1. TEDE
  2. CAMPUS SEROPÉDICA
  3. Programa de Pós-Graduação em Química
  4. Mestrado em Química
???item.export.label??? ???item.export.type.endnote??? ???item.export.type.bibtex???

Please use this identifier to cite or link to this item: https://tede.ufrrj.br/jspui/handle/jspui/2077
Full metadata record
DC FieldValueLanguage
dc.creatorZampirolli, Leticia Silotti-
dc.creator.Latteshttp://lattes.cnpq.br/0235373064063651por
dc.contributor.advisor1Costa, João Batista Neves da-
dc.contributor.advisor1Latteshttp://lattes.cnpq.br/8678051184959173por
dc.contributor.referee1Marques, Monica Regina da Costa-
dc.contributor.referee2Bernardino, Alice Maria Rolim-
dc.contributor.referee3Rumjanek, Victor Marques-
dc.date.accessioned2017-10-05T11:53:08Z-
dc.date.issued2009-05-27-
dc.identifier.citationZAMPIROLLI, Leticia Silotti. Dialquilfosforilidrazonas derivadas de isatinas N - substituídas com potencial atividade biológica. 2009. 256 f. Dissertação (Mestrado em Química) - Instituto de Ciências Exatas, Universidade Federal Rural do Rio de Janeiro, Seropédica - RJ, 2009.por
dc.identifier.urihttps://tede.ufrrj.br/jspui/handle/jspui/2077-
dc.description.resumoUma série de 16 dialquilfosforilidrazonas (ácido fosforoidrazídico, N’ -[1,2-diidro-2-oxo-(R1)- 3H- indol-3-ilideno] -, éster de dialquila), sendo todas inéditas, foram sintetizadas e caracterizadas pelas técnicas de espectrometria de IV, RMN de 1H, RMN de 13C, RMN de 31P e massas. As novas dialquilfosforilidrazonas foram sintetizadas em três etapas de reação. A primeira etapa consistiu na síntese de diferentes fosfitos de dialquila que foram obtidos através da reação do tricloreto de fósforo (PCl3) com três mols do álcool correspondente. Na segunda etapa, a reação dos fosfitos de dialquila com a hidrazina, em um sistema bifásico, levou á formação das dialquilfosforilidrazinas. A última etapa foi a condensação destas dialquilfosforilidrazinas com diferentes isatinas substituídas. A análise dos espectros de RMN de 1H, RMN de 13C, RMN de 31P das dialquilfosforilidrazonas mostraram a coexistência dos dois possíveis diastereoisômeros E e Z, para os compostos 1, 2, 6, 10 e 12, enquanto que para os compostos restantes observou-se apenas o diastereoisômero Z. Dos compostos sintetizados, dez foram avaliados preliminarmente quanto ao potencial inibitório de proliferação de dois protozoários (Trypanosoma cruzi e Leishmania amazonensis). Para Leishmania amazonensis todos os compostos testados apresentaram inibição da proliferação celular de 98 % a 50 μM. Enquanto que para T.cruzi verificou-se inibição da proliferação celular de epimastigotas superior a 75% para todos compostos testados, a exceção do composto (6) cuja inibição foi de 59 %. Esses dez compostos também foram avaliados frente ao protozoário Plasmodium falciparum apresentando inibição superior a 90 % para todos os compostos testados, a uma concentração de 1mM. Essas dialquilfosforilidrazonas também tiveram a ação fungicida avaliada frente aos fungos fitopatogênicos (Rhizoctonia solani e Fusarium oxysporum). Em Rhizoctonia solani os compostos (9) e (11) apresentaram inibição do crescimento miscelial de 58 %, já o composto (12) apresentou inibição de 72%. Para o Fusarium oxysporum destacaram-se os compostos (1, 2, 11 e 12) com inibição superior a 52 %. Esses compostos também foram avaliados quanto ao potencial inibitório de germinação em sementes de alface e verificouse que os mesmos compostos que apresentaram efeitos fungistáticos, não inibiram a germinação de sementes de alface.por
