S?ntese N-benzil e N-fenetil-amidas na aus?ncia de solvente e Avalia??o da atividade antichagasi de fenil-tiossemicarbazonas fluoro-substitu?das
| Ano de defesa: | 2015 |
|---|---|
| Autor(a) principal: |
Santos, Jonas da Silva
 |
| Orientador(a): |
Lima, Aurea Echevarria Aznar Neves
|
| Banca de defesa: |
Lima, Aurea Echevarria Aznar Neves
,
Santos, Cl?udio Eduardo Rodrigues dos
,
Mello, Heloisa de
,
Suzart, Luciano Ramos
|
| Tipo de documento: | Dissertação |
| Tipo de acesso: | Acesso aberto |
| Idioma: | por |
| Instituição de defesa: |
Universidade Federal Rural do Rio de Janeiro
|
| Programa de Pós-Graduação: |
Programa de P?s-Gradua??o em Qu?mica
|
| Departamento: |
Instituto de Ci?ncias Exatas
|
| País: |
Brasil
|
| Palavras-chave em Português: | |
| Palavras-chave em Inglês: | |
| Área do conhecimento CNPq: | |
| Link de acesso: | https://tede.ufrrj.br/jspui/handle/jspui/5403 |
Resumo: | Neglected tropical diseases (NTDs) are a group of endemic diseases caused by infectious and parasitic agents; they thrive mainly among the poorest populations due to the lack of sanitation. Results found by our research group in previous studies indicated the importance of amides against Leishmania parasites. Recently, studies of a series of thiosemicarbazones have shown promising results against Leishmania amazonensis and Trypasnosoma cruzi. In this work, 21 amides were synthesised through two different synthetic methodologies (A & B), using comparative intention-to-treat analysis with green chemistry, aiming at assays against parasites from the trypanosomatid class. Comparative studies of these synthesis indicate the most efficient way was activated by grinding (reaction in the absence of solvent, methodology B). When the methodologies were compared, it was observed that: atom economy (AE%) was higher than 60% in methodology B, about 27% higher than in methodology A; reaction mass efficiency (RME) was also more significant in methodology B; and, the e-factor involved in the obtaining of amides was lower in methodology B. In addition, a series of 10 fluorided thiosemicarbazones were assayed against T. cruzi, and QSAR studies involving physicochemical descriptors were performed. Assays were done in microplates of 96 wells at the following concentrations: 100.0; 50.0; 25.0; 12.5; 6.25; 3.125 mg/mL, diluted in dimethyl-sulfoxide solution (DMSO) in LIT medium. IC50 values varied between 5.64 and 29.19 ?g.mL-1. After the structural theoretical parameters, experimental data and biological activity had been compared in QSAR studies, 5 significant mathematical models were found presenting lipophilicity, electronic effects and pKa as the most important factors for the anti-Chagas activity |
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Lima, Aurea Echevarria Aznar Neves668.742.388-68http://lattes.cnpq.br/1879077396134052Santos, Cl?udio Eduardo Rodrigues dos078.357.167-47https://orcid.org/0000-0003-0129-2802http://lattes.cnpq.br/0890271430013129Lima, Aurea Echevarria Aznar Neves668.742.388-68http://lattes.cnpq.br/1879077396134052Santos, Cl?udio Eduardo Rodrigues dos078.357.167-47https://orcid.org/0000-0003-0129-2802http://lattes.cnpq.br/0890271430013129Mello, Heloisa dehttp://lattes.cnpq.br/2981920434610982Suzart, Luciano Ramoshttp://lattes.cnpq.br/9433715032329261030.937.925-33http://lattes.cnpq.br/4498497181229068Santos, Jonas da Silva2022-02-18T11:49:39Z2015-08-31SANTOS, Jonas da Silva. S?ntese N-benzil e N-fenetil-amidas na aus?ncia de solvente e Avalia??o da atividade antichagasi de fenil-tiossemicarbazonas fluoro-substitu?das. 2015. 