Submitted by Sandra Pereira (srpereira@ufrrj.br) on 2017-08-29T14:02:13Z
No. of bitstreams: 1
2009 - Breno Almeida Soares.pdf: 7105040 bytes, checksum: 3b6aebf34151816545510b0506ed3412 (MD5) / Made available in DSpace on 2017-08-29T14:02:13Z (GMT). No. of bitstreams: 1
2009 - Breno Almeida Soares.pdf: 7105040 bytes, checksum: 3b6aebf34151816545510b0506ed3412 (MD5)
Previous issue date: 2009-09-25 / Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior, CAPES, Brasil. / This work is part of a research project which investigates the utilization of abundant
and accessible natural products in the synthesis of new molecules with potential activity
against Chagas? disease. Recent studies carried out in our laboratory showed activity
against Trypanosoma cruzi for piperine, a major component of Piper nigrum and for a
series of its derivatives and analogues. Using bioisosterism as a strategy for molecular
modification, we describe here the design, synthesis and antiparasitic evaluation of
class of derivatives of 1,2,4-oxadiazole. The key step of the synthetic strategy used
involved the SNAC reaction of the benzamidoxima with acid chlorides followed by
cyclization, which allowed the preparation of eight new 1,2,4-oxadiazole The evaluation
of the toxic activity of these new derivatives against epimastigote form of T. cruzi
confirmed the bioisosteric relationship between the natural amide and the new products
prepared, showing the oxadiazole 55 direct derived from piperine, as the most active
compound in the series. / Este trabalho se insere numa linha de pesquisa que visa a utiliza??o de produtos
naturais abundantes e access?veis na s?ntese de novas mol?culas com potencial atividade
anti-chag?sica. Estudos recentes em nosso laborat?rio demonstraram a atividade
antiparasit?ria da piperina e de uma s?rie de derivados e an?logos sobre o Trypanosoma
cruzi, agente etiol?gico da doen?a de Chagas. Utilizando o bioisosterismo como
estrat?gia de modifica??o molecular, descrevemos aqui o planejamento, a s?ntese e a
avalia??o antiparasit?ria de derivados da classe dos 1,2,4-oxadiaz?is. A etapa-chave da
estrat?gia sint?tica utilizada envolveu a rea??o de SNAC da benzamidoxima com cloretos
de ?cidos, seguida de cicliza??o, que permitiu a prepara??o de oito novos 1,2,4-
oxadiaz?is. A avalia??o da atividade t?xica destes novos derivados contra a forma
epimastigota do T. cruzi confirmou a rela??o bioisost?rica entre a amida natural e os
novos derivados preparados, evidenciando o oxadiazol 55 derivado direto da piperina,
como o composto mais ativo da s?rie.
| Identifer | oai:union.ndltd.org:IBICT/oai:localhost:jspui/2003 |
| Date | 25 September 2009 |
| Creators | Soares, Breno Almeida |
| Contributors | Lima, Marco Edilson Freire de, Lima, Lidia Moreira, Ferreira, Aur?lio Baird Buarque, Pinheiro, S?rgio |