dc.description.abstractA series of new dialkylphosphorylhydrazones (phosphorohydrazidic acid, N’-[1,2-dihydro-2- oxo-(R1)-3H-indole-3-iliden]- dialkyl esters was synthesized and characterized by IR, 1H, 13C and 31P NMR and mass spectroscopy. These dialkylphosphorylhydrazones were synthesized in three steps. The first step involved the synthesis of different dialkylphosphites which are obtained by the reaction of PCl3 with three mols of the corresponding alcohols. The second step consisted of the reaction between the dialkylphosphites and hydrazine in a two phase system, leading to the formation of the dialkylphosphorylhydrazines. Finally, the last step was the condensation of these dialkylphosphorylhydrazines with different N-substituted isatins. The analysis of the 1H, 13C and 31P NMR spectra showed the existence of the two possible diastereoisomers E and Z for compounds 1, 2, 6, 10 and 12, while for the remaining compounds only the Z isomer is present. Ten of these compounds were preliminarily tested for their inhibition potential against two protozoa (Trypanosoma cruzi and Leishmania amazonensis). All compounds tested showed cell proliferation inhibition of 98% at 50 μM for Leishmania amazonensis, whereas for T. cruzi, inhibition of epimastigote cell proliferation was found to be higher than 75% for all compounds tested except 6, which showed a 59% inhibition. These ten compounds were also evaluated against Plasmodium falciparum, affording inhibitions higher than 90% for a 1mM concentration. These compounds were also investigated for their fungicidal activity against phytopatogenic Rhizoctonia solani and Fusarium oxysporum. Compounds 9 and 11 showed a miscelial growth inhibition of 58% for Rhizoctonia solani while compound 12 afforde a 72% inhibition. Compounds 1, 2, 11 and 12 gave Fusarium oxysporum inhibition higher than 52%. Finally, the compounds synthesized were also evaluated for their inhibitory potential against lettuce seed germination and it was observed that the same compounds which showed fungicidal activity were not able to inhibit seed germination.eng
dc.description.provenanceSubmitted by Sandra Pereira (srpereira@ufrrj.br) on 2017-10-05T11:53:08Z No. of bitstreams: 1 2009 - Leticia Silotti Zampirolli.pdf: 25893124 bytes, checksum: bd44115917dd331e511dc65cd22738a1 (MD5)eng
dc.description.provenanceMade available in DSpace on 2017-10-05T11:53:08Z (GMT). No. of bitstreams: 1 2009 - Leticia Silotti Zampirolli.pdf: 25893124 bytes, checksum: bd44115917dd331e511dc65cd22738a1 (MD5) Previous issue date: 2009-05-27eng
dc.description.sponsorshipCoordenação de Aperfeiçoamento de Pessoal de Nível Superior, CAPES, Brasil.por
dc.formatapplication/pdf*
dc.thumbnail.urlhttps://tede.ufrrj.br/retrieve/5999/2009%20-%20Leticia%20Silotti%20Zampirolli.pdf.jpg*
dc.thumbnail.urlhttps://tede.ufrrj.br/retrieve/15270/2009%20-%20Leticia%20Silotti%20Zampirolli.pdf.jpg*
dc.thumbnail.urlhttps://tede.ufrrj.br/retrieve/21788/2009%20-%20Leticia%20Silotti%20Zampirolli.pdf.jpg*
dc.thumbnail.urlhttps://tede.ufrrj.br/retrieve/28172/2009%20-%20Leticia%20Silotti%20Zampirolli.pdf.jpg*
dc.thumbnail.urlhttps://tede.ufrrj.br/retrieve/34550/2009%20-%20Leticia%20Silotti%20Zampirolli.pdf.jpg*
dc.thumbnail.urlhttps://tede.ufrrj.br/retrieve/40938/2009%20-%20Leticia%20Silotti%20Zampirolli.pdf.jpg*
dc.thumbnail.urlhttps://tede.ufrrj.br/retrieve/47294/2009%20-%20Leticia%20Silotti%20Zampirolli.pdf.jpg*
dc.thumbnail.urlhttps://tede.ufrrj.br/retrieve/53716/2009%20-%20Leticia%20Silotti%20Zampirolli.pdf.jpg*
dc.languageporpor
dc.publisherUniversidade Federal Rural do Rio de Janeiropor
dc.publisher.departmentInstituto de Ciências Exataspor
dc.publisher.countryBrasilpor
dc.publisher.initialsUFRRJpor