209 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica, RJ, 2015https://tede.ufrrj.br/jspui/handle/jspui/5403Neglected tropical diseases (NTDs) are a group of endemic diseases caused by infectious and parasitic agents; they thrive mainly among the poorest populations due to the lack of sanitation. Results found by our research group in previous studies indicated the importance of amides against Leishmania parasites. Recently, studies of a series of thiosemicarbazones have shown promising results against Leishmania amazonensis and Trypasnosoma cruzi. In this work, 21 amides were synthesised through two different synthetic methodologies (A & B), using comparative intention-to-treat analysis with green chemistry, aiming at assays against parasites from the trypanosomatid class. Comparative studies of these synthesis indicate the most efficient way was activated by grinding (reaction in the absence of solvent, methodology B). When the methodologies were compared, it was observed that: atom economy (AE%) was higher than 60% in methodology B, about 27% higher than in methodology A; reaction mass efficiency (RME) was also more significant in methodology B; and, the e-factor involved in the obtaining of amides was lower in methodology B. In addition, a series of 10 fluorided thiosemicarbazones were assayed against T. cruzi, and QSAR studies involving physicochemical descriptors were performed. Assays were done in microplates of 96 wells at the following concentrations: 100.0; 50.0; 25.0; 12.5; 6.25; 3.125 mg/mL, diluted in dimethyl-sulfoxide solution (DMSO) in LIT medium. IC50 values varied between 5.64 and 29.19 ?g.mL-1. After the structural theoretical parameters, experimental data and biological activity had been compared in QSAR studies, 5 significant mathematical models were found presenting lipophilicity, electronic effects and pKa as the most important factors for the anti-Chagas activityAs doen?as classificadas como negligenciadas s?o constitu?das por um grupo de endemias causadas por agentes infecciosos e parasit?rios, atacando principalmente popula??es de baixa renda que sofrem por falta de saneamento b?sico. Resultados de trabalhos anteriores de nosso grupo de pesquisa indicaram a import?ncia de amidas frente a parasitas do g?nero Leishmania. Recentemente, estudos frente ? Leishmaniaamazonensis e Trypasnosoma cruzi mostraram-se extremamente promissores para uma s?rie de tiossemicarbazonas. Neste trabalho foram sintetizadas 21 amidas por duas vias sint?ticas distintas (metodologia A e metodologia B) com intuito comparativo, baseando-se nos princ?pios da Qu?mica Verde, visando os ensaios frente a parasitos da classe dos tripanossomat?deos. O estudo comparativo destas s?nteses aponta para uma via mais eficaz, ativada por ?grinding? (rea??o na aus?ncia de solvente, metodologia B). Quando correlacionando as metodologias A e B, observou-se que: foram obtidos valores maiores que 60% de economia at?mica (EA%) na metodologia B, cerca de 27% a mais que a metodologia A; a efici?ncia de massa da rea??o (EMR) tamb?m apresenta valores mais expressivos na metodologia B; e o fator-e envolvido na obten??o destas amidas ? menor na