| Publisher | Universidade Federal Rural do Rio de Janeiro, Programa de P?s-Gradua??o em Qu?mica, UFRRJ, Brasil, Instituto de Ci?ncias Exatas |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/masterThesis |
| Format | application/pdf |
| Source | reponame:Biblioteca Digital de Teses e Dissertações da UFRRJ, instname:Universidade Federal Rural do Rio de Janeiro, instacron:UFRRJ |
| Rights | info:eu-repo/semantics/openAccess |
| Relation | AFIATPOUR, P. ; SRIVASTAVA, R. M. Analgesic and antiinflamatory effects of 3- [3-(phenyl)-1,2,4-oxadiazol-5-yl] propionic acid. Braz. J. Med. Biol. Res. 27 (6), 1403, 1994. ALDRICH. Catalog Handbook of fine chemicals Aldrich. 2005-2006. AINSWORTH, C. Thermanl fragmentation of 1,2,4-oxadiazoles. J. Heterocycl. Chem. 3 (4), 470 ,1966. ATAL, C. K., DHAR, K. L., SINGH, J. Chemistry of Indian Piper species. Loydia- J. Nat. Prod. 38 (3): 256-264, 1975. BANO, G., RAINA, R. K., ZUTSHI, U., BEDI, K. L., JOHRI, R. K., SHARMA, S. C. Effect of piperine on bioavailability and pharmacokinetics of propanolol and theophylline in healthy-volunteers. Eur. J. Clin. Pharm. 41 (6): 615-617, 1991. BAKER, D. D.; CHU, M.; OZA, U.; RAJGARHIA, V. The value of natural products to future pharmaceutical discovery. Nat. Prod. Rep. 24, 1225, 2007. BEHR, L. C., in ?The Chemistry oh Heterocyclic Compounds?(A. Weissberger, ed.), Vol. 17, pp. 245-262. Wiley, New York, 1962. BHAT, B. G., CHANDRASEKHARA, N. Interaction of piperine with rat-liver microssomes. Toxicology 44 (1): 91-98, 1987. BARREIRO, E. J., FRAGA, C. A. M., ARA?JO Jr., J. X. O uso de materias-primas vegetais para a s?ntese de f?rmacos. In: Sim?es, C.M.O. (Ed.) et al., Farmacognosia: da planta ao medicamento, Florian?polis: Ed. Universidade/Ed. Da UFSC: 123-142, 1999. 140 BARRETO, L. M., CARMO, E. H. Determinantes das condi??es de sa?de e problemas priorit?rios no pa?s. In: 11a Confer?ncia Nacional de Sa?de, Dispon?vel no endere?o eletr?nico: http:\\www.datasus.gov.br.1994. BARRETO-JUNIOR, C. B. Abordagem para a s?ntese de amidas naturais bioativas e seus an?logos. Disserta??o de Mestrado, UFRuralRJ, 2005. BAZ?N, P. C. ; LO PRESTI, M. S. ; RIVAROLA, H. W.; TRIQUELL, M. F.; FRETES, R.; FERN?NDEZ, A.; R. ENDERS, J. ;OLIVA, P. Chemotherapy of chronic indeterminate Chagas disease: a novel approach to treatment. Parasitol Res. 103:663?669, 2008. BENLTIFA, M. ; VIDAL, S. ; GUEYRARD, D. 1,3-Dipolar cycloaddition reactions on carbohydrate-based templates: synthesis of spiro-isoxazolines and 1,2,4- oxadiazoles as glycogen phosphorylase inhibitors. Tetrahedron Letters. 47 , 6143? 