Structure-activity relationship of new growth inhibitors of Trypanosoma cruzi
Several drugs bearing the 4-phenoxyphenoxy skeleton and other closely related structures were designed, synthesized, and evaluated as antiproliferative agents against Trypanosoma cruzi, the etiologic agent of Chagas' disease. The new class of drugs was envisioned by modifying the nonpolar 4-phe...
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1998
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| LEADER | 13313caa a22011897a 4500 | ||
|---|---|---|---|
| 001 | PAPER-2957 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203225.0 | ||
| 008 | 190411s1998 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0032560138 | |
| 024 | 7 | |2 cas |a 4-phenoxyphenoxyethyl thiocyanate; Nifurtimox, 23256-30-6; Phenyl Ethers; Thiocyanates; Trypanocidal Agents | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a JMCMA | ||
| 100 | 1 | |a Cinque, G.M. | |
| 245 | 1 | 0 | |a Structure-activity relationship of new growth inhibitors of Trypanosoma cruzi |
| 260 | |c 1998 | ||
| 270 | 1 | 0 | |m Rodriguez, J.B.; Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina; email: JBR@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
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| 504 | |a Vladusic, E.A., Bussmann, L.E., Visconti, P.E., Stoka, A.M., Rodriguez, J.B., Gros, E.G., Charreau, E.H., Effect of Juvenile Hormone on Mammalian Steroidogenesis (1994) J. Steroid. Biochem. Mol Biol., 50, pp. 181-187 | ||
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| 504 | |a Unpublished results; Docampo, R., Schmuñis, G.A., Sterol Biosynthesis Inhibitors: Potential Chemotherapeutics Against Chagas Disease (1997) Parasitol. Today, 13, pp. 129-130 | ||
| 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., Zhong, L., Docampo, R., Gros, E.G., Biological Evaluation of Two Potent Inhibitors of Trypanosoma cruzi epimastigotes against the Intracellular Form of the Parasite (1996) BioMed. Chem. Lett., 6, pp. 2783-2786 | ||
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| 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 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 | ||
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| 520 | 3 | |a Several drugs bearing the 4-phenoxyphenoxy skeleton and other closely related structures were designed, synthesized, and evaluated as antiproliferative agents against Trypanosoma cruzi, the etiologic agent of Chagas' disease. The new class of drugs was envisioned by modifying the nonpolar 4-phenoxyphenoxy moiety replacing selected aromatic protons by different groups via electrophilic aromatic substitution reactions as well as introducing a sulfur atom at file polar extreme. Of the designed compounds, sulfur-containing derivatives were shown to be potent antireplicative agents against T. cruzi. Among these drugs, 4-phenoxyphenoxyethyl thiocyanate (compound 56) proved to be an extremely active growth inhibitor of the epimastigote forms of T. cruzi and displayed an IC500 of 2.2 μM. Under the same assay conditions, this drug was much more active than Nifurtimox, one of the drugs currently in clinical use to control this disease. This thiocyanate derivative was also a very active inhibitor against the intracellular form of the parasite at the nanomolar level. Other sulfur derivatives prepared also exhibited very potent antiproliferative action against T. cruzi. The presence of a sulfur atom at the polar extreme for this family of compounds seems to be very important for biological action because this atom was always associated with high inhibition values. 4-Phenoxyphenoxyethyl thiocyanate presents very good prospective not only as a lead drug but also as a potential chemotherapeutic agent. |l eng | |
| 593 | |a Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Ciudad Universitaria, 1428 Buenos Aires, Argentina | ||
| 593 | |a Laboratory of Molecular Parasitology, College of Veterinary Medicine, Univ. Illinois at Urbana-Champaign, 2001 South Lincoln Avenue, Urbana, IL 61801, United States | ||
| 690 | 1 | 0 | |a 4 PHENOXYPHENOXYETHYL THIOCYANATE |
| 690 | 1 | 0 | |a NIFURTIMOX |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CHAGAS DISEASE |
| 690 | 1 | 0 | |a DRUG SCREENING |
| 690 | 1 | 0 | |a DRUG STRUCTURE |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a EPIMASTIGOTE |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 690 | 1 | 0 | |a ANIMALS |
| 690 | 1 | 0 | |a DRUG EVALUATION, PRECLINICAL |
| 690 | 1 | 0 | |a NIFURTIMOX |
| 690 | 1 | 0 | |a PHENYL ETHERS |
| 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 Szajnman, S.H. | |
| 700 | 1 | |a Zhong, L. | |
| 700 | 1 | |a Docampo, R. | |
| 700 | 1 | |a Schvartzapel, A.J. | |
| 700 | 1 | |a Rodriguez, J.B. | |
| 700 | 1 | |a Gros, E.G. | |
| 773 | 0 | |d 1998 |g v. 41 |h pp. 1540-1554 |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/jm970860z |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00222623_v41_n9_p1540_Cinque |y Handle |
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