dc.publisher.programPrograma de Pós-Graduação em Químicapor
dc.relation.referencesAINSCOUGH, E.W.; BRODIE, A.M.; DOBBS, A.J.; RANFORD, J.D.; WATERS, J.M. Antitumour Copper (II) Salicylaldehyde Benzoylhydrazone (H2sb) Complexes: Physicochemical Properties and the Single-Crystal X-Ray Structures of [{Cu(H2sb) (CCl3CO2)2}2] and [{Cu(H2sb) (ClO4) (C2H5OH)}2] and the Related Salicylaldehyde Acetylhydrazone (H2sa) Complex, of [Cu(Hsa) Cl(H2O)]. H2O. Inorganica Chimica Acta. v. 267, p. 27-38, 1998. ALVAR, J.; CANAVATE, C.; GUTIÉRREZ-SOLAR, B.; JIMÉNEZ, M.; LAGUNA, F.; LÓPEZ-VÉLEZ, R.; MOLINA, R.; MORENO, J. Leishmania and human immunodeficiency vírus coinfection: the first 10 years. Clin. Microbiol. Rev. v.10, p. 298- 319, 1997. ALDRIDGE, W. N. & REINER, E. Enzyme inhibitors as substrates. Interation of esterases with esters of organophosphorus and carbamic acids. In Frountiers of biology (A Neuberger and E. L. Tatum, Eds). North-Holland, Amsterdam. v. 26, 1976. ARMIJOS, R. X.; WEIGEL,M.M.; HIDALGO, A.; CEVALLOS, W.; CORREA, J. Safety, immunogenicity, and efficacy of na autoclaved Leishmania amazonensis vaccine plus BCG adjuvant against New World cutaneous leishmaniasis. Vaccine.v. 22, p. 1320-1326, 2004. ARSENIJEVIC, L.; BOGAVAC, M.; PAVLOV, S; ARSENIJEVIC, V. Reduction of the carbonyl groups of N-alkylisatin with zinc in na aprotic solvent. Arh. Farm. v. 35, p. 1-2, n. 39, 1985. ARBUZOV, A. E.; Phys. Chem. Soc. v. 38, p. 687, 1906. ATHERTOON, F. R. OPENSHAW, H. T. & TODD, A. R. Studies on phophorylation. Further studies on the use of dibenzyl chlorophosphonate and the examination of certain alternative. J. Chem. Soc. p. 660, 1945. BARREIRO, E.J.; GASTON, M.A.; DIAS, L.R.S.; FREITAS, A.C.C.; MIRANDA, A.L.P. Synthesis and Analgesic Properties of New 4-arylhydrazone 1-H pyrazole [3,4-b] pyridine Derivatives. Pharm. Acta Helv. v. 71, p. 213-219, 1996. BARREIRO, E.J.; FRAGA, C.A.M.; MIRANDA, A.L.P.; RODRIGUES, C.R. A Química Medicinal de N-Acilidrazonas: Novos Compostos-Protótipos de Fármacos Analgésicos, Antiinflamatórios e Anti-Trombóticos. Química Nova. v. 25, n. 1, p. 129-148, 2002. BARREIRO, E.J.; MIRANDA, A.L.P.; LIMA, P.C.; LIMA, L.M.; da SILVA, K.C.M.; LÉDA, P.H.O.; FRAGA, C.A.M. Synthesis and Analgesic Activities of Novel NAcylarylhydrazones and Isosters, Derived from Natural Safrole. European Journal of Medicinal Chemistry. v. 35, p. 187-203, 2000. BATTACHARYA, L. K. & THYAGARAJAN, G. The Michaelis-Arbuzov Rearrangement. Chem. Rev.v. 81, p. 415, 1981. BEDENDO, I.P. Parte X: Grupos de Doenças. In: A.BERGAMIN FILHO; H. KIMATI; L. AMORIM. Manual de Fitopatologia: Princípios e Conceitos. 3 ed. Ceres, São Paulo v.1, p. 805-907, 1995 BERGMAN, J; ENGELHARDT, P; KISS, A. I; LINDSTROM, J. O; WARNMARK, K. Ring expansions of N-acylisatins to N-oxidoquinazoline-4-carbohydroxamic acid derivatives induced by hydroxylamine. Studies Org. Chem.: Chem. Heterocycl. Compd. v. 35, p.1, 1988. 111 BERGMAN, J; LINDSTORM, J.O; TILSTAM, U. The structure and properties of some indolic constituents in Couroupita guianensis Aubl. Tetrahedron. v. 41, n. 14, p. 2879- 2881, 1985. BOECHAT, N. e Pinto, A. C. Preparation of, -difluorophenylacetates and - phenylacetamides as analgesics and antiinflammatories. US6034266, p. 9, 2000. CARBRIDGE, P.E.C. The Structural Chemistry of Phosphorus. Elsevier Scientific Publishing, N.Y. 203, 1974. CADOGAN, J. I. G., Organophosphorus Reagentes in Organic Synthesis. Academic Press Inc. (London) LTD. 1st Ed., 1979. CAIXEIRO, J.M.R.; Tese de Doutorado, Universidade Federal Rural do Rio de Janeiro, 2007. CARLTON, F.B.; SIMPSON, W.M. & HADDAD, L.M. The Organophosphate and Other Insecticides. Clinical Management