6147, 2006. BORA, R. O. & FAROOQUI, M. Synthesis os substituted 1,2,4-oxadiazoles from substituted acid chlorides and amidoximes under mild conditions. J. Heterrocyclic Chem. 44, 645, 2007. BOYER, J. H., in ?Heterocyclic Compounds? (R. C. Ederfield, ed.) Vol. 7, pp. 462-540. Wiley, New York, 1962. BRENER, Z., ANDRADE, Z. A. Trypanosoma cruzi e doen?a de Chagas. Guanabara Koogan, Rio de Janeiro, 1979. BREUER, H. Nitroherocycles. I. Nitrofuryl-substituted- 3-amino-1,2,4-oxadiazoles and 5-amino-1,2,4-oxadiazoles. J. Med. Chem. 1969. CHIOU, S. & SHINE, H. J. A simplified procedure for preparing 3,5- disubstituted- 1,2,4-oxadiazoles by reaction of amidoximes with acyl chlorides in pyridine solutions. J. Heterocycl. Chem., 26 (125) 1989. CIAPETTI, P. & GIETHLEN, B. Molecular Variations Based on Isosteric Replacements in Wermuth?s The Practice of Medicinal Chemistry. Cap. 15, 3a Ed. pp. 311-312, 2008. 141 CLAPP, L. B. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: New York,; Vol. 20, pp 65?116, 1976. CONLEY, R. T. & MIKULSKI, F. Abnormal Beckman rearrangements in poliphosphoric acid. 1. Benzil monoximes and related oximes. J. Org. Chem. 24, 97, 1959. CONTRERAS, V. T., SALLES, J. M.. THOMAS, N;. MOREL, C. M. & CHAN. J. H. In vitro differentiation of Trypanosoma cruzi under chemically defined conditions. Mol. Biochem. Parsitol. 16: 315-327, 1985. COSTA, P. R. R. Safrol e eugenol: estudo de reatividade e uso em s?ntese de produtos naturais biologicamente ativos e seus derivados. Qu?mica Nova. 23 (3), 2000. COTTRELL, D.M.; CAPERS, J.; SALEM, M.S.; DeLUCA-FRADLEY, K.; CROFT, S.L.; WERBOVETZ, K.A. Antikinetoplastid activity of aryl-5- thyocyanatomethyl-1,2,4-oxadiazoles, Bioorg. Med. Chem., 12, 2815-2824. 2004. COURA, J. R., DE CASTRO, S. L. A Critical review on Chagas disease chemotherapy. Mem. Inst. Oswaldo Cruz, 97 (1): 3-24, 2002. CORR?A, A. G. Taxol: da descoberta ao uso terap?utico. Quim. Nova, 18: 460-467, 1995. DE ARA?JO-J?NIOR, J. X., DA CUNHA, E. V. L., CHAVES, M. C. O., GRAY, A. I. Piperdardine, a piperidine alkaloid from Piper tuberculatum. Phytochemistry 44(3): 559-561, 1997. D?HOOGE, R., PEI, Y. Q., RAES, A., LEBRUM, P., VANBOGAERT, P. P., DE DEYN, P. P. Anticonvulsant activity of piperine on seizures induced by excitatory amino acid receptor agonists. Arzneim. Forsch./Drug Res. 46 (6): 557-560, 1996. 142 DE PAULA, V. F., BARBOSA, L. C. A., DEMUNER, A. J., VELOSO, D. P., PICAN?O, M. C. Synthesis and inseticidal activity of new amide derivatives of piperine. Pest. Manag. Sci. 56 (2): 168-174, 2000. DIANA, G. D.; VOLKOTS, D. L.; NITZ, T. J.; BAILEY, T. R.; LONG, M. A.; VESCIO, N.; ALDOUS, S.; PEVEAR, D. C.; DUTKO, F. J. Oxadiazoles as Ester Bioisosteric Replacements in Compounds Related to Disoxaril. Antirhinovirus Activity J. Med. Chem. 1994, 37, 2421?2436. DUSCHAK, V.G.;.COUTO, A. S. An Insight on Targets and Patented Drugs for Chemotherapy of Chagas Disease. Recent Patents on Anti-Infective Drug Discovery, 2, 19-51, 2007. ELOY, F. Fortschr. Chem. Fortsch. 