metodologia B. Foram realizados ainda, ensaios frente a T. cruzi por uma s?rie de 10 tiossemicarbazonas fluoradas, bem como o estudo de QSAR envolvendo descritores f?sico-qu?micos te?ricos. Os ensaios foram realizados em microplacas de 96 po?os na concentra??o de 100,0; 50,0; 25,0; 12,5; 6,25; 3,125 mg/mL dilu?das em solu??o de dimetil-suf?xido (DMSO) em meio LIT. O valor de IC50 variou de 5,64 - 29,19 ?g.mL-1 . Ap?s o estudo de QSAR, correlacionando par?metros te?ricos estruturais, dados experimentais e atividade biol?gica, chegou-se a 5 modelos matem?ticos significativos, que apresentam como fatores de maior import?ncia a lipofilicidade, os efeitos eletr?nicos e pKa para a atividade antichagasiSubmitted by Celso Magalhaes (celsomagalhaes@ufrrj.br) on 2022-02-18T11:49:39Z No. of bitstreams: 1 2015 - Jonas da Silva Santos.pdf: 3600031 bytes, checksum: 14572a0a99caaedd0eba6e60027dd447 (MD5)Made available in DSpace on 2022-02-18T11:49:39Z (GMT). No. of bitstreams: 1 2015 - Jonas da Silva Santos.pdf: 3600031 bytes, checksum: 14572a0a99caaedd0eba6e60027dd447 (MD5) Previous issue date: 2015-08-31CAPES - Coordena??o de Aperfei?oamento de Pessoal de N?vel Superiorapplication/pdfhttps://tede.ufrrj.br/retrieve/68253/2015%20-%20Jonas%20da%20Silva%20Santos.pdf.jpgporUniversidade Federal Rural do Rio de JaneiroPrograma de P?s-Gradua??o em Qu?micaUFRRJBrasilInstituto de Ci?ncias ExatasABAD, A.; AGUIL?, C.; CU?AT, A. C.; VILANOVA, C.; 1H, 13C and 19F NMR spectroscopy of polyfluorinated ureas. Correlations involving NMR chemical shifts and electronic substituent effects. Magn. Reson. Chem.2005; 43: 389-397. AKAMANCHI, K. G.; CHAUDHARI, P. S.; SALIM, S. D.; SAWANT, R. V.; Sulfated tungstate: a new solid heterogeneous catalyst for amide synthesis. The Royal Society of Chemistry - Green Chem., 2010, 12, 1707?1710 ALBUQUERQUE, M. A.; GOULART, C. M.; AMORIM, A. P. O.; OLIVEIRA, M. C. 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H.; RICHER, J.-C., Guia IUPAC para a Nomenclatura de Compostos Org?nicos, tradu??o portuguesa nas variantes Europ?ia e Brasileira de A Guide to IUPAC Nomeclature or Organic Compounds Recomendations 1993?: Lidel edi??es t?cnicas lta; Lisboa, 2002 PARASITOLOGY IMAGES: AN AUTO-TUTORIAL WITH ADDITIONAL INSTRUCTIONAL AIDS. Life Cycles. Life Cycle of Leishmania spp. Dispon?vel em: <http://158.83.1.40/Buckelew/Leishmania%20life%20cycle.htm>. Acesso em 07 fev. 2014. 96 PARDIN, C.; LUBELL, W. D.; PELLETIER, J. N.; KEILLOR, J. W.; Cinnamoyl inhibitors of tissue transglutaminase. Journal of Organic Chemistry, 2008, V73(15), 5766-5775. PARK, K.; LEE, B.M.; KIM, Y.H.; HAN, T.; YI, W.; LEE, D.H.; CHOI, H.H.; CHONG, W.; LEE, C.H.; Discovery of a novel phenylethyl benzamide glucokinase activator for the treatment of type 2 diabetes mellitus. Bioorganic & Medical Chemistry Letters. Vol. 23, (2013) 537-542. PEREIRA, I.O.; MARQUES, M.J.; PAVAN, A.L.R.; CODONHO, B.S.; BARBIERI, C.L.; BEIJO, L.A.; DORIGUETTO, A.C.; D?MARTIN, E.C.; SANTOS, M.H.; Leishmanicidal activity of benzophenones and extracts from Garcinia brasiliensis Mart. Fruits. Phytomedicine: International Journal of Phytotherapy & Phytopharmacology, doi:10.1016/j.phymed.2009.07.020., 1 abril 2010. PEYSSELON, F., LAUNAY, G., LISACEK, F., DUCLOS, B., RICARD-BLUM, S.; Comparative analysis of Leishmania exoproteomes: Implication for host?pathogen interactions; Biochimica et Biophysica Acta, 1834, 2653?2662, 2013. POLANSKI, J.; SERAFINA, K.; MAZUR, P.; BAK, A.; LAINE, E.; TCHERTANOV, L.; MOUSCADET, J.F.; Ethyl malonate amides: A diketo acid offspring fragment for HIV integrase inhibition. Bioorganic & Medicinal Chemistry 19 (2011) 5000?5005 POLSHETTIWAR, V.; VARMA, R. S.; Nafion?