of Poisoning and Drug Overdose, Philadelphia, Pensylvania, USA. WB Saunders Company, 3a ed, p. 836-850, 1998. CASEY, L. A; GALT, R; PAGE, M. I. The mechanisms of hydrolysis of the -lactam isatin and its derivatives. J. Chem. Soc. Perkin Trans. v. 2, n. 1, p. 23, 1993. CHIBALE, K; CHIYANZU, I MCKERROW, J. H; HANSELL, E ROSENTHAL, P.J; GUT, J. Synthesis and Evaluation of Isatins and Thiosemicarbazone Derivatives against Cruzain, Falcipain-2 and Rhodesain. Bioorganic & Medicinal Chemistry Letters. v. 13, p. 3527-3530, 2003. CHIBALE, K.; CHIYANZU, I.; CLARKSON, C.; SMITH, P. J.; LEHMAN, J.; GUT, J. e ROSENTHAL, P. J. Design, synthesis and anti-plasmodial evaluation in vitro of new 4- aminoquinoline isatin derivatives. Bioorg. Med. Chem. v. 13, n. 9, p. 3249, 2005. CIA, E.; SALGADO, C. L. Doenças do algodoeiro. In: KIMATI, H.; AMORIM, L.; BERGAMIN FILHO, A.; CAMARGO, L.E.A.; REZENDE, J. A. M. Manual de Fitopatologia: Doenças das plantas cultivadas. v. 2, p. 33-48, 1997. COOK, R. J. Management of the associated microbiota. Plant Disease. v. 1, p. 145-166. COFFEY, S. Rood's Chemistry of Carbon Compounds, 2nd ed., Elsevier Publishing Company: London, 1965. CORNFORTH, J. W. Structures of isamic acid and methylisatoid. J. Chem. Soc. Perkin Trans. v. 19, p. 2004, 1976. COSTA, P.; PILLI, R.; PINHEIRO, S.; VASCONCELLOS. Substâncias Carbonilados e Derivados. Artmed Editora S A Subdivisão Bookman Companhia Editora. Série Química Orgânica. 2003. COTTON, F. A. Advanced Inorganic Chemistry. In: USA. 5th Ed. John Wiley and Sons. 1988. COTTON, F. A. & SCHUNN, P. A. J. Am. Chem. Soc. v. 85, p. 2394, 1963. COURA, J. R.; DE CASTRO, S. L. A Critical review on Chagas disease chemotherapy. Mem. Inst. Oswald Cruz. v. 97. n. 1 p. 3-24, 2002. CROFT, S. L.; YARDLEY, V. Chemotherapy of leishmaniasis. Curr. Pharm. Des. v. 8, p. 319-342, 2002. 112 CROFT, S. L. Neglected diseases: progress in drug development. Curr. Opin. Investing. Drugs. v. 8, p. 103-104, 2007. CROFT, S. L.; COOMBS, G. H. Leishmaniasis-current chemotherapy and recent advances in the search for novel drugs. Trends Parasitol. v. 19, p. 502-508, 2003. CROFT, S. L.; BARRETT, M. P.; URBINA, J. A. Chemotherapy of trypanosomiases and leishmaniasis. Trends Parasitol. v. 21, p. 508-512, 2005. CROFT, S. L. Monitoring drug resistance in leishmaniasis. Trop.Med. Int. Health. v. 6, p. 899-905, 2001. DaCOSTA, J. B. N.; Tese de Doutorado, Universidade Federal Rural do Rio de Janeiro, Brasil, 1996. DaCOSTA, J.B.N.; RODRIGUES, J.M.; DONNICI, C.L.; SANTOS dos, V.M.R. Compostos Organofosforados Pentavalentes: Histórico, Métodos Sintéticos de Preparação e Aplicações como Inseticidas e Agentes Antitumorais. Química Nova. v. 30, n. 1, p. 159- 170, 2007. DAVIDSON, R. N. AIDS and leishmaniasis. Genitourin. Med. v. 73, p. 237-239. DAVIES, C. R.; KAYE, P.; CROFT, S. L.; SUNDAR, S. Leishmaniasis: new approaches to disease control. BMJ. v. 326, p. 77-82, 2003. DE SOUZA, S. P. L.; DA SILVA, J. F. M.; DE MATTOS, M. C. S. Heterocycl. Commun. v. 9, p. 31, 2003. DNDi – Drugs for Neglected Diseases initiative, 2008. Disponível em: <http://www.dndi.org/>. Acessado em: 16 Jan 2008. DOS SANTOS,V. M. R.; Tese de Doutorado, Universidade Federal Rural do Rio de Janeiro, Brasil, 1996. ECOBICHON, D. J. Toxic Effects of Pesticides. InCasarett and Doill’s Toxicology. 