Design, synthesis, and biological evaluation of aryloxyethyl thiocyanate derivatives against Trypanosoma cruzi
As a continuation of our project aimed at the search for new and safe chemotherapeutic and chemoprophylactic agents against American trypanosomiasis (Chagas' disease), several drugs structurally related to 4-phenoxyphenoxyethyl thiocyanate (4) were designed, synthesized, and evaluated as antipr...
Guardado en:
| Autor principal: | |
|---|---|
| Otros Autores: | , , , , |
| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
2002
|
| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| LEADER | 15937caa a22012617a 4500 | ||
|---|---|---|---|
| 001 | PAPER-5244 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203452.0 | ||
| 008 | 190411s2002 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0037194642 | |
| 024 | 7 | |2 cas |a ketoconazole, 65277-42-1; Thiocyanates; Trypanocidal Agents | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a JMCMA | ||
| 100 | 1 | |a Elhalem, E. | |
| 245 | 1 | 0 | |a Design, synthesis, and biological evaluation of aryloxyethyl thiocyanate derivatives against Trypanosoma cruzi |
| 260 | |c 2002 | ||
| 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 | ||
| 504 | |a Rodriguez, J.B., Specific molecular targets to control tropical diseases (2001) Curr. Pharm. Des., 7, pp. 1105-1116 | ||
| 504 | |a Augustyns, K., Amssoms, K., Yamani, A., Rajan, P.K., Haemers, A., Trypanothione as a target in the design of antitrypanosomal and antileishmanial agents (2001) Curr. Pharm. Des., 7, pp. 1117-1141 | ||
| 504 | |a Cazzulo, J.J., Stoka, V., Turk, V., The Major cysteine proteinase of Trypanosoma cruzi: A valid target for chemotherapy of chagas disease (2001) Curr. Pharm. Des., 7, pp. 1143-1156 | ||
| 504 | |a Docampo, R., Recent developments in the chemotherapy of Chagas' disease (2001) Curr. Pharm. Des., 7, pp. 1157-1164 | ||
| 504 | |a De Lederkremer, R.M., Bertello, L.E., Glycoinositolphospholipids, free and as anchors of proteins, in Trypanosoma cruzi (2001) Curr. Pharm. Des., 7, pp. 1165-1179 | ||
| 504 | |a (1991) Control of Chagas' Disease, , WHO Technical Report Series, No. 811; World Health Organization: Geneva | ||
| 504 | |a De Castro, S.L., The challenge of Chagas' disease chemotherapy: An update of drugs assayed against Trypanosoma cruzi (1993) Acta Trop., 53, pp. 83-98 | ||
| 504 | |a Docampo, R., Moreno, S.N.J., Biochemical toxicology of antiparasitic compounds used in the chemotherapy and chemoprophylaxis of American trypanosomiaisis (Chagas' Disease) (1985) Rev. Biochem. Toxicol., 7, pp. 159-204 | ||
| 504 | |a Brener, Z., Present status of the chemotherapy and chemoprophylaxis of human trypanosomiasis in the Western Hemisphere (1979) Pharmacol. Ther., 7, pp. 71-90 | ||
| 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 Brener, Z., Biology of Trypanosoma cruzi (1973) Annu. Rev. Microbiol., 27, pp. 347-382 | ||
| 504 | |a Docampo, R., Schmuñis, G., Sterol biosynthesis inhibitors: Potential chemotherapeutics against Chagas Disease (1997) Parasitol. Today, 13, pp. 129-130 | ||
| 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 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 | ||
| 504 | |a Urbina, J.A., Chemotherapy of Chagas' disease: The how and the why (1999) J. Mol. Med., 77, pp. 332-338 | ||
| 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 Szajnman, S.H., Yan, W., Bailey, B.N., Docampo, R., Elhalem, E., Rodriguez, J.B., Design and synthesis of aryloxyethyl thiocyanate derivatives as potent inhibitors of Trypanosoma cruzi proliferation (2000) J. Med. Chem., 43, pp. 1826-1840 | ||
