Design, synthesis, and biological evaluation of new growth inhibitors of Trypanosoma cruzi (epimastigotes)
As a continuation of our project aimed at the search for new chemotherapeutic agents against Chagas' disease, several drugs structurally related to the insect growth regulator Fenoxycarb and the naturally occurring juvenfie hormone of insects were designed, synthesized, and evaluated as antipro...
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1997
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 11504caa a22011057a 4500 | ||
|---|---|---|---|
| 001 | PAPER-3223 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203241.0 | ||
| 008 | 190411s1997 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0030749916 | |
| 024 | 7 | |2 cas |a Trypanocidal Agents | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a JMCMA | ||
| 100 | 1 | |a Schvartzapel, A.J. | |
| 245 | 1 | 0 | |a Design, synthesis, and biological evaluation of new growth inhibitors of Trypanosoma cruzi (epimastigotes) |
| 260 | |c 1997 | ||
| 270 | 1 | 0 | |m Rodriguez, J.B.; Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon 2, 1428 Buenos Aires, Argentina; email: jbr@quimor.qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Kirchhoff, L.V., American Trypanosomiasis (Chagas' Disease)-A Tropical Disease now in the United States (1993) N. Engl. J. Med., 329, pp. 639-644 | ||
| 504 | |a Galel, S.A., Kirchhoff, L.V., Risk factors for Trypanosoma cruzi infection in California blood donors (1996) Transfusion, 36, pp. 227-231 | ||
| 504 | |a Marr, J.J., Docampo, R., Chemotherapy for Chagas' Disease: A Perspective of Current Therapy and Considerations for Future Research (1986) Rev. Infect. Dis., 8, pp. 884-903 | ||
| 504 | |a Docampo, R., Moreno, S.N.J., Biochemical Toxicology of Antiparasitic Compounds Used in the Chemotherapy and Chemoprophilaxis of American Trypanosomiaisis (Chagas' Disease) (1985) Rev. Biochem. Toxicoi., 7, pp. 159-204 | ||
| 504 | |a Gutteridge, W.E., Existing Chemotherapy and its Limitations (1985) Br. Med. Bull., 41, pp. 162-168 | ||
| 504 | |a Rodriguez, J.B., Gros, E.G., Recent Developments in the Control of Trypanosoma cruzi, the Causative Agent for Chagas' Disease (1995) Curr. Med. Chem., 2, pp. 723-742 | ||
| 504 | |a Nussenzweig, V., Sonntag, R., Biancalana, A., Pedreira De Fleitas, J.L., Amato Neto, V., Kloetzel, J., Acão de Corantes Trifenil-metanicos sobre o Trypanosoma cruzi "in vitro." Emprêgo de Violeta de Genciana na Profilaxia da Transmissão da Moléstia de Chagas por Transfusão de Sangue (1953) Hospital (Rio de Janeiro), 44, pp. 731-744 | ||
| 504 | |a De Souza, W., Cell Biology of Trypanosoma cruzi (1984) Int. Rev. Cytol., 86, pp. 197-283 | ||
| 504 | |a Kramer, S.J., Law, J.H., Synthesis and Transport of Juvenile Hormones in Insects (1980) Acc. Chem. Res., 13, pp. 297-303 | ||
| 504 | |a Rodriguez, J.B., Gros, E.G., Stoka, A.M., Synthesis and Activity of Juvenile Hormone Analogues (JHA) (1988) Z. Naturforsch., 43 B, pp. 1038-1042 | ||
| 504 | |a Rodriguez, J.B., Gros, E.G., Stoka, A.M., Synthesis and Activity of Juvenile Hormone Analogues (JHA). Part II (1989) Z. Naturforsch., 44 B, pp. 983-987 | ||
| 504 | |a Perlawagora-Szumlewicz, A., Petana, W.P., Figueiredo, M.J., The Evaluation of Host Efficiency and Vector Potential of Laboratory Juvenilized Vector of Chagas' Disease. I - Effects of Developmental Changes Induced by Juvenile Hormone Analogues in Pantrongylus megistus (Hemiptera -Reduviidae) on the Susceptibility of Insects to gut Infection with Trypanosoma cruzi (1975) Rev. Inst. Med. Trap., 17, p. 97 | ||
