Design and synthesis of aryloxyethyl thiocyanate derivatives as potent inhibitors of Trypanosoma cruzi proliferation
As a part of our project directed at the search of new chemotherapeutic agents against American trypanosomiasis (Chagas' disease), several drugs possessing the 4-phenoxyphenoxy skeleton and other closely related structures employing the thiocyanate moiety as polar end group were designed, synth...
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2000
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| LEADER | 15837caa a22013577a 4500 | ||
|---|---|---|---|
| 001 | PAPER-2350 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203144.0 | ||
| 008 | 190411s2000 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0034030531 | |
| 024 | 7 | |2 cas |a Indicators and Reagents; Thiocyanates; Trypanocidal Agents | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a JMCMA | ||
| 100 | 1 | |a Szajnman, S.H. | |
| 245 | 1 | 0 | |a Design and synthesis of aryloxyethyl thiocyanate derivatives as potent inhibitors of Trypanosoma cruzi proliferation |
| 260 | |c 2000 | ||
| 270 | 1 | 0 | |m Rodriguez, J.B.; Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, RA-1428 Buenos Aires, Argentina; email: JBR@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
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| 504 | |a Liendo, A., Lazardi, K., Urbina, J.A., In-vitro antiproliferative effects and mechanism of action of the bis-triazole D0870 and its S(-) enantiomer against Trypanosoma cruzi (1998) J. Antimicrob. Chemother., 41, pp. 197-205 | ||
| 504 | |a Urbina, J.A., Payares, G., Contreras, L.M., Liendo, A., Sanoja, C., Molina, J., Piras, M., Loebenberg, D., Antiproliferative effects and mechanism of action of SCH 56592 against Trypanosoma (Schizotrypanum) cruzi: In vitro and in vivo studies (1998) Antimicrob. Agents Chemother., 42, pp. 1771-1777 | ||
| 504 | |a Docampo, R., Moreno, S.N.J., Turrens, J.F., Katzin, A.M., Gonzalez-Cappa, S.M., Stoppani, A.O.M., Biochemical and ultrastructural alterations produced by miconazole and econazole in Trypanosoma cruzi (1981) Mol. Biochem. Parasitol., 3, pp. 169-180 | ||
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| 504 | |a Rodriguez, J.B., Gros, E.G., Stoka, A.M., Synthesis and activity of juvenile hormone analogues (JHA) for Trypanosoma cruzi (1991) Biomed. Chem. Lett., 1, pp. 679-682 | ||
| 504 | |a Cinque, G.M., Szajnman, S.H., Zhong, L., Docampo, R., Rodriguez, J.B., Gros, E.G., Structure-activity relationship of new growth inhibitors of Trypanosoma cruzi (1998) J. Med. Chem., 41, pp. 1540-1554 | ||
| 504 | |a Schvartzapel, A.J., Zhong, L., Docampo, R., Rodriguez, J.B., Gros, E.G., Design, synthesis and biological evaluation of new growth inhibitors of Trypanosoma cruzi (Epimastigotes) (1997) J. Med. Chem., 40, pp. 2314-2322 | ||
| 504 | |a Schvartzapel, A.J., Fichera, L., Esteva, M., Rodriguez, J.B., Gros, E.G., Design, synthesis, and anti-Trypanosoma cruzi evaluation of a new class of cell growth inhibitors structurally related to Fenoxycarb (1995) Helv. Chim. Acta, 78, pp. 1207-1214 | ||
| 504 | |a Stoka, A.M., Rivas, C., Segura, E., Rodriguez, J.B., Gros, E.G., Biological activity of synthetic juvenile hormone analogues for Trypanosoma cruzi (1990) Z. Naturforsch. B, 45, pp. 96-98 | ||
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| 504 | |a Urbina, J.A., Unpublished information; Rodriguez, J.B., Docampo, R., Gros, E.G., Sulfur-containing derivatives structurally related to fenoxycarb are potent growth inhibitors against the intracellular form of Trypanosoma cruzi (2000) Int. J. Antimicrob. Agents, 13, pp. 215-218 | ||
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| 504 | |a Dimroth, K., Berndt, A., Perst, H., Reichardt, C., 2,4,6-Triphenylphenoxyl (1973) Organic Synthesis, 5, pp. 1130-1134. , Wiley & Sons: New York, Collect | ||
| 504 | |a Newman, N.S., Boden, H., 2,4,5,7-Tetranitrofluorenone (9-fluorenone, 2,4,5,7-tetranitro-) (1973) Organic Synthesis, 5, pp. 1029-1130. , Wiley & Sons: New York, Collect | ||