4, 807-876, 1965. FERREIRA, W. S. Utiliza??o da piperina como prot?tipo na s?ntese de novos antichag?sicos da classe das 1,3,4-tiadiaz?lio-2- fenilaminas. . Disserta??o de Mestrado, UFRuralRJ, 2005. FERREIRA, W. S.; FREIRE-DE-LIMA, L.; SARAIVA, V. B.; ALISSON-SILVA, F.; MENDON?A-PREVIATO, L.; PREVIATO, J. O.; ECHEVARRIA, A.; LIMA, M. E. F. Novel 1,3,4-thiadiazolium-2-phenylamine chlorides derived from natural piperine as trypanocidal agents: Chemical and biological studies. Bioorg. Med. Chem. 16, 6, 2984-2991. 2008. FREIRE-DE-LIMA, L.; RIBEIRO, T. S.; ROCHA, G. M.; BRAND?O, B. A.; ROMEIRO, A.; MENDON?A-PREVIATO, L.; PREVIATO, J. O.; LIMA, M. E. F.; CARVALHO, T. M.; HEISE, N. The toxic effects of piperine against Trypanosoma cruzi: ultrastrctutal alterations and reversible blockage of cytokinesis in epimastigote forms. Parasitol. Res., 102, 5, 1059-1067. 2008. GADEBUSCH, H. H. ; BREUER, G. L. ; BASCH, H. I. ; SEMAR, R. Antimicrob. Agents Chemother., 280, 1969. 143 GEISLER, J. G., GROSS, G. G. The biosynthesis of piperine in Piper nigrum. Phytochemistry 29 (2): 489-492, 1990. GEISMAN, T. A., CROUT, D. H. G. Organic Chemistry of Secundary Plant Metabolism. Freenar Cooper, San Francisco: 170, 1969. GFESSER, G. A.; ZHANG, H. ; DINGES, J. ; FOX, G. B. ; PAN, J. B. Strcturerelationship of non-imidazole H3 receptor ligands. Part 3: 5-Substituted 3-phenyl- 1,2,4-oxadiazoles as potent antagonists. Bioorg. Med. Chem Lett., 14, 673-676, 2004. GHOSHAL, S., PRASAD, B. N. K., LAKSIMI, V. Antiamoebic activity of Piper longum fruits against Entamoeba histolytica in vitro and in vivo. J. Ethnopharm. 50 (3): 167-170, 1996. HAVENS, C. ; BRYANT, N. ; ASHER, L. ; LAMOREAUX, L. ; PERFETTO, S. ; BRENDLE, J. ; WERBOVETZ, K. Mol. Biochem. Parasitol. 110, 223-236, 2000. HYNES, J. B. & GRATZ, R. F. Hydroxylamine Derivatives as Potential Antimalarial Agents. 3. 1,2,4-Oxadiazoles. J. Med. Chem., 15 , 11, 1198, 1972. HOLTON, R. A., KIM, H. B., SOMOZA, C., LIANG, F., BIEDIGER, R. J., BOATMAN, P. D., SHINDO, M., SMITH, C. C., KIM, S. C., NADIZADEH, H., SUZUKI, Y., TAO, C. L., VU, P., TANG, S. H., ZHANG, P. S., MURTHI, K. K., GENTILE, L. N., LIU, J. H. First total synthesis of Taxol. 2. completion of the Cring and D-ring. J. Am. Chem. Soc. 116 (4): 1597-1598, 1994a. HOLTON, R. A., KIM, H. B., SOMOZA, C., LIANG, F., BIEDIGER, R. J., BOATMAN, P. D., SHINDO, M., SMITH, C. C., KIM, S. C., NADIZADEH, H., SUZUKI, Y., TAO, C. L., VU, P., TANG, S. H., ZHANG, P. S., MURTHI, K. K., GENTILE, L. N., LIU, J. H. First total synthesis of Taxol. 1. functionalization of the B-ring. J. Am. Chem. Soc. 116 (4): 1599-1600, 1994b. IKAN, R. In: Natural Products: A Laboratory Guide, Academic Press, 2nd Edition: 233- 238, 1991. 144 JAKOPIN, Z. ; ROSKAR, R.; DOLENC, M. S. Synthesis of 3,5-disubstituted 1,2,4- oxadiazoles as peptidomimetic building blocks. Tetrahedron Letters. 48, 1465? 