5th ed., (C.D. Klaussen, Ed). p. 643-698. NY. ETO, M. Organophosphorus Pesticides: Organic and Biological Chemistry, 1st ed., CRC Press: Fukuoka, Japan, 1974. FERNANDES, C.; LEITE, R.S.; LANÇAS, F.M. Bisfosfonatos: Síntese, Análises Químicas e Aplicações Farmacológicas. Química Nova. v. 28, n. 2, p. 274-280, 2005. FISHER, E. B.; VAN WAZER, R, J. R. Use of Organic in phosphorus compounds and its compounds. Interscience: New York, vol. 2, p. 1961, 1897. FORD MOORE, A. H.; PERRY, B. J.; Org. Syn. Coll. v. 4, p. 955, 1963. GAETA, F. C. A.; GALAN, A. A. e KRAYNACK, E. A. Preparation of isatin derivatives as telomerase inhibitors and anticancer agents. PCT Int. Appl. WO9965875, p. 56, 2000. GALLO, M & LAWRYK, N. Organic Phosphorus Pesticides. In HAYES, W.J, LAWS, E. R. Handbook of Pesticide Toxicology. San Diego, California, USA. Academic Press, Inc., v. 2, p. 917-1124, 1991. GARDEN, S. J.; TORRES, J. C.; SILVA, L. E; PINTO, A. C. A convenient methodology for the N-alkylation of isatin compounds. Synth. Commun. v. 28, n. 9, p. 1679, 1998. GEARY, T. G.; EDGAR, A.; JENSEN, J. B. Leishmaniasis – current treatment. In: CAMPBELL, W. C. e REW. R. S (eds). Chemoterapy of Parasitic Diseases. New York: Plenum Press, p. 209-238, 1989. 113 GOULART, A. C. P. Doenças associadas às sementes. Correio Agrícola, janeiro-junho, p. 12-15. GOES, A. J. S.; TENÓRIO, R. P.; LIMA, J.G.; FARIA, A.R.; ALVES, A.J.; AQUINO, T.M. Tiossemicarbazonas: Métodos de Obtenção, aplicações sintéticas e importância biológica. Química Nova. v. 28, n. 6, p. 1030-1037, 2005. GUO, Y.; CHEN, F. TLC-UV-spectrophotometric and TLC-scanning determination of isatin in leaf of Isatis. Zhongcaoyao. v. 17, p. 8-11, 1986. HAENSEL, W. 4-(5-Hydroxy-4-pyrazolylimino)-2-pyrazolin-5-ones and their metal chelates, I. Synthesis of 4-(5-hydroxy-4-pyrazolylimino)-2-pyrazolin-5-ones (rubazoic acids) and compounds with analogous structures. Justus Liebigs Ann. Chem. n. 7/8, p. 1380, 1976. HAUPT, E. T. K. & TOM DICK, H. Phosphorus and Sulfur. v. 27, p. 285, 1986. HERWALDT, B. L. Leishmaniasis. Lancet, v.354, p. 1191-1199, 1999. JENSEN, B. S.; JORGENSEN, T. D.; AHRING, P. K.; CHRISTOPHERSEN, P.; STROBAEK, D.; TEUBER, L. E OLESEN, S. P. Use of isatin oxime derivatives as ion channel activating agents. PCT Int. Appl. WO0033834, p. 49, 2000. JUANG, S. H.; CHEN, L. R.; WANG, Y. C.; LIN, Y. W.; CHOU, S. Y.; CHEN, S. F.; LIU, L. T.; WU, Y. T.; KUO, C. J.; CHEN, T. S. S. Synthesis and evaluation of isatin derivatives as effective SARS coronavirus 3CL protease inhibitors. Bioorg. Med. Chem. Lett., v. 15, n.12, p. 3058, 2005. KARCZMAR, A. Invited Review: Anticholinesterases: dramatic aspects of their use and misuse. Neurochem. Int. v. 32, p. 401-411, 1997. KERTESZ, M. A.; COOK, A.M. & LEISINGER, T. Microbiology Reviews.v. 15, 195-215, 1994. KELSEY, R. G. & LOCKEN, L. Phytotoxic properties of cnici, a Sesqueterpene lactone from Centaura maculosa (Spotted Knapweed). Journal of Chemical Ecology. v.13, p. 19- 33, 1982. KITAEV,Yu.P.; BUZYKIN, B.I.; TROEPOL’SKAYA, T.V. The Structure of Hydrazones. Russian Chemical Reviews. v. 39, n. 6, p. 441-456, 1970. KITAEV,Yu.P.; BUZYKIN, B.I. The Reactions of Hydrazones. Russian Chemical Reviews. v. 41, n. 6, p. 495-515, 1972. KONTECKA, E. G.; SILVAGNI, R.; LIPINSKI, R.; LECOUVEY, M.; MARINCOLA, F. C.; CRISPONI, G.; NURCHI, V. M.; LEROUX, Y.; KOZLOWSKI, H.; Inorg. Chim. Acta, 339, 111, 2002. KOSALOPOFF, G.M.; MAIER, L. Organic Phosphorus Compounds. Wiley – Interscience, N.Y. v. 5, 1973. KUSSEINOV, K. Unsaturated isatin derivatives. Dokl. Akad. Nauk Tadzh. SSR. v. 19, p. 30-32, 1976. LANG, W & KRUEGER, B. Uber ester der Monofluorphosphorsaure. Chem. Ber. 65: 1598. LIU, J.; OLIVIER, K. & PODE, N. C. Toxicology and Applied Pharmacology. v. 158, p.186-196, 1999. 