2006
DOI: 10.1590/s0074-02762006000200009
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Abstract: The natural lignans veraguensin and grandisin have been reported to be active against Trypanosoma cruzi bloodstream forms. Aiming at the total synthesis of these and related compounds, we prepared three 2-arylfurans and eight 2,5-diarylfurans. They were evaluated for their potential as T. cruzi trypanothione reductase (TR) 60% at 20 µg/ml (59 and 90 µM, respectively). On the other hand, none of the compounds was significantly active against the parasite bloodstream forms even at 250 µg/ml (0.6-1.5 mM).Key… Show more

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Cited by 37 publications
(25 citation statements)
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“…Recentemente demonstramos que o 2,5-bis-(4-acetilaminofenil)furano (1) é capaz de inibir, na concentração de 48 μM, 50% da atividade da TR 9 . Apesar de apresentar uma atividade considerável como inibidor da TR, a diacetamida (1) não foi ativa nos ensaios in vitro utilizando as formas tripomastigota e amastigota do T. cruzi.…”
Section: Introductionunclassified
See 1 more Smart Citation
“…Recentemente demonstramos que o 2,5-bis-(4-acetilaminofenil)furano (1) é capaz de inibir, na concentração de 48 μM, 50% da atividade da TR 9 . Apesar de apresentar uma atividade considerável como inibidor da TR, a diacetamida (1) não foi ativa nos ensaios in vitro utilizando as formas tripomastigota e amastigota do T. cruzi.…”
Section: Introductionunclassified
“…Apesar de apresentar uma atividade considerável como inibidor da TR, a diacetamida (1) não foi ativa nos ensaios in vitro utilizando as formas tripomastigota e amastigota do T. cruzi. Uma explicação para este fato pode estar relacionada com a baixa solubilidade de (1) (LogP = 0,39, calculado usando o programa HyperChem 6.02), o que dificulta sua penetração no parasita e, conseqüentemente, a impede de alcançar concentrações suficientes para a inibição persistente da TR 9 . Visando a obtenção de inibidores mais ativos e que apresentem melhores características físico-químicas, uma série de aminas e amidas análogas a (1) foi planejada e sintetizada.…”
Section: Introductionunclassified
“…These compounds have been considered important scaffolds in molecular modification studies due to their antileishmanial and antichagasic activities [13][14][15][16]. Cassamale et al [12] demonstrated the antileishmanial activity of these triazole derivatives on promastigote forms; now the present work shows their activity on L. (L.) amazonensis intracellular amastigotes, searching for structure-activity relationship information to support the development of new drug candidates for CL.…”
Section: Introductionmentioning
confidence: 57%
“…The residue purified by column chromatography on silica gel using hexane/ethyl acetate 8:2 as eluent. General procedure for the preparation of triazole derivatives (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) To a solution of terminal acetylenes 25a-d (2 mmol, 1.0 equiv) and azides 27a-d (2 mmol, 1.0 equiv) in dichloromethane (2 mL) and water (2 mL), were added CuSO 4 .5H 2 O pentahydrate (0.128 mmol, 0.064 equiv) and sodium ascorbate (0.352 mmol, 0.176 equiv). The reaction mixture was stirred for 24 h. Then was added a saturated solution of NH 4 Cl (30 mL) and the product was extracted with dichloromethane (3 × 20 mL).…”
Section: General Remarksmentioning
confidence: 99%
“…10,12,13 Among natural products, our research group has focused on the tetrahydrofuran neolignans, a class that exhibits a great number of biological activities including antibacterial, antifungal, antitumor, and anti-inflammatory. [14][15][16][17][18][19][20][21][22][23] The neolignans veraguensin 1, grandisin 2, and machilin G 3 ( Figure 1) have shown antitrypanosomal and antileishmanial activities. [14][15][16][17][18][19][20][21][22][23] Studies on the antitrypanosomal activity of compounds 1-3 found maximum inhibitory concentration (IC 50 ) values of 2.3, 3.7 and 2.2 µM, respectively.…”
Section: Introductionmentioning
confidence: 99%