1468, 2007. JOHRI, R. K., THUSU, N., KHAJURIA, A., ZUTSHI, U. Piperine-mediated changes in the permeability of rat intestinal epithelial-cells the status of gamma-glutamyl transpeptidase activity, uptake of amino-acid and lipid-peroxidation. Biochem. Pharmacol. 43 (7): 1401-1407, 1992. KAPIL, A. Piperine: a potent inhibitor of Leishmania donovani promastigotes in vitro, Planta Medica, 59: 474, 1993. KOUL, S., KOUL, J. L., TANEJA, S. C., DHAR, K. L., JAMWAL, D. S., SINGH, K., REEN, R. R., SINGH, J. Structure-activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities. J. Bioorg. Med. Chem. 8 (1): 251-268, 2000. KUMAR, D.; PATEL, G.; JOHNSON, E. O. ; SHAH, K. Synthesis and anticancer activities of novel 3,5-disubstituted-1,2,4-oxadiazoles. Bioorganic & Medicinal Chemistry Letters 19 , 2739?2741, 2009. KUSAMA, H., HARA, R., KAWAHARA, S., NISHIMORI, T., KASHIMA, H., NAKAMURA, N., MORIHIRA, K., KUWAJIMA, I. Enationselective total synthesis of (-)-taxol. J. Am. Chem. Soc. 122: 3811-3820, 2000. LEE, S. A., HONG, S. S., HAN, X. H., HWANG, J. S., OH, G. J. LEE, S. K. Peperine from the Fruits of Piper longrum with Inhibitory Effect on Monoamine Oxidase and Antidepressant-Like Activity. Chem. Pharm. Bull. 53 (7): 832-835, 2005. LEE, S. E., PARK, B. S., KIM, M. K., CHOI, W. S., KIM, H. T., CHO, K. Y., LEE, S. G., LEE, H. S. Fungicidal activity of pipernonadine, a piperidine alkaloid derived from long pepper, Piper longum L., against phytopathogenic fungi. Crop. Protec. 20: 523-528, 2001. 145 LIN, Z. X., HOULT, J. R. S., BENNET, D. C., RAMAN, A. Stimulation of mouse melanocyte proliferation by Piper nigrum fruit extract and its main alkaloid, piperine. Planta Medica 65: 600, 1999. LIU, G. Q., ALGERI, S., CECI, A., GARATTINI, S., GOBBI, M., MURAI, S. Stimulation of serotonin synthesis in rat-brain after antiepilepsirine, antiepileptic piperine derivative. Biochem. Pharmacol. 33 (23): 3883-3886, 1984. LEANDRI, G. Boll. Sci. Fac. Chim. Ind. Bologna, 14, 80, 1956. LEWINSONHN, T. M.; PRADO, P. I.; Biodiversidade Brasileira ? S?ntese do Estado Atual do Conhecimento, 1?. ed., Ed. Pinsky: S?o Paulo, 2002, cap. 1, p. 17-25. LEWINSOHN, R. Doen?a de Chagas: paradoxos e ila??es. http://www.comciencia.br/reportagens/2005/06/11.shtml, 2005. LIMA, L. M.& BARREIRO, E. J. Bioisosterism: A useful strategy for molecular modification and drug design. Current Medicinal Chemistry. 12 (1), 23-49, 2005. LIU, G. Q., ALGERI, S., CECI, A., GARATTINI, S., GOBBI, M., MURAI, S. Stimulation of serotonin synthesis in rat-brain after antiepilepsirine, antiepileptic piperine derivative. Biochem. Pharmacol. 33 (23): 3883-3886, 1984. LOMBARDINO, J. G.; LOWE III, J. A. The role of the medicinal chemist in drug discovery - then and now. Nat. Rev. Drug Discov. 3, 853, 2004. LOROSA, E. S.; VALENTE, M. V. M. P. ; VANDA CUNHA, V.; LENT, H.; JURBERG, J. Laborat?rio Nacional e Internacional de Refer?ncia em Taxonomia de Triatom?neos, Departamento de Entomologia Foco de Doen?a de Chagas em Arc?dia, Estado do Rio de Janeiro, Brasil Mem Inst Oswaldo Cruz, Rio de Janeiro, Vol. 98(7): 885-887, 2003 MANN, J.; Murder, Magic, and Medicine, Oxford University Press: Oxford, p. 1-16. 