114 LOLOIU, G; MAIOR, O. Isatin chemistry. Synthesis of N-methyl-2,3-dioxo-2,3- dihydropyrrolo[2,3-b]phenoxatiin. Rev. Roum. Chim. v. 42, n.1, p.67, 1997. MAGILL, A. J.; GROGL, M.; GASSER, R. A.; SUN, W.; OSTER, C. N. Visceral infection caused by Leishmania tropica in veterans of Operation Desert Storm. N. Engl. J. Med. v. 328, p. 1383-1387, 1993. MATTOS, M.C.S; ESTEVES, P.M; MENDONÇA, G. F; MAGALHÃES, R.R. Tricholoroisocyanuric Acid in H2SO4: Na Efficient Superelectrophilic Reagent for Cholorination of Isatin and Benzene Derivatives. J. Braz. Chem. Soc. v. 16, n. 4, p.695- 698, 2005. MMV – Medicines for Malaria Venture, 2008. Disponível em: <http://www.mmv.org/>. Acessado em: 16 Jan 2008. MARK, V. Mech. Mol. Migr. v.2, p. 319, 1969. MARTIN, M. B.; GRIMLEY, J. S.; LEWIS, J. C.; HEATH, H. T.; BAILEY, B. N.; KENDRICK, H.; YARDLEY, V.; CALDERA, A.; Lira, R.; URBINA, J. A.; MORENO, S. N. J.; DOCAMPO, R.; CROFT, S. L.; OLDFIELD, E. Bisphosphonates Inhibit the Growth of Trypanosoma brucei, Trypanosoma cruzi, Leishmania donovani, Toxoplasma gondii, and Plasmodium falciparum: A Potential Route to Chemotherapy. J. Med. Chem. v. 44, p. 909, 2001. MICHAELIS, A. E.; KAEHNE, R. Chem. Ber. Stsch. Ges. v. 31, p. 1048, 1898. MICHAELIS, A.; BECKER, T. Ber. Stsch. Chem. Ges. v. 30, p.1003, 1897. MILESON, B. E.; CHAMBERS, J. E.; CHEN, W. L.; EHRICH, M.; ELDEFRAWI, A. L.; GAYLOR, D. W.; HARMENICK, K.; HODGSON, E.; KARCZMAR, A. G.; PADILHA, S.; PODE, C. N.; RICHARDSON, R. J.; SAUNDERS, D. R.; SHEETS, L. P.; SULTATOS, L. G. & WALLECE, K. B. Common Mechanism of Toxicity: A Case Study of Organophosphorus Pesticides. Toxicolo. Sci. v. 41, p. 8-20, 1998. MOPAC2009, JAMES J. P. STEWART, Stewart Computational Chemistry, Colorado Springs, CO, USA, HTTP://OpenMOPAC.net (2008). MONCAYO, A. Chagas disease: current epidemiological trends after the interruption of vectorial and transfusional transmission in the Southern Cone countries. Mem. Inst. Oswaldo Cruz, v. 98, p. 577-591, 2003. MONCAYO, A.; ORTIZ YANINE, M. I. An update on Chagas disease (human American trypanosomiasis). Ann. Trop. Med. Parasitol. v. 100, p. 663-677, 2006. MURRAY, H. W. BERMAN, J.; DAVIES, C.; SARAVIA. Advances in leihmaniasis. Lancet, v. 366, p. 1561-1577, 2005. NAMBA, T.; NOLTE, C.T.; JACKREL, J.; GROB, D. Poisoning Due to Organophosphate Insecticides: Acute and Chronic Manifestations. The American Journal of Medicine. v. 50, p. 475-492, 1971. NATH, B.S & KUMAR, R.P.S. Toxic Impacto of Organophophorus Insecticides on Acetilcholinesterase Activity in the Silkworm, Bombyx mori L. Ecotoxicology and Environmental Safety. v. 42, p. 157-162. NOGUEIRA, A.J.M.; Dissertação de Mestrado, Universidade Federal Rural do Rio de Janeiro, 2007. 115 NUGENT, R.A.; SCHLACHTER, S.T.; MURPHY, M.; DUNN, C.J.; STAITE, N.D.; GALINET, L.A.; SHIELDS, S.K.; WU, H.; ASPAR, D.G.; RICHARD, K.A. Carbonyl- Containing Bisphosphonate Esters as Novel Antiinflamatory and Antiarthritic Agents. Journal of Medicinal Chemistry. v. 37, p. 4449-4454, 1994. NWAKA, S.; HUDSON, A. Innovative lead Discovery strategies for tropical diseases. Nat. Rev. Drug Discov. v.5, p. 941-955, 2006. O’BRIEN, R. D. Toxic phophorus esters. New York : Academica, p. 434, 1961. PADILHA, S.; WILSON, V. Z. & BUSHNELL, P. J. Toxicology. v. 92, p. 11-25, 1994. POPP, F. D. & PICCIRILLI, R. M. The Reaction of N-Acetylisatin with Amines. J. Heterocycl. Chem. v. 8. n. 6, p.473-475, 1971. POPP, F. D. Heterocycl. Chem. 18, 1, 1975. RAJSKI, R. S.; WILLIAMS, R. M. “DNA Cross-Linking Agents as Antitumor Drugs”. Chem. Rev. v. 98, p. 2733, 1998. RADUL, O. M.; ZHUNGIETU, G. I.; REKHTER, M. A.; BUKHANYUK, S. M. Simple Method for the Synthesis of 1-substituted isatins. Khim. Geterotsiki. Soedin. P. 353-5, 1983. RAMESH, A.; SRIDHAR, S.K.; PANDEYA, S.N.; STABLES, J.P. Anticonvulsant Activity of Hydrazones, Schiff