Antiplasmodial Activity of Naphthoquinones Related to Lapachol and<i>β</i>-Lapachone

Pérez-Sacau, Elisa; Estévez‐Braun, Ana; Ravelo, Ángel G.; Yapu, David Gutiérrez; Turba, Alberto Giménez

doi:10.1002/cbdv.200590009

Cited by 148 publications

(52 citation statements)

References 11 publications

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“…[1][2][3] Dentre as diversas metodologias para a obtenção dos derivados cíclicos, podemos citar aquelas que envolvem a ciclização direta do lapachol (1), de seu acetato 5 ou epóxido 6. [24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43] De modo geral, estas reações levaram à formação de uma mistura complexa de produtos. Entretanto, a α-xiloidona (2) pôde ser preparada em bons redimentos pelo refluxo de 1 em piridina, 24 pela sua transformação usando microorganismos, 25 ou pelo uso de MnO 2 como reagente.…”

Section: Introductionunclassified

“…Já a reação do lapachol (1) com PhSeCl levou à formação de 9 em 75% de rendimento, 34 enquanto a naftoquinona 10 foi isolada em 50% de rendimento na reação de 1 com N-bromosuccinimida (NBS) na presença de peróxido de benzoila, 35 mas em melhores rendimentos na reação do acetato do lapachol 5 com Br 2 (93% rendimento). 28 Derivados nitrogenados 11 foram obtidos em rendimentos moderados a partir da reação de 1 com aminas em condições básicas. 36 A reação de 1 com AMCPB (ácido meta-cloroperbenzóico) e ácido de Lewis, com ácido peracético ou H 2 O 2 levaram à formação de uma mistura complexa de derivados naftopirânicos e furânicos, 3,4,23,24,[38][39][40][41][42][43] incluindo a rinacantina-A (4) e os derivados 12-14, além de outros.…”

Section: Introductionunclassified

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Ciclização do lapachol induzida por sais de tálio III

Ribeiro¹,

Souza²,

Ferreira³

et al. 2008

Quím. Nova

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Recebido em 29/11/07; aceito em 7/3/08; publicado na web em 9/4/08 CYCLIZATION OF LAPACHOL INDUCED BY THALLIUM SALTS. This work describes the cyclization of lapachol (1) induced by thallium triacetate (TTA) and thallium trinitrate (TTN) in several solvents using magnetic stirring and under microwave irradiation. α-Xyloidone (2) -dehydro-α-lapachone -was obtained as the main product in these reactions in 20 -75% yield. However, rhinacanthin-A (4) was isolated as main product in a 40% yield, using TTA and acetic anhydride:water (1:1) as solvent, and dehydroiso-α-lapachone (3) in 21% yield, using TTA and dichloromethane as solvent. The reaction time decreased drastically under microwave conditions, but the yields of these reactions were not the expected.

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Section: Introductionunclassified

Ciclização do lapachol induzida por sais de tálio III

Ribeiro¹,

Souza²,

Ferreira³

et al. 2008

Quím. Nova

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“…[45][46][47][48][49][50][51][52] It also has a positive effect on wound-healing since low concentration of b-lapachone promoted the proliferation of keratinocytes, fibroblasts, and endothelial cells, as well as accelerated the migration of fibroblasts and EAhy926 cells through different mitogen-activated protein kinase (MAPK) signaling pathways. 53 In this study, it was used as a sample drug to investigate its effects on wound-healing and also to test the applicability of the ESWHC.…”

Section: Cell Preparationmentioning

confidence: 99%

In vitro electrical-stimulated wound-healing chip for studying electric field-assisted wound-healing process

2012

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The wound-healing assay is an easy and economical way to quantify cell migration under diverse stimuli. Traditional assays such as scratch assays and barrier assays are widely and commonly used, but neither of them can represent the complicated condition when a wound occurs. It has been suggested that wound-healing is related to electric fields, which were found to regulate wound re-epithelialization. As a wound occurs, the disruption of epithelial barrier shortcircuits the trans-epithelial potential and then a lateral endogenous electric field is created. This field has been proved in vitro as an important cue for guiding the migration of fibroblasts, macrophages, and keratinocytes, a phenomenon termed electrotaxis or galvanotaxis. In this paper, we report a microfluidic electricalstimulated wound-healing chip (ESWHC) integrating electric field with a modified barrier assay. This chip was used to study the migration of fibroblasts under different conditions such as serum, electric field, and wound-healingpromoting drugs. We successfully demonstrate the feasibility of ESWHC to effectively and quantitatively study cell migration during wound-healing process, and therefore this chip could be useful in drug discovery and drug safety tests.