1992. 146 MARCH, J. Advanced Organic Chemistry-Reactions, Mecanism and Structure. John Willey & Sons, 3?ed.: 388, 437, 438, 1095, 1099, 1100 e 1101, 1985. MITSCHER, L. A.; GRACEY, H. E.; CLARK III, G. W.; SUZUKI, T. Quinolone antimicrobial agents. 1. Versatile new synthesis of 1-alkyl-1,4-dihydro-4-oxo-3- quinoline carboxylic acids. J. Med. Chem. 21 (5), 487, 1978. MEDEBIELLE, M.; AIT-MOHAND, S.; BURKHLODER, C.; DOLBIER, W. R., JR.; LAUMOND, G.; AUBERTIN, A.-M. Syntheses of new diflouromethylene bezoxazole and 1,2,4-oxadiazole derivatives, as potent non-nucleoside HIV-1 reverse transcriptases inhibitors. J. Fluorine Chem. 2005, 126, 535?542. NEWMANN, H. Photochemistry of 3,5-diphenyl-1,2,4-oxadiazole. 2. Photolysis in aprotic media. Tetrahedron Lett. 20, 2421, 1968. NEWMAN, D. J., CRAGG, G. M., SNADER, K. M. Natural Products as Sources of New Drugs over the Period 1981-2002. J. Nat. Prod. 66: 1022-1037, 2003. NICOLAIDES, D. N.;. FYLAKTAKIDOU K. C., KONSTANTINOS E. LITINAS, K. E.; HADJIPAVLOU-LITINAB, D. Synthesis and biological evaluation of several coumarin-4-carboxamidoxime and 3-(coumarin-4-yl)-1,2,4-oxadiazole derivatives. Eur. J. Med. Chem. 33, 715-724,1998. NICOLAOU, K. C., YANG, Z., LIU, J. J., UENO, H., NANTERMET, P. G., GUY, R. K., CLALBORNE, C. F., RENAUD, J., COULADOUROS, E. A., PAULVANNAN, K., SORENSEN, E. Total sintesis of Taxol. Nature 367: 630- 634, 1994. OLENSEN, P.H.; TONDER, J.E.; HANSEN, J.B.; HOLER, C.H.; RIMVALL, K. Bioisosteric replacement strategy for the synthesis of 1-azacyclic compounds with high affinity for the central nicotinic cholinergic receptors. J. Bioorg. Med. Chem. 8, 1443-1450. 2000. 147 OOI, N. S. & WILSON,. S. Formation and thermal reaction of O-(N-acetylbenzimidoyl) bezamidoxime. Comparison with the formation of 3,5-disubstituted 1,2,4- oxadiazole from O-acetylarylamidoximes and aroylamidoximes. J. Chem. Soc., Perkin Trans. 2, 12,1792, 1980. OUTIRITE, M.; LEBRINI, M. ; BENTISS, F. New one step synthesis of 3,5- disubstituted 1,2,4-oxadiazoles. J. Heterocyclic Chem. 44, 1529, 2007. PARK I.K., LEE S.G., SHIN S.C., PARK J.D., AHN Y.J. Larvicidal activity of isobutylamides identified in Piper nigrum fruits against three mosquito species, J. Agric. Food Chem., 50 (7), 1866-1870, 2002. PARMAR, V. S., JAIN, S. C., BISHT, K. S., JAIN., TANEJA, P., JHA, A., TYAGI, O. D., PRASAD, A. K., WENGEL, J., OLSEN, C. E., BOLL, P. M. Phytochemistry of the genus Piper. Phytochemistry 46 (4): 597-673, 1997. PARMAR, V. S., JAIN, S. C., GUPTA, S., TALWAR, S., RAJWANSSHI, V. K., KUMAR, R., AZIM, A., MALHOTRA, S., KUMAR, N., JAIN, R., SHARMA, NN. K., TYAGI, O. D., LAWRIE, S. J., ERRINGTON, W., HOWART, O. W., OLSEN, C. E., SINGH, S. K., WENGEL, J. Polyphenols and alkaloids from Piper species. Phytochemistry 49 (4): 1069-1078, 1998. PERRIN, D. D.; ARMAREJO, W. L. F.; PERRIN, D. R. Purification of Laboratory Chemicals. Pergamon Press. 