and Manich Bases of Isatin Derivatives. European Journal of Pharmaceutical Sciences. v. 16, p. 129-132, 2002. RODRIGUES, J.M.; DaCOSTA, J.B.N. Synthesis and Characterization of New Symmetrical Bisphosphonates. Phosphorus Sulfur and Silicon and the Related Elements. v. 177, p. 137-149, 2002. RIBEIRO, T. S. Transformações químicas no alcalóide natural piperina e avaliação da atividade tóxica sobre Trypanosoma cruzi. Dissertação de Mestrado, UFRural, 2004. ROSATI, J. L. R.; DUTRA, A. A. M.; MORAES, A. C. L.; FERREIRA, M. C. L. &; ROCHA, L. F. R. Intoxicação por Carbamatos e Organofosforados. JBM. v. 69, n .3, p. 73- 96, 1995. SAADEH, A. M.; FARSAKH, N. A. & AL-ALI, M.K. Cardiac Manifestations of Acute Carbamate and Organophosphate Poisoning. Heart. v. 77, p. 461-464, 1997. SANDMEYER, T. Isonitrosoacetanilides and their condensation to from isatin derivatives. Helv. Chim. Acta. v. 2, p. 234, 1919. SELVAM, P.; CHANDRAMOHAN, M.; DE CLERCQ, E.; WITVROUW, M. E PANNECOUQUE, C. Synthesis and anti-HIV activity of 4-[(1,2-dihydro-2-oxo-3H-indol- 3-ylidene)amino]-N(4,6-dimethyl-2-pyrimidinyl)benzene sulfonamide and its derivatives. Eur. J. Pharm. Sci. v. 14, n. 4, p. 313, 2001. SILVA, J. F. M.; GARDEN, S. J. e PINTO, A. C. The chemistry of isatins: a review from 1975 to 1999. J. Braz. Chem. Soc. v. 12, n. 3, p. 273, 2001. SILVA, J. F. M. (1995) Síntese de benzoeterociclos a partir da isatina (1H-indol-2,3- diona). Monografia, IQ/UFRJ. SINDERMANN, H.; CROFT, S. L.; ENGEL, K. R.; BOMMER, W.; EIBL, H. J.; UNGER, C.; ENGEL, J. Miltefosine (Impavido): the first oral treatment against leishmaniasis. Med. Microbiol. Immunol. v. 193, p. 173-180, 2004. 116 SINGH, M. S.; MISHRA, G.; MEHROTRA, K. N. Novel and convenient one-pot synthesis of fused ring heterocycles from 1,2-diketones and phosphorodichloridate and phosphorothiodichloridate. Phosph. Sulf. Silicon. v. 63, n. 1/2, p. 177, 1991. SINGH, S.; BATRA,Y.K.; SINGH, S.M, WIG, N.; SHARMA, B.K. Is Atropine Alone Sufficient in Acute Severe Organophosphorous Poisoning.: Experience of a North West Indian Hospital. International Journal of clinical Pharmacology and Therapeutics. v. 33 n. 11, p. 628-630, 1995. SOARES, L.F. Intoxicações Agudas por Carbamatos em Pediatria. Aspectos Epidemiológicos, Clínicos e Terapêuticos. Rio de Janeiro. Monografia do Curso de Especialização em Pediatria da UFF, 1998. STOLLE, R. New method for the preparation of N-substituted isatins. Berichte Deut. Chem. Gesells. v. 46, p. 3915, 1914. SUMPTER, W.C & MILLER, F.M. Heterocyclic Compounds with Indole and Carbaloze Systems. The Chemistry of Heterocyclic Compounds. New York.1954. SZAJNMAN, S. H.; BAILEY, B. N.; DOCAMPO, R.; RODRIGUEZ, J. B.; Bioorg Med. Chem. Lett. v. 11, p. 789, 2001. TAYLOR, A. The synthesis of the dimethoxyisatins. J. Chem. Res. (S). v. 10, p. 347, 1980. TEICHER, B. A.; SOTOMAYOR, E. A. Em Cancer Chemotherapeutic Agents; Foye, W. O.; Americam Chemical Society: Washington, D.C.,1994. THOMAS, L.C. Interpretation of the Infrared Spectra of Organophosphorus Compounds. Heyden & Son, Ltd. London. 1974. THOMAS, L.C. The Identification of Functional Groups in Organophosphorus Compounds. Academic Press Inc. (London) LTD. 1st Ed., p. 79, 1974. TODD, A.R.; ATHERTON, F.R.; OPENSHAW, H.T. Journal of the Chemical Society. p.660, 1945. TODD, A.R.; ATHERTON, F.R. Journal of the Chemical Society. p.674, 1947. TODD, A.R.; ATHERTON, F.R.; HOWARD, H.T. Journal of the Chemical Society. p.1106, 1948. TOMCHIN, A. B & KRYLOVA, I. M. Semicarbazones and Thiosemicarbazones of the heterocyclic series. Reaction of 1-Acetilisatins with thiosemicarbazines. J. Org. Chem. USSR. v. 