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“…In addition, it can be obtained by the isomerization of lapachol, a quinone that is more abundant and more readily extracted from the same sources. The biological activities of these compounds and simple derivatives, have been investigated since the 1940's (anti-malarial 1 ) up to the present (anti-tumor, 2 anti-microbial, 3 anti-inflammatory 4 and anti-parasitic 5 ) and were recently reviewed. 6 The use of β-lapachone and some semi-synthetic derivatives as chemotherapic agents in the treatment of American trypanosomiasis (Chagas disease) has been investigated, 7 and five imidazole derivatives, prepared from this quinone and aromatic aldehydes, have shown expressive action over the tripamastigote form of Trypanosoma cruzi.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of imidazole derivatives from β-lapachone and related compounds using microwave and supported reagents

Silva¹,

Silva²,

Ferreira³

et al. 2008

J. Braz. Chem. Soc.

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Naftoimidazóis inéditos foram preparados por reação, ativada por microondas, entre paraformaldeído, β-lapachona (ou o-quinonas correlatas) e acetato de amônio suportado em montmorilonita k-10, ou em alumina básica. O uso do suporte básico forneceu os melhores rendimentos, superiores a 80%. Isso foi confirmado para a reação com β-lapachona e piperonal.New naphthoimidazoles were prepared by reaction, activated by microwave irradiation, between paraformaldehyde, β-lapachone (or related o-quinones) and ammonium acetate supported on montmorillonite k-10, or on basic alumina. Use of the basic support gave the best results, with yields above 80%. This was confirmed for the reaction with β-lapachone and piperonal.Keywords: imidazole, microwave, basic alumina, lapachone Introduction β-Lapachone (1a) is an ortho-naphthoquinone present in small amounts in trees of the Tabebuia species (Bignoniaceae), commonly called "ipê" or "pau d'arco" in Brazil. In addition, it can be obtained by the isomerization of lapachol, a quinone that is more abundant and more readily extracted from the same sources. The biological activities of these compounds and simple derivatives, have been investigated since the 1940's (anti-malarial 1 ) up to the present (anti-tumor, 2 anti-microbial, 3 anti-inflammatory 4 and anti-parasitic 5 ) and were recently reviewed. 6 The use of β-lapachone and some semi-synthetic derivatives as chemotherapic agents in the treatment of American trypanosomiasis (Chagas disease) has been investigated, 7 and five imidazole derivatives, prepared from this quinone and aromatic aldehydes, have shown expressive action over the tripamastigote form of Trypanosoma cruzi. 8,9 These imidazole derivatives were prepared by conventional methods. 9 As part of an ongoing study into the use of microwave activation and the use of supported reagents, in this case ammonium acetate, we investigated the preparation of the previously unknown simple imidazole derivatives of β-lapachone and related ortho-quinones with formaldehyde.Microwave activation has provided significant improvement on heterocyclic synthesis, 10 including imidazoles, with [11][12][13] or without support, 14,15 with reduction/ elimination of solvents, decreased reaction times and equal or improved yields. Results and DiscussionImidazole synthesis from α-diketones has a long history 16 and was initially plagued by low yields and by-products (such as oxazoles). Improvements occurred by the use of acidic conditions, e.g., glacial acetic acid reflux. 17 The availability of microwave technology for synthetic purposes has allowed the efficient preparation of 2,4,5-trissubstituted and 1,2,4,5-tetrassubstituted imidazoles. Further observed benefits, that were occasionally associated with solid supports such as silica, alumina, clays, amongst others, 11-13 included improved yields, and dramatic reductions in reaction time and quantities of solvent used (AcOH). 14,15 Interestingly, the best supports found in these studies were always the acidic in nature.Based on these findings, th...

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Antiplasmodial Activity of Naphthoquinones Related to Lapachol andβ-Lapachone

Cited by 148 publications

References 11 publications

Ciclização do lapachol induzida por sais de tálio III

Ciclização do lapachol induzida por sais de tálio III

In vitro electrical-stimulated wound-healing chip for studying electric field-assisted wound-healing process

Synthesis of imidazole derivatives from β-lapachone and related compounds using microwave and supported reagents

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