1966. PISSINATE, K. Atividade citot?xica de Piper nigrum e Struthanthus marginatus. Estudo preliminar da correla??o entre a citotoxicidade e hidrofobicidade da piperina e derivados sint?ticos. Disserta??o de mestrado, UFRuralRJ, 2006. RASCADO, M. F. N. Utiliza??o do safrol na s?tese de derivados do n?cleo pirroloquinolina, potencialmente ?teis como antineopl?sicos. Disserta??o de Mestrado, UFRuralRJ, 1997. RAAY, B., MEDDA, S., MUKHOPADHYAY, S., BASU, M. K. Targetin of piperine intercalated in mannose-coated liposomes in experimental leishmaniasis. Indian J. Biochem. Biophamacol. 36 (4): 248-251, 1999. 148 REEN, R. K., WIEBEL, F. J., SINGH, J. Piperine inhibits aflatoxin B-1-induced cytotoxity and genotoxicity in V79 Chinese hamster cells genetically engineered to express rat cytochrome P4502B1. J. Ethnopharm. 58 (3): 165-173, 1997. RIBEIRO, T. S.; FREIRE-DE-LIMA, L.; PREVIATO, J. O.; MENDON?APREVIATO, L.; HEISE, N.; LIMA, M. E. F. Toxic effects of natural piperine and tis derivates on epimastigotes and amastigotes of Trypanosoma cruzi. Biorg&Med. Chem. Letts. 14, 3555-3558, 2004. RIBEIRO, T. S., Transforma??es qu?micas no alcal?ide natural piperina e avalia??o da atividade t?xica sobre Trypanosoma cruzi. Disserta??o de Mestrado, UFRuralRJ, 2004. RODIG, O. R., BELL-JR, D. E., CLARK, A. K., Organic Chemystry Laboratory, Standard & Microscale Experiments. Saunders College Publishing, 215, 1990. SANTOS, A. P. Piperina: Modifica??es Estruturais, S?ntese de an?logos e Avalia??o Citot?xica. Disserta??o de Mestrado, UFRuralRJ, 1999. SCHMUNIS, G. A. A tripanossom?ase americana e seus impactos na sa?de p?blica das Am?ricas. In: BRENER, Z., ANDRADE, Z. A., BARRAL-NETO, M. (eds). Trypanosoma cruzi e Doen?a de chagas. Rio de Janeiro: Guanabara Koogan, 2a ed. Cap. 1, 2000. SCHMUNIS, G. A. Epidemiology of Chagas disease in non endemic countries: the role of international migration Pan American Health Organization/World Health Organization, 525 23rd Street, NW Washington, DC 20037, US. Mem Inst Oswaldo Cruz, Rio de Janeiro. 2007. SCOTT, W. P., MCKIBBEN, G. H. Toxicity of black pepper extract to boll weevils. J. Econ. Entomol. 71 (2): 343-344, 1978. SHOBA, G., JOY, D., THANGAM, J., MAJEED, M., RAGENDRAN, R., SRINIVAS, P. S. R. Influence of piperine on the pharmacokinetics of curcumin in animals and human volunteers. Planta Medica 64 (4): 353-356, 1998. 