22, p. 2420-34. TOY, A.D.F., Phosphorus Chemistry in Everyday Living. Am. Chem. Soc. USA. 2nd Ed., p.154-155, 1977. TROUILLER, P.; OLLIARO, P.; TORREELE, E.; ORBINSKI, J.; LAING, R.; FORD, N. Drug development for neglected diseases: a deficient market and a public-health policy failure. The Lancet. p. 359, 2002. URBINA, J.A.; DOCAMPO, R. Specific chemotherapy of Chagas disease: controversies and advances. Trends in Parasitology. v.19, p. 495-501, 2003. VELEZ, I. D.; GILCHRIST, K.; ARBELAEZ, M. P.; ROJAS, C. A.; PUERTA, J.A.; ANTUNES, C.M.F.; ZICKER, F.; MODABBER, F. Failure of a killed Leishmania amazonensis vaccine againt American cutaneous leishmaniasis in Colombia. Trans. R. Soc. Trop. Med. Hyg. v. 99, p. 593-598, 2005. 117 WATIEN, F; DREJER, J; JENSEN, L.H. Preparation of isatin derivatives as central nervous system (CNS) agents. EP432648, p. 14, 1991. WEBBER, S. E.; TIKHE, J.; WORLAND, S. T.; FUHRMAN, S. A.; HENDRICKSON, T. F.; MATTHEWS, D. A.; LOVE, R. A.; PATICK, A. K.; MEADOR, J.W. Design, Synthesis, and Evaluation of Nonpeptidic Inhibitors of Human Rhinovirus 3C Protease. J. Med. Chem. v. 39, n. 26, p. 5072, 1996. WEI, L; WANG, Q; LIU, X. Application of thin-layer chromatography in quality control of Chinese medicinal preparations. II. Qualitative analysis of some Chinese medicinal preparations of Chansu. Yaowu Fenxi Zazhi. v. 2, p. 228-291, 1982. WHO/TDR – World Health Organization – Special Programme for Research and Training in Tropical Diseases, 2008. Disponível em <http://www.who.int/tdr/index.html>. Acessado em 16. Jan 2008. WHO, The World Health Report, 2000 & 2002 (World Health Organization, Geneva, 2002). WIDDUS, R. Public-private partnerships for health: their main targets, their diversity, and their future directions. Bull. World Health Organization. v. 79, p. 728-734, 2001. WORLD HEALTH ORGANIZATION. Control of Chagas disease: second report of the WHO expert committee. Geneva: WHO, 2002. (Technical Report Series, 905). YAMEY,G.; TORREELE, E. The worl’s most neglected diseases. BMJ. v. 325, p. 176 - 177, 2002. ZHAO, Y.F.; XI, S.K.; SONG, A.T.; JI, G.J. Phosphoryl as a Novel Amines Protecting Group for Friedel-Crafts Acylation of N-[2-(3,4-dialkoxy phenyl). Journal of Organic Chemistry. v. 49, p. 4549, 1984. ZHAO, Y.F.; XUE, C.B.; ZENG, J.N.; JI, G.J. Synthesis of N-(diisopropyloxyphosphoryl) Amino Acids and Peptides. Synthesis. v. 6, p. 444, 1988. YOCHIZAWA, M; MURAKAMI, T; KISHI, A; SAKURAMA, T; MATSUDA, H; NOMURA, M; MATSUDA, H; KUBO, M. Novel índole S,O-bisdesmoside, calanthoside, the precursor glycoside of tryptanthrin, indirubin, and isatin, with increasing skin blood flow promoting effects, from two Calanthe species (Orchidaceae). Chemical & Pharmaceutical Bulletin. v. 46, n. 5, p. 886-888, 1998.por
dc.rightsAcesso Abertopor
dc.subjectdialkylphosphorylhydrazoneseng
dc.subjectphosphorohydrazidic acideng
dc.subjectbiological activityeng
dc.subjectisatineng
dc.subjectDialquilfosforilidrazonaspor
dc.subjectácido fosforoidrazídicopor
dc.subjectatividade biológicapor
dc.subjectisatinapor
dc.subject.cnpqQuímicapor
dc.titleDialquilfosforilidrazonas derivadas de isatinas N - substituídas com potencial atividade biológicapor
dc.title.alternativeDialkylphosphorylhydrazones derived from N substituted isatins with potential biological activityeng
dc.typeDissertaçãopor
Appears in Collections:Mestrado em Química

Files in This Item:
File Description SizeFormat 
2009 - Leticia Silotti Zampirolli.pdf Leticia Silotti Zampirolli25.29 MBAdobe PDFThumbnail

Download/Open Preview
Show simple item record Recommend this item


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.