-catalyzed microwave-assisted Ritter reaction: an atom-economic solvent-free synthesis of amides. Tetrahedron Letters 49 (2008) 2661?2664. 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Rio de Janeiro: LTC, 2010. SMEE, D.F., SIDWELL, R.W., 2003. A review of compounds exhibiting ant orthopoxvirus activity in animal models. Antiviral Research 57, 41?52. SMITH, M. B., MARCH, J.; March?s Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, Sixth Edition, 2007. SOARES, R.O.A.; ECHEVARRIA, A.; BELLIENY, M.S.S.; PINHO, R.T.; LEO, R.M.M.; SEGUINS, W.S.; MACHADO, G.M.; CANTO-CAVALHEIRO, M.M.; LEON, L. L.; Evaluation of thiosemicarbazones and semicarbazones as potential agents anti-Trypanosoma cruzi. Experimental Parasitology 129 (2011) 381?387 98 SOLOMONS, T.W.G.; FRYHLE, C.B. Qu?mica Org?nica. Rio de Janeiro: LTC Editora. Vol 1, 9a ed., 2009. SOUZA, W. Doen?as negligenciadas / Wanderley de Souza, coordenador. ? Rio de Janeiro: Academia Brasileira de Ci?ncias, 2010. 56 p. :il. ? (Ci?ncia e tecnologia para o desenvolvimento nacional. Estudos estrat?gicos). STOTHERS, J. B.; Carbon-13 NMR Spectroscopy. Organic Chemistry, V 24, Academic Press, INC. (LONDON) LTD, 1972. DAS, V. K.; DEVI, R. R.; THAKUR, A. J.; Recyclable, highly efficient and low cost nano-MgO for amide synthesis under SFRC: A convenient and greener ?NOSE? approach. Applied Catalysis A: General 456 (2013) 118?125. TAVARES, L. C.; QSAR: a abordagem de Hansch. Quim. Nova, Vol. 27, No. 4, 631- 639, 2004. TEN?RIO, R. P.; G?ES, A. J. S.; LIMA, J. G.; FARIA, A. R.; ALVES, A. J.; AQUINO, T. M.; Tiossemicarbazonas: M?todos De Obten??o, Aplica??es Sint?ticas E Import?ncia Biol?gica. Quim. Nova, Vol. 28, No. 6, 1030-1037, 2005. TOGO, H.; KAWAGOE, Y.; MORIYAOMA, K.; Facile preparation of amides from carboxylic acids anda mines with ion-supported PH3P. Tetrahedrom, 69, 3971-3977, 2013. TORRES-SANTOS, E.C., LOPES, D., OLIVEIRA, R.R., CARAUTA, J.P.P., FALCAO, C.C.B., KAPLAN, M.A.C., ROSSI-BERGMANN, B., Antileishmanial activity of isolated triterpenoids from Pourouna guianensis. Phytomedicine 11: 114- 120, 2004. TUNDO, P. et al. Synthetic pathaways and processes in green chemistry. Introductory overview. 7. ed. [S.l.]: IUPAC, Pure and Applied Chemistry, v. 72, 2000. VALVERDE, R.. Doen?as negligenciadas. Agencia FioCruz de Noticias. Dispon?vel em: http://www.agencia.fiocruz.br/doen%C3%A7as-negligenciadas. Acesso em 16 de dezembro de 2014. 99 VENDRAMETTO, M. C., SANTOS, A. O., NAKAMURA, C. V., FILHO, B. P. D., CORTEZ, D. A. G., UEDA-NAKAMURA, T.; Evaluation of antileishmanial activity of eupomatenoid-5, a compound isolated from leaves of Piper regnelliivar.pallescens; Parasitology International, 59, 154?158, 2010. WHO/TDR - Tropical Diseases Research ? Leishmaniasis Fourteen Programme Report: 101-111, 1997. ZHANG, M.; WU, X-F.; Zinc(II)-catalyzed oxidative amidation of arylaldehydes with alkylamines under solvent-free conditions. 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| dc.title.por.fl_str_mv |
S?ntese N-benzil e N-fenetil-amidas na aus?ncia de solvente e Avalia??o da atividade antichagasi de fenil-tiossemicarbazonas fluoro-substitu?das |
