Síntese e determinação da atividade antimicrobiana de 2-[5-nitro-tiofen-2-il]-3-acetil-5-[4-fenil-substituído]-2,3-diidro-1,3,4-oxadiazol frente à cepa ATCC 25923 de Staphylococcus aureus

Almeida, Leonardo Viana de

doi:10.11606/d.9.2009.tde-07042010-131506

Cited by 2 publications

(5 citation statements)

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“…As células do inóculo foram cultivadas a 28 °C em meio LIT suplementado com 10% de soro (Cerecetto et al, 1999;Aguirre et al, 2002;Aguirre et al, 2004;Aguirre et al, 2005;Aran et al, 2005;Gerpe et al, 2010;Merlino et al, 2010;Jorge, 2010). (Masunari, 2005;Almeida, 2009;Jorge, 2010).…”

Section: Compostos Nitro-heterocíclicosunclassified

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Planejamento, síntese, determinação da atividade biológica e estudos de QSAR-2D de derivados 1,3,4-oxadiazolínicos frente ao Trypanosoma cruzi

Oliveira¹

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Section: Compostos Nitro-heterocíclicosunclassified

“…*Material de Partida: Base de Schiff. a:Almeida, 2009. Nota: o volume de anidrido acético utilizado foi de 10 mL (0,11 mol).…”

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Planejamento, síntese, determinação da atividade biológica e estudos de QSAR-2D de derivados 1,3,4-oxadiazolínicos frente ao Trypanosoma cruzi

Oliveira¹

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“…Para obtenção dos compostos furfurilidênicos azometínicos, 4a -j da série I, figura 16, ocorre a reação de condensação entre a benzidrazida, 3a -j, e o diacetato de 5-nitro-2-furfuraldeído com pureza de 98% (Sigma -Aldrich Chemical Company, Inc) (CAREY, SUNDBERG, 2000, SOLOMONS, FRYHLE, 2004, MARCH, 2001 , MACCIONI et al, 2011, ALMEIDA, 2009, LI, MA, CAO, 2009, SOMOGYI, 2007, ROLLAS, GULERMAN, ERDENIZ, 2002.…”

Section: Obtenção De Derivados Azometínicosunclassified

“…Para a análise de PCA, na matriz de dados, a atividade biológica foi considerada como variável dependente. Os dados foram decompostos em duas matrizes, uma de escores, relacionando as amostras, e outra de pesos (loadings), relacionando as variáveis (MONTANARI, 2011, BEEBE, PELL, SEASHOLTZ, 1998 , MACCIONI et al, 2011, ALMEIDA, 2009, LI, MA, CAO, 2009, SOMOGYI, 2007, JOULE, MILLS, 2007, ROLLAS, GULERMAN, ERDENIZ, 2002.…”

Section: Análise Exploratória Dos Dados: Hca E Pcaunclassified

“…As alíquotas do meio reacional para análise nas placas cromatográficas foram coletadas em diferentes momentos, sendo considerado o final da reação a formação de um Figura 30. Mecanismo de reação para obtenção de 2,3-di-idro-1,3,4-oxadiazolínico , ALMEIDA, L.V., 2009, JOULE, MILLS, 2007 FBT (TYLER, ENGMAN, 2001, ALMEIDA-DE-FARIA et al1999, FAUCHER, BALTZ, PETRY, 1995 , GERPE et al, 2010,CERECETTO et al, 1998.…”

Section: Análise Exploratória Dos Dados: Hca E Pcaunclassified

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Planejamento, síntese e avaliação da atividade anti-T. cruzi de derivados furfurilidênicos com estruturas azometínica e oxadiazolínica

Palace-Berl¹

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The search for alternative therapies for the treatment of Chagas disease presents great importance, since there are only two currently available drugs, nifurtimox and benznidazole. Both have considerable adverse effects and, in Brazil, is used only benznidazole. Nitro-heterocyclic compounds with activity against Trypanosoma cruzi, the causative agent of Chagas disease, has shown promising results. Thus, this work includes the design, synthesis, identification, evaluation of anti-T. cruzi activity of 5-nitro-2furfuriliden (IC 50 T. cruzi) and cytotoxicity of these compounds against J774 macrophages cell line (IC 50 J774). The nifuroxazide, as a lead compound, inspired the molecular modification leading to two series of furfuriliden compounds, a azometinic structure, series I, and other with oxadiazolinic structure, series II. The choice of substituents was based on the Craig's diagram, and ten substituents were selected for each series. We evaluated the activity of twenty compounds designed against T. cruzi, and the most active compounds were: 4-butyl-[N'-(5-nitrofuran-2-yl) methylene] benzidrazide (4g-IC 50 T. cruzi = 1.05 μM, SD = 0.07) and 3-acetyl-5-(4-butylphenyl)-2-(5-nitrofuran-2-yl)-2,3-dihydro, 1,3,4-oxadiazole (5g-IC 50 T. cruzi = 8.27 μM, SD = 0.42). Compared to the reference drugs, benznidazole (IC 50 T. cruzi = 22.69 μM, SD = 1.96) and nifurtimox (IC 50 T. cruzi = 3.78 μM, SD = 0.10), the compound 4g demonstrated anti-T. cruzi activity superior to both drugs. All compounds showed better activity than nifuroxazide (IC 50 T. cruzi = 120.46 μM, SD = 4.06). For cytotoxicity assays, was found for the most active compound against T. cruzi, 4g, IC 50 J774 = 28.05 μM, SD = 1.05, and for compound 5g was obtained IC 50 J774 = >400 μM, that represents the maximum concentration of the compound evaluated which did not affect the cells. Both showed good selectivity in the calculation of the ratio between the IC 50 T. cruzi and IC 50 J774. Additionally, we performed calculations of the physicochemical properties of three-dimensional structures of the compounds, followed by exploratory data analysis including hierarchical cluster analysis (HCA) and principal component analysis (PCA), which contributed to the identification of properties that influence the activity anti-T. cruzi in the series of compounds studied. The findings indicated a significant influence of ClogP and dipole moment properties, pointing out the need of a lipophilic/hydrophilic balance in the designing of novel anti-T.

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Síntese e determinação da atividade antimicrobiana de 2-[5-nitro-tiofen-2-il]-3-acetil-5-[4-fenil-substituído]-2,3-diidro-1,3,4-oxadiazol frente à cepa ATCC 25923 de Staphylococcus aureus

Cited by 2 publications

References 26 publications

Planejamento, síntese, determinação da atividade biológica e estudos de QSAR-2D de derivados 1,3,4-oxadiazolínicos frente ao Trypanosoma cruzi

Planejamento, síntese, determinação da atividade biológica e estudos de QSAR-2D de derivados 1,3,4-oxadiazolínicos frente ao Trypanosoma cruzi

Planejamento, síntese e avaliação da atividade anti-T. cruzi de derivados furfurilidênicos com estruturas azometínica e oxadiazolínica

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