| 504 | |a Urbina, J.A., Unpublished results; Docampo, R., Personal communication; Montalvetti, A., Bailey, B.N., Martin, M.B., Severin, G.W., Oldfield, E., Docampo, R., Bisphosphonates are potent inhibitors of Trypanosoma cruzi farnesyl pyrophosphate synthase (2001) J. Biol. Chem., 276, pp. 33930-33937 | ||
| 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 Tarbell, D.S., Petropoulus, J.C., The action of aluminum bromide on benzyl phenyl ether (1952) J. Am. Chem. Soc., 74, pp. 244-248 | ||
| 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, pp. 2169-2172 | ||
| 504 | |a Miyashita, N., Yoshikoshi, A., Grieco, P.A., Pyridinium pToluensulfonate. A mild and efficient catalyst for the tetrahydropyranylation of alcohols (1977) J. Org. Chem., 42, pp. 3772-3774 | ||
| 504 | |a Witczack, Z.J., Monosaccharide isothiocyanates and thiocyanates: Synthesis, chemistry, and preparative applications (1986) Adv. Carbohydr. Chem. Biochem., 44, pp. 91-145 | ||
| 504 | |a Bellus, D., Photo-Fries rearrangement and related photochemical [1j]-shifts (j: 3, 5, 7) of carbonyl and sulfonyl groups (1971) Advances in Photochemistry, 8, pp. 109-159. , Pitts, J. N., Jr., Hammond, G., Noyes, W. A., Jr., Eds.; Wiley-Interscience: New York | ||
| 504 | |a Meyer, J.W., Hammond, G.S., Mechanism of photochemical reaction in solution LXX. Photolysis of aryl ethers (1972) J. Am. Chem. Soc., 94, pp. 2219-2228 | ||
| 504 | |a Kalmus, C.E., Hercules, D.M., A mechanistic study of the photo-fries rearrangement of phenyl acetate (1974) J. Am. Chem. Soc., 96, pp. 449-456 | ||
| 504 | |a Adam, W., De Sanabia, J.A., Fischer, H., Transient intermediates in the photo-fries isomerization of phenyl acetate via spontaneous raman spectroscopy (1973) J. Org. Chem., 38, pp. 2571-2572 | ||
| 504 | |a Beck, S.M., Brus, L.E., CIDNP evidence for radical pair mechanism in photo-fries rearrangement (1982) J. Am. Chem. Soc., 104, pp. 1805-1808 | ||
| 504 | |a Nakagaki, R., Hiramatsu, M., Watanabe, T., Tanimoto, Y., Hagakura, S., Magnetic isotope and external magnetic field upon the photo-fries rearrangement of 1-naphthyl acetate (1985) J. Phys. Chem., 89, pp. 3222-3226 | ||
| 504 | |a López Quiroga, I., Cimino, R., Nasser, J.R., Rodriguez, J.B., Unpublished results; Chan, D.M.T., Monaco, K.L., Wang, R.-P., Winters, M.P., New N- and O-arylations with phenylboronic acids and cupric acetate (1998) Tetrahedron Lett., 39, pp. 2933-2936 | ||
| 504 | |a Evans, D.A., Katz, J.L., West, T.R., Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine (1998) Tetrahedron Lett., 39, pp. 2937-2940 | ||
| 504 | |a Lam, P.Y.S., Clark, C.G., Saubern, S., Adams, J., Winters, M.P., Chan, M.P.T., Combs, A., New aryl/heteroaryl C-N bond cross-coupling reactions via arylboronic acid/cupric acetate arylation (1998) Tetrahedron Lett., 39, pp. 2941-2944 | ||
| 504 | |a Node, N., Nishide, K., Fuji, K., Fujita, E., Hard acid and soft nucleophile system. 2. Demethylation of methyl ethers of alcohol and phenol with an aluminum halide-thiol system (1980) J. Org. Chem., 45, pp. 4275-4277 | ||
| 504 | |a Jung, M.E., Lyster, M.A., Quantitative dealkylation of alkyl ethers via treatment with trimethylsilyl iodide. A new method for ether hydrolysis (1977) J. Org. Chem., 42, pp. 3761-3764 | ||
| 504 | |a Gallo-Rodriguez, C., Ji, X.-D., Melman, N., Siegman, B.D., Sanders, L.H., Orlina, J., Fischer, B., Jacobson, K.A., Structure-activity relationships of N6-benzyladenosine-5′-uronamides as A3-selective adenosine agonists (1994) J. Med. Chem., 37, pp. 636-646 | ||