| dc.title.alternative.por.fl_str_mv |
Synthesis of N-benzyl and phenethyl-amides in solvent-free and evaluation of the antichagasi activity of fluoro-substituted phenyl-thiosemicarbazones |
| title |
S?ntese N-benzil e N-fenetil-amidas na aus?ncia de solvente e Avalia??o da atividade antichagasi de fenil-tiossemicarbazonas fluoro-substitu?das |
| spellingShingle |
S?ntese N-benzil e N-fenetil-amidas na aus?ncia de solvente e Avalia??o da atividade antichagasi de fenil-tiossemicarbazonas fluoro-substitu?das Santos, Jonas da Silva Amidas Qu?mica verde Tiossemicarbazonas Atividade antichagas QSAR Amides Green chemistry Thiosemicarbazones Anti-Chagas activity QSAR Qu?mica |
| title_short |
S?ntese N-benzil e N-fenetil-amidas na aus?ncia de solvente e Avalia??o da atividade antichagasi de fenil-tiossemicarbazonas fluoro-substitu?das |
| title_full |
S?ntese N-benzil e N-fenetil-amidas na aus?ncia de solvente e Avalia??o da atividade antichagasi de fenil-tiossemicarbazonas fluoro-substitu?das |
| title_fullStr |
S?ntese N-benzil e N-fenetil-amidas na aus?ncia de solvente e Avalia??o da atividade antichagasi de fenil-tiossemicarbazonas fluoro-substitu?das |
| title_full_unstemmed |
S?ntese N-benzil e N-fenetil-amidas na aus?ncia de solvente e Avalia??o da atividade antichagasi de fenil-tiossemicarbazonas fluoro-substitu?das |
| title_sort |
S?ntese N-benzil e N-fenetil-amidas na aus?ncia de solvente e Avalia??o da atividade antichagasi de fenil-tiossemicarbazonas fluoro-substitu?das |
| author |
Santos, Jonas da Silva |
| author_facet |
Santos, Jonas da Silva |
| author_role |
author |
| dc.contributor.advisor1.fl_str_mv |
Lima, Aurea Echevarria Aznar Neves |
| dc.contributor.advisor1ID.fl_str_mv |
668.742.388-68 |
| dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/1879077396134052 |
| dc.contributor.advisor-co1.fl_str_mv |
Santos, Cl?udio Eduardo Rodrigues dos |
| dc.contributor.advisor-co1ID.fl_str_mv |
078.357.167-47 https://orcid.org/0000-0003-0129-2802 |
| dc.contributor.advisor-co1Lattes.fl_str_mv |
http://lattes.cnpq.br/0890271430013129 |
| dc.contributor.referee1.fl_str_mv |
Lima, Aurea Echevarria Aznar Neves |
| dc.contributor.referee1ID.fl_str_mv |
668.742.388-68 |
| dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/1879077396134052 |
| dc.contributor.referee2.fl_str_mv |
Santos, Cl?udio Eduardo Rodrigues dos |
| dc.contributor.referee2ID.fl_str_mv |
078.357.167-47 https://orcid.org/0000-0003-0129-2802 |
| dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/0890271430013129 |
| dc.contributor.referee3.fl_str_mv |
Mello, Heloisa de |
| dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/2981920434610982 |
| dc.contributor.referee4.fl_str_mv |
Suzart, Luciano Ramos |
| dc.contributor.referee4Lattes.fl_str_mv |
http://lattes.cnpq.br/9433715032329261 |
| dc.contributor.authorID.fl_str_mv |
030.937.925-33 |
| dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/4498497181229068 |
| dc.contributor.author.fl_str_mv |
Santos, Jonas da Silva |
| contributor_str_mv |
Lima, Aurea Echevarria Aznar Neves Santos, Cl?udio Eduardo Rodrigues dos Lima, Aurea Echevarria Aznar Neves Santos, Cl?udio Eduardo Rodrigues dos Mello, Heloisa de Suzart, Luciano Ramos |
| dc.subject.por.fl_str_mv |
Amidas Qu?mica verde Tiossemicarbazonas Atividade antichagas QSAR |
| topic |