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| 520 | 3 | |a As a part of our project directed at the search of new chemotherapeutic agents against American trypanosomiasis (Chagas' disease), several drugs possessing the 4-phenoxyphenoxy skeleton and other closely related structures employing the thiocyanate moiety as polar end group were designed, synthesized, and evaluated as antiproliferative agents against Trypanosoma cruzi, the parasite responsible for this disease. These thiocyanate analogues were envisioned bearing in mind the potent activity shown by 4- phenoxyphenoxyethyl thiocyanate (compound 8) taken as lead drug. This compound had previously proved to be an extremely active growth inhibitor against T. cruzi with IC50 values ranging from the very low micromolar level in epimastigotes to the low nanomolar level in the intracellular form of the parasite. Of the designed compounds, the ethyl thiocyanate drugs connected to nonpolar skeletons, namely, arylthio, 2,4-dichlorophenoxy, ortho-substituted aryloxy, and 2-methyl-4-phenoxyphenoxy (compounds 15, 34, 47, 52, 72, respectively), were shown to be very potent antireplicative agents against T. cruzi. On the other hand, conformationally restricted analogues as well as branched derivatives at the aliphatic side chain were shown to be moderately active against T. cruzi growth. The biological activity of drugs bearing the thiocyanate group correlated quite well with the activity exhibited by their normal precursors, the tetrahydropyranyl ether derivatives, when bonded to the same nonpolar skeleton. Compounds having the tetrahydropyranyl moiety as polar end were proportionally much less active than sulfur-containing derivatives in all cases. Drugs 47 and 72 also resulted to be very active against the amastigote form of the parasite growing in myoblasts; however, they were slightly less active than the lead drug 8. On the other hand, compounds 34 and 52 were almost devoid of activity against myoblasts. Surprisingly, the dithio derivative 15 was toxic for myoblasts. |l eng | |
| 593 | |a Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, RA-1428 Buenos Aires, Argentina | ||
| 593 | |a Laboratory of Molecular Parasitology, Department of Pathobiology, Univ. Illinois at Urbana-Champaign, 2001 South Lincoln Avenue, Urbana, IL 61802, United States | ||
| 690 | 1 | 0 | |a 2 (4 PHENOXYPHENYLTHIO)ETHYL THIOCYANIC ACID |
| 690 | 1 | 0 | |a 2 BROMO 4 PHENOXYPHENOXYETHYL THIOCYANIC ACID |
| 690 | 1 | 0 | |a 2 IODO 4 PHENOXYPHENOXYETHYL 4 THIOCYANIC ACID |
| 690 | 1 | 0 | |a 2,4 DICHLOROPHENOXYETHYL THIOCYANIC ACID |
| 690 | 1 | 0 | |a 4 (2 METHYLPHENOXY)PHENOXYETHYL THIOCYANIC ACID |
| 690 | 1 | 0 | |a ANTIPROTOZOAL AGENT |
| 690 | 1 | 0 | |a THIOCYANIC ACID DERIVATIVE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ANTIPROTOZOAL ACTIVITY |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CHAGAS DISEASE |
| 690 | 1 | 0 | |a DRUG POTENCY |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a GROWTH INHIBITION |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a TRYPANOSOMA |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 690 | 1 | 0 | |a TRYPANOSOMIASIS |
| 690 | 1 | 0 | |a ANIMALS |
| 690 | 1 | 0 | |a CELL DIVISION |
| 690 | 1 | 0 | |a DRUG DESIGN |
| 690 | 1 | 0 | |a INDICATORS AND REAGENTS |
| 690 | 1 | 0 | |a MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a MASS SPECTROMETRY |
| 690 | 1 | 0 | |a SPECTROPHOTOMETRY, ULTRAVIOLET |
| 690 | 1 | 0 | |a STRUCTURE-ACTIVITY RELATIONSHIP |
| 690 | 1 | 0 | |a THIOCYANATES |
| 690 | 1 | 0 | |a TRYPANOCIDAL AGENTS |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 700 | 1 | |a Yan, W. | |
| 700 | 1 | |a Bailey, B.N. | |
| 700 | 1 | |a Docampo, R. | |
| 700 | 1 | |a Elhalem, E. | |
| 700 | 1 | |a Rodriguez, J.B. | |
| 773 | 0 | |d 2000 |g v. 43 |h pp. 1826-1840 |k n. 9 |p J. Med. Chem. |x 00222623 |w (AR-BaUEN)CENRE-686 |t Journal of Medicinal Chemistry | |
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| 856 | 4 | 0 | |u https://doi.org/10.1021/jm9905007 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00222623_v43_n9_p1826_Szajnman |y Handle |
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