| 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 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., 45 B, pp. 96-98 | ||
| 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 Masner, P., Dorn, S., Vogel, W., Kaelin, M., Graf, O., Guenthart, E., Types of Response of Insects to a New Insect Growth Regulators and to a Proven Standards (1981) Pr. Nauk. Inst. Chem. Org. Fiz. Politech. Wroclaw, 22, pp. 809-818 | ||
| 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 | ||
| 504 | |a Vladusic, E.A., Pignataro, O.P., Bussmann, L.E., Charreau, E.H., Regulation of the Cholesterol Ester Cycle and Progesterone Synthesis by Juvenile Hormone in MA-10 Leydig Tumor Cells (1995) J. Steroid. Biochem. Mol. Biol., 52, pp. 83-90 | ||
| 504 | |a Urbina, J.A., Payares, G., Molina, J., Sanoja, C., Liendo, A., Lazardi, K., Piras, M.M., Ryley, J.F., Cure of Short- and Long-Term Experimental Chagas' Disease Using D0870 (1996) Science, 273, pp. 969-971 | ||
| 504 | |a Sanchez Delgado, R.A., Lazardi, K., Rincón, L., Urbina, J.A., Hubert, A.J., Noels, A.N., Toward a Novel Metal-Based Chemotherapy against Tropical Diseases. 1. Enhancement of the Efficacy of Clotrimazole against Trypanosoma cruzi by Complexation to Ruthenium in RuCl2(clotrimazole)2 (1993) J. Med. Chem., 36, pp. 2041-2043 | ||
| 504 | |a Farrell, N.P., Williamson, J., McLaren, D.J.M., Trypanocidal and Antitumor Activity of Platinum-Metal and Platinum-Metal-Drug Dual-Function Complexes (1984) Biochem. Pharmacol., 33, pp. 961-971 | ||
| 504 | |a Mesa Valle, C.M., Moraleda-Lindez, V., Craciunescu, D.G., Alonso, M.P., Osuna, A., In vitro Action of New Organometallic Compounds against Trypanosomatidae Protozoa (1993) Arzneim.-Forsch./Drug Res., 43 (2), pp. 1010-1013 | ||
| 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 | ||
| 504 | |a Fichera, L., Esteva, M., Wimmer, Z., Rodriguez, J.B., Gros, E.G., Effects of Juvenile Hormone Analogues (JHA) on the Development of Trypanosoma cruzi (1995) Z. Naturforsch., 50 C, pp. 578-580 | ||
| 504 | |a Scrimin, P., Tecilla, P., Tonellato, U., Cationic Metallovesicles: Catalysis of the Cleavage of p-Nitrophenyl Picolinate and Control of Copper(II) Permeation (1992) J. Am. Chem. Soc., 114, pp. 5086-5092 | ||
| 504 | |a Miyashita, N., Yoshikoshi, A., Grieco, P.A., Pyridinium p-Toluensulfonate. A Mild and Efficient Catalyst for the Tetrahydropyranylation of Alcohols (1977) J. Org. Chem., 42, pp. 3772-3774 | ||
| 504 | |a Agarwal, K.L., Khorana, H.G., Studies on Polynucleotides. CII. The Use of Aromatic Isocyanates for Selective Blocking of the Terminal 3′-Hydroxyl Group in Protected Deoxyribooligonucleotides (1972) J. Am. Chem. Soc., 94, pp. 3578-3585 | ||
| 504 | |a Fieser, L.F., Herz, J.E., Klohs, M.W., Romero, M.A., Utne, T., Cathylation (Carbethoxylation) of Steroid Alcohols (1952) J. Am. Chem. Soc., 74, pp. 3309-3313 | ||
| 504 | |a Johnstone, R.A.W., Rose, M.E., A Rapid, Simple, and Mild Procedure for Alkylation of Phenols, Alcohols, Amides and Acids (1979) Tetrahedron, 75, p. 2169 | ||
| 504 | |a Brown, H.C., (1975) Organic Syntheses Via Boranes, pp. 18-21. , John Wiley: New York | ||
| 504 | |a Zweifel, G., Brown, H.C., Hydration of Olefins, Dienes, and Acetylenes via Hydroboration (1963) Org. React., 13, pp. 1-53 | ||
| 504 | |a Brown, H.C., Hydroboration - A Powerful Synthetic Tool (1961) Tetrahedron, 12, pp. 117-138 | ||