| 504 | |a 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 | ||
| 504 | |a Brown, S., Bernardo, M.M., Li, Z.-H., Kotra, L.P., Tanaka, Y., Fridman, R., Mobashery, S., Potent and selective mechanismbased inhibition of gelatinases (2000) J. Am. Chem. Soc., 122, pp. 6799-6800 | ||
| 504 | |a Hajduk, P.J., Bures, M., Praestgaard, J., Fesik, S.W., Privileged molecules for protein binding identified from NMR-based screening (2000) J. Med. Chem., 43, pp. 3443-3447 | ||
| 504 | |a Ittah, Y., Shahak, I., Tsaroom, S., Blum, J., A new aziridine synthesis from 2-azido alcohols and tertiary phosphines. Preparation of phenanthene-9,10-imine (1978) J. Org. Chem., 43, pp. 4271-4273 | ||
| 504 | |a Hiskey, R.G., Harpold, M.A., Chemistry of aliphatic disulfides. XIV. The preparation of disulfides sulfoxides by selective oxidation (1967) J. Org. Chem., 32, pp. 3191-3199 | ||
| 504 | |a Leonard, N.J., Johnson, C.R., Periodate oxidation of sulfides to sulfoxides. Scope of the reaction (1962) J. Org. Chem., 27, pp. 282-284 | ||
| 504 | |a Rodriguez, J.B., Zhong, L., Docampo, R., Wimmer, Z., Gros, E.G., Growth inhibitory effect of juvenile hormone analogues on epimastigotes of Trypanosoma cruzi (1998) Bioorg. Med. Chem. Lett., 8, pp. 3257-3260 | ||
| 504 | |a Ujváry, I., Matolcsy, G., Riddiford, L.M., Hiruma, K., Horwarth, K.L., Inhibition of spiracle and crochet formation and juvenile hormone activity of isothiocyanate derivatives in the tobacco hornworm, Manduca sexta (1989) Pestic. Biochem. Physiol., 35, pp. 259-274 | ||
| 504 | |a Buerstinghaus, R., Hofmeister, P., Kuenast, C., Pesticidal composition and process for combating pests employing carboxamides. U.S. Patent 4,859,706, August 22, 1989; Fischer, U., Schneider, F., Zurflueh, R., Carbamic Acid Derivatives. U.S. Patent 4,215,139, July 29, 1980; Zhang, Y., Talalay, P., Cho, C.-G., Posner, G.H., A major inducer of anticarcinogenic protective enzymes from broccoli: Isolation and elucidation of structure (1992) Proc. Natl. Acad. Sci. U.S.A., 89, pp. 2399-2403 | ||
| 504 | |a Posner, G.H., Cho, C.-G., Green, J.V., Zhang, Y., Talalay, P., Design and synthesis of bifunctional isothiocyanate analogs of sulforaphane: Correlation between structure and potency as inducers of anticarcinogenic detoxification enzymes (1994) J. Med. Chem., 37, pp. 170-176 | ||
| 504 | |a Zhang, Y., Kensler, T.W., Cho, C.-G., Posner, G.H., Talalay, P., Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates (1994) Proc. Natl. Acad. Sci. U.S.A., 91, pp. 3147-3150 | ||
| 504 | |a Yan, W., Moreno, S.N., A method to assess invasion and intracellular replication of Trypanosoma cruzi based on differential uracil incorporation (1998) J. Immunol. Methods, 220, pp. 123-128 | ||
| 504 | |a note | ||
| 520 | 3 | |a As a continuation of our project aimed at the search for new and safe chemotherapeutic and chemoprophylactic agents against American trypanosomiasis (Chagas' disease), several drugs structurally related to 4-phenoxyphenoxyethyl thiocyanate (4) were designed, synthesized, and evaluated as antiproliferative agents against the parasite responsible for this disease, the hemoflagellated protozoan Trypanosoma cruzi. This thiocyanate derivative was previously shown to be an effective and potent agent against T. cruzi proliferation. Several drugs possessing thiocyanate groups proved to be effective growth inhibitors of