANOL 
690 1 0 |a 4 (PYRIDIN 2 YLOXY)PHENOXYETHYL 4 TOLUENESULFONATE 
690 1 0 |a 4 (PYRIDIN 2 YLOXY)PHENOXYETHYL TETRAHYDRO 2H PYRAN 2 YL ETHER 
690 1 0 |a 4 (PYRIDIN 2 YLOXY)PHENOXYETHYL THIOCYANATE 
690 1 0 |a 4 BENZYLOXYPHENOXYETHYL TETRAHYDRO 2H PYRAN 2 YL ETHER 
690 1 0 |a 4 HYDROXYPHENOXYETHYL TETRAHYDRO 2H PYRAN 2 YL ETHER 
690 1 0 |a 4 [(3 TRIFLUORO)PHENOXY]PHENOXYETHANOL 
690 1 0 |a 4 [(3 TRIFLUORO)PHENOXY]PHENOXYETHYL 4 TOLUENESULFONATE 
690 1 0 |a 4 [(3 TRIFLUORO)PHENOXY]PHENOXYETHYL TETRAHYDRO 2H PYRAN 2 YL ETHER 
690 1 0 |a 4 [(3 TRIFLUORO)PHENOXY]PHENOXYETHYL THIOCYANATE 
690 1 0 |a 4 [(4 TRIFLUORO)PHENOXY]PHENOXYETHANOL 
690 1 0 |a 4 [(4 TRIFLUORO)PHENOXY]PHENOXYETHYL 4 TOLUENESULFONATE 
690 1 0 |a 4 [(4 TRIFLUORO)PHENOXY]PHENOXYETHYL TETRAHYDRO 2H PYRAN 2 YL ETHER 
690 1 0 |a 4 [(4 TRIFLUORO)PHENOXY]PHENOXYETHYL THIOCYANATE 
690 1 0 |a ALPHA NAPHTHYLOXYPHENYLETHANOL 
690 1 0 |a ALPHA NAPHTHYLOXYPHENYLETHYL 4 TOLUENESULFONATE 
690 1 0 |a ALPHA NAPHTHYLOXYPHENYLETHYL TETRAHYDRO 2H PYRAN 2 YL ETHER 
690 1 0 |a ALPHA NAPHTHYLOXYPHENYLETHYL THIOCYANATE 
690 1 0 |a ANTIPARASITIC AGENT 
690 1 0 |a ARYLOXYETHYL THIOCYANATE DERIVATIVE 
690 1 0 |a BETA NAPHTHYLOXYPHENOXYETHANOL 
690 1 0 |a BETA NAPHTHYLOXYPHENOXYETHYL 4 TOLUENESULFONATE 
690 1 0 |a BETA NAPHTHYLOXYPHENOXYETHYL TETRAHYDRO 2H PYRAN 2 YL ETHER 
690 1 0 |a THIOCYANIC ACID DERIVATIVE 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a UNINDEXED DRUG 
690 1 0 |a ANTIPROTOZOAL AGENT 
690 1 0 |a THIOCYANATE 
690 1 0 |a THIOCYANIC ACID DERIVATIVE 
690 1 0 |a ANTIPARASITIC ACTIVITY 
690 1 0 |a ANTIPROTOZOAL ACTIVITY 
690 1 0 |a ARTICLE 
690 1 0 |a CHAGAS DISEASE 
690 1 0 |a CRYSTAL STRUCTURE 
690 1 0 |a CYTOTOXICITY 
690 1 0 |a DRUG SCREENING 
690 1 0 |a DRUG STRUCTURE 
690 1 0 |a DRUG SYNTHESIS 
690 1 0 |a IN VITRO STUDY 
690 1 0 |a MICROBIAL GROWTH 
690 1 0 |a NUCLEAR MAGNETIC RESONANCE 
690 1 0 |a PRIORITY JOURNAL 
690 1 0 |a TACHYZOITE 
690 1 0 |a TOXOPLASMA GONDII 
690 1 0 |a TOXOPLASMOSIS 
690 1 0 |a TRYPANOSOMA CRUZI 
690 1 0 |a VERO CELL LINE 
690 1 0 |a ANIMAL 
690 1 0 |a CHLOROCEBUS AETHIOPS 
690 1 0 |a DRUG EFFECTS 
690 1 0 |a GROWTH, DEVELOPMENT AND AGING 
690 1 0 |a TOXOPLASMA 
690 1 0 |a TRYPANOSOMA CRUZI 
690 1 0 |a ANIMALS 
690 1 0 |a ANTIPROTOZOAL AGENTS 
690 1 0 |a CERCOPITHECUS AETHIOPS 
690 1 0 |a THIOCYANATES 
690 1 0 |a TOXOPLASMA 
690 1 0 |a TRYPANOSOMA CRUZI 
690 1 0 |a VERO CELLS 
700 1 |a Matiuzzi, C.E. 
700 1 |a Storey, M. 
700 1 |a Li, C. 
700 1 |a Szajnman, S.H. 
700 1 |a Docampo, R. 
700 1 |a Moreno, S.N.J. 
700 1 |a Rodriguez, J.B. 
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