149 SEMLER, U., GROSS, G. G. Distribution of piperine in vegetative perts of Piper nigrum. Phytochemistry 27 (5): 1566-1567, 1988. SILVA, E. F., CANTO-CAVALHEIRO, M. M., BRAZ, V. R., CYSNEFINKELSTEIN, L., LEON, L. L., ECHEVARRIA, A. Synthesis and biological evaluation of new 1,3,4-thiadiazolium-2-phenylamine derivatives against Leishmania amazonensis promastigotes and amastigotes.. Eur. J. Med. Chem. 37: 979-984, 2002. SONDENGAM, B. L. Organic and Bio-Organic Chemistry. J. Chem. Soc., Perkin Transations 1 (6): 1219-1221, 1983. SRIVASTAVA, R.M., BRINN. I.M., MACHUCA-HERRERA, J.O., FARIA, H.B., CARPENTER. J.B., ANDRADE, D., VENKATESH, C.G., MORAIS, L.P.F. Benzamidoximes: structural, conformation and spectroscopic studies. I J. Molecular Structure. 406, 159-167, 1997. SRIVASTAVA, R. M.; LIMA, A. A.; VIANA, O. S. Antiinflammatory Property of 3- Aryl-5-(n-propyl)- 1,2,4-oxadiazoles and Antimicrobial Property of 3-Aryl-5- (npropyl)- 4,5-dihydro-1,2,4-oxadiazoles:Their Syntheses and Spectroscopic Studies. Bioorganic & Medicinal Chemistry, 11, 1821?1827, 2003. SRIVASTAVA, R.M. Mass spectrometric analysis of 1,2,4-oxadiazoles and 4,5- dihydro-1,2,4-oxadiazoles. Mass Spectrometric Reviews, 24, 328-346, 2005. SUNILA, E. S., KUTTAN, G. Immunomodulatory and antitumor activity of Piper longum L. and piperine. J. Ethnopharm. 90: 339-346, 2004. TIEMANN, F.& KRUGER, P. Ber. 17, 1685, 1884. TROUILLER, P., OLLIARO, P., TORREELE, E., ORBINSKI, J., LAING, R., FORD, N. Drug development for neglected diseases: a deficient market and a publichealth policy failure. The Lancet. 359, 2002. URBINA, J. A. Chemotherapy of Chagas? disease: the how and the why. J. Mol. Med. 77:332?338, 1999. 150 URBINA, J. A. & DOCAMPO, R. Specific chemoteraphy og Chagas disease: controversies and advances. Trends in Parasitology. Vol. 19, No 11, 2003. VELLAICHAMY, L.; BALAKRISHNAN, S.; PANJAMURTHY, K.; MANOHARAN, S.; ALIAS, L. M. Chemopreventive potential of piperine in 7,12-dimethylbenz[a]anthraceneinduced skin carcinogenesis in Swiss albino mice. Environmental Toxicology and Pharmacology 28, 11?18, 2009. VENKATASAMY, R., FAAS, L., YOUNG, A. R., RAMAN, A., HIDER, R. C. Effects of piperine analogues on stimulation of piperine analogues on stimulation of melanocyte proliferation and melanocyte differentiation. Bioorg. Med. Chem. 12: 1905-1920, 2004. VIEGAS, C. J., DA SILVA, V. B. Os Produtos Naturais e a Qu?mica Medicinal Moderna. Quim. Nova 29 (2): 326-337, 2006. YUNES, R. A., PEDROSA, R. C., CECHINEL FILHO, V., F?rmacos e fitoter?picos: A necessidade do desenvolvimento da ind?stria de fitoter?picos e fitof?rmacos no Brasil. Quim. Nova 24 (1): 147-152, 2001. WEISSMANN, G. Aspirin. Sci. Am. 264 (1): 84-90, 1991 WHO-World Health Organization, Chagas disease: Thirteenth Programme Report, UNDP/TDR, Geneve 1997. WHO-World Health Organization. Tech. Rep. Ser. , 905, 1, 2002 ZAVITZ, K. H.; BARTEL, P. L.; HOBDEN, A. N. Drug targets, target identification, validation and screening in Wermuth?s The Practice of Medicinal Chemistry. Cap. 5, 3a Ed. pp. 118, 2008. |
Page generated in 0.0053 seconds