T. cruzi growth. Among the designed compounds, it is important to point out the extremely potent activity shown by 11, 23, 38, 53, 90, 99, and 117 against the epimastigote forms of the parasite. All of them exhibited IC50 values in the low micromolar range, and these values were comparable with those presented by our lead drug 4 and ketokonazole, a well-known antiparasitic agent. The activity displayed by the nitrogen-containing derivative 90 was very promising with IC50 values of 3.3 μM. Several other thiocyanate derivatives also proved to be very potent inhibitors of the multiplication of T. cruzi epimastigotes, such as compounds 28, 33, 43, 48, 56, 61, 66, 71, 76, and 124. Compound 43 resulted in being a promising drug because it was also very effective against amastigotes, the clinically more relevant form of the parasite. This compound was 3-fold more potent than 4, while 11 showed nearly the same activity as our lead drug against intracellular T. cruzi. It was very surprising that the experimental juvenoid 124, although fairly devoid of activity against epimastigotes, was very effective against intracellular amastigotes growing in myoblasts. The rest of the designed compounds showed a broad degree of inhibitory action, from moderately active drugs to drugs almost devoid of antiparasitic activity. Compound 43 is an interesting example of an effective antichagasic agent that presents excellent prospectives not only as a lead drug but also to be used for further in vivo studies. |l eng | |
| 593 | |a Departamento de Química Organica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, RA-1428 Buenos Aires, Argentina | ||
| 593 | |a Laboratory of Molecular Parasitology, Department of Pathobiology, College of Veterinary Medicine, University of Illinois at Urbana-Champaign, 2001 South Lincoln Avenue, Urbana, IL 61802, United States | ||
| 593 | |a Institute of Chemistry, Chemical Research Center, Hungarian Academy of Sciences, P.O. Box 17, H-1525 Budapest, Hungary | ||
| 690 | 1 | 0 | |a 4 PHENOXYPHENOXYETHYLTHIOCYANATE |
| 690 | 1 | 0 | |a KETOCONAZOLE |
| 690 | 1 | 0 | |a THIOCYANIC ACID DERIVATIVE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a AMASTIGOTE |
| 690 | 1 | 0 | |a ANTIPROTOZOAL ACTIVITY |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CHAGAS DISEASE |
| 690 | 1 | 0 | |a CHEMOPROPHYLAXIS |
| 690 | 1 | 0 | |a DRUG DESIGN |
| 690 | 1 | 0 | |a DRUG POTENCY |
| 690 | 1 | 0 | |a DRUG STRUCTURE |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a EPIMASTIGOTE |
| 690 | 1 | 0 | |a IC 50 |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 690 | 1 | 0 | |a ANIMALS |
| 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 Bailey, B.N. | |
| 700 | 1 | |a Docampo, R. | |
| 700 | 1 | |a Ujváry, I. | |
| 700 | 1 | |a Szajnman, S.H. | |
| 700 | 1 | |a Rodriguez, J.B. | |
| 773 | 0 | |d 2002 |g v. 45 |h pp. 3984-3999 |k n. 18 |p J. Med. Chem. |x 00222623 |w (AR-BaUEN)CENRE-686 |t Journal of Medicinal Chemistry | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-0037194642&doi=10.1021%2fjm0201518&partnerID=40&md5=397df03e90fde9275bf8dd167a76edd6 |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1021/jm0201518 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00222623_v45_n18_p3984_Elhalem |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222623_v45_n18_p3984_Elhalem |y Registro en la Biblioteca Digital |
| 961 | |a paper_00222623_v45_n18_p3984_Elhalem |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 999 | |c 66197 | ||