Amidas Qu?mica verde Tiossemicarbazonas Atividade antichagas QSAR Amides Green chemistry Thiosemicarbazones Anti-Chagas activity QSAR Qu?mica |
| dc.subject.eng.fl_str_mv |
Amides Green chemistry Thiosemicarbazones Anti-Chagas activity QSAR |
| dc.subject.cnpq.fl_str_mv |
Qu?mica |
| description |
Neglected tropical diseases (NTDs) are a group of endemic diseases caused by infectious and parasitic agents; they thrive mainly among the poorest populations due to the lack of sanitation. Results found by our research group in previous studies indicated the importance of amides against Leishmania parasites. Recently, studies of a series of thiosemicarbazones have shown promising results against Leishmania amazonensis and Trypasnosoma cruzi. In this work, 21 amides were synthesised through two different synthetic methodologies (A & B), using comparative intention-to-treat analysis with green chemistry, aiming at assays against parasites from the trypanosomatid class. Comparative studies of these synthesis indicate the most efficient way was activated by grinding (reaction in the absence of solvent, methodology B). When the methodologies were compared, it was observed that: atom economy (AE%) was higher than 60% in methodology B, about 27% higher than in methodology A; reaction mass efficiency (RME) was also more significant in methodology B; and, the e-factor involved in the obtaining of amides was lower in methodology B. In addition, a series of 10 fluorided thiosemicarbazones were assayed against T. cruzi, and QSAR studies involving physicochemical descriptors were performed. Assays were done in microplates of 96 wells at the following concentrations: 100.0; 50.0; 25.0; 12.5; 6.25; 3.125 mg/mL, diluted in dimethyl-sulfoxide solution (DMSO) in LIT medium. IC50 values varied between 5.64 and 29.19 ?g.mL-1. After the structural theoretical parameters, experimental data and biological activity had been compared in QSAR studies, 5 significant mathematical models were found presenting lipophilicity, electronic effects and pKa as the most important factors for the anti-Chagas activity |
| publishDate |
2015 |
| dc.date.issued.fl_str_mv |
2015-08-31 |
| dc.date.accessioned.fl_str_mv |
2022-02-18T11:49:39Z |
| dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
| dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
| format |
masterThesis |
| status_str |
publishedVersion |
| dc.identifier.citation.fl_str_mv |
SANTOS, Jonas da Silva. S?ntese N-benzil e N-fenetil-amidas na aus?ncia de solvente e Avalia??o da atividade antichagasi de fenil-tiossemicarbazonas fluoro-substitu?das. 2015. 209 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica, RJ, 2015 |
| dc.identifier.uri.fl_str_mv |
https://tede.ufrrj.br/jspui/handle/jspui/5403 |
| identifier_str_mv |
SANTOS, Jonas da Silva. S?ntese N-benzil e N-fenetil-amidas na aus?ncia de solvente e Avalia??o da atividade antichagasi de fenil-tiossemicarbazonas fluoro-substitu?das. 2015. 209 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica, RJ, 2015 |
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https://tede.ufrrj.br/jspui/handle/jspui/5403 |
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por |
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openAccess |
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UFRRJ |
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