| 504 | |a March, J., (1992) Advanced Organic Chemistry, 4th Ed., pp. 443-444. , John Wiley: New York | ||
| 504 | |a Block, E., Ahmat, S., Catafalmo, J.L., Jain, M.K., Apitz-Castro, R., Antithrombotic Organosulfur Compounds from Garlic: Structural, Mechanistic and Synthetic Studies (1986) J. Am. Chem. Soc., 108, pp. 7045-7055 | ||
| 504 | |a Apitz-Castro, R., Jain, M.K., Bartoli, F., Ledezma, E., Ruiz, M.C., Salas, R., Evidence for Direct Coupling of Primary Agonist-Receptor Interacion to the Exposure of Functional IIb-IIIa Complexes in Human Blood Platelets. Results from Studies with the Antiplatelet Ajoene (1991) Biochem. Biophys. Acta, 1095, pp. 269-280 | ||
| 504 | |a Urbina, J.A., Marchan, E., Lazardi, K., Visbal, G., Apitz-Castro, R., Gil, F., Aguirre, T., Piras, R., Inhibition of Phosphatidylcholine Biosynthesis and Cell Proliferation in Trypanosoma cruzi by Ajoene, an Antiplatelet Compound Isolated from Garlic (1993) Biochem. Pharmacol., 45, pp. 2381-2387 | ||
| 504 | |a Still, W.C., Kahn, M., Mitra, A., Rapid Chromatographic Technique for Preparative Separations with Moderate Resolution (1978) J. Org. Chem., 43, pp. 2923-2925 | ||
| 520 | 3 | |a As a continuation of our project aimed at the search for new chemotherapeutic agents against Chagas' disease, several drugs structurally related to the insect growth regulator Fenoxycarb and the naturally occurring juvenfie hormone of insects were designed, synthesized, and evaluated as antiproliferative agents against the parasite responsible of this disease. Isoprenoid derivatives (compounds 33, 34, 36, and 37) were potent growth inhibitors of Trypanosoma cruzi epimastigotes. In addition, taking into account the high activity observed for compound 30 and the inhibitory action of related compounds, the allyl ether moiety bonded at the polar extreme of these inhibitors proved to be a promising group for the design of new drugs. |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, Department of Pathobiology, Univ. Illinois at Urbana-Champaign, 2001 South Lincoln Avenue, Urbana, IL 61801, United States | ||
| 690 | 1 | 0 | |a 3,7 DIMETHYLOCTA 2,6 DIEN 1 YL ETHYLCARBAMATE |
| 690 | 1 | 0 | |a 3,7 DIMETHYLOCTA 2,6 DIEN 1 YL TETRAHYDRO 2H PYRAN 2 YL ETHER |
| 690 | 1 | 0 | |a 3,7,11 TRIMETHYLDODECA 2,6,10 TRIEN 1 YL ETHYLCARBAMATE |
| 690 | 1 | 0 | |a 3,7,11 TRIMETHYLDODECA 2,6,10 TRIEN 1 YL TETRAHYDRO 2H PYRAN 2 YL ETHER |
| 690 | 1 | 0 | |a 4 BENZOYLPHENYL PROP 2 EN 1 YL ETHER |
| 690 | 1 | 0 | |a BENZNIDAZOLE |
| 690 | 1 | 0 | |a FENOXYCARB |
| 690 | 1 | 0 | |a ISOPRENOID |
| 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 DESIGN |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a EPIMASTIGOTE |
| 690 | 1 | 0 | |a STRUCTURE ACTIVITY RELATION |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 690 | 1 | 0 | |a ANIMALS |
| 690 | 1 | 0 | |a DRUG DESIGN |
| 690 | 1 | 0 | |a MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a MASS SPECTROMETRY |
| 690 | 1 | 0 | |a MOLECULAR STRUCTURE |
| 690 | 1 | 0 | |a SPECTROPHOTOMETRY, INFRARED |
| 690 | 1 | 0 | |a TRYPANOCIDAL AGENTS |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 700 | 1 | |a Zhong, L. | |
| 700 | 1 | |a Docampo, R. | |
| 700 | 1 | |a Rodriguez, J.B. | |
| 700 | 1 | |a Gros, E.G. | |
| 773 | 0 | |d 1997 |g v. 40 |h pp. 2314-2322 |k n. 15 |p J. MED. CHEM. |x 00222623 |w (AR-BaUEN)CENRE-686 |t Journal of Medicinal Chemistry | |
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