Synthesis of chalcone analogues with increased antileishmanial activity

Boeck, Paula; Falcão, Camila Alves Bandeira; Leal, Paulo César; Yunes, Rosendo A.; Filho, Valdir Cechinel; Torres-Santos, Eduardo Caio; Rossi-Bergmann, Bartira

doi:10.1016/j.bmc.2005.10.005

Cited by 230 publications

(157 citation statements)

References 17 publications

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“…Já foi relatada a atividade leishmanicida de terpenóides Camacho et al, 2000), aminoglicosteróides e aminosteróides (Kam et al, 1997), naftoquinonas (Fournet et al, 1992;Kayser et al, 2000), chalconas (Chen et al, 1993;Boeck et al, 2006), glicosídios iridóides (Mittal et al, 1998), fl avonóides (Araújo et al, 1998), lignanas (Barata et al, 2000;Royo et al, 2003) e de alcalóides (Mahiou et al, 1994;Fournet et al, 1996;Queiroz, et al, 1996). Apesar dos vários estudos nesta área, ainda existem muitas espécies vegetais com potencial atividade leishmanicida a serem avaliadas.…”

Section: Resultsunclassified

Avaliação da atividade leishmanicida in vitro de plantas medicinais

Bezerra¹,

Costa²,

Lopes³

et al. 2006

Rev. bras. farmacogn.

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31.3, 62.5, 125.0, 250.0 and 500.0 μg/mL of each extract. Then the inhibitory concentration of the parasite growth (IC 50 ) was determined. The effectiveness of J. triqueter, Dichorisandra sp and T. cinerea hydroalcoholic extracts to induce promastigotes death was intense since the IC 50 were 29.5; 32.9 and 43.6 μg/mL, respectively. P. edulis, C. ambrosioides and S. jambolanum extracts had moderated effectiveness since the IC 50 were 150.1; 151.9 and 166.6 μg/mL, respectively. P. tithymaloides and O. phalerata extracts showed a low effi cacy in comparison with IC 50 >500 μg/mL. Peristrophe angustifolia and Cecropia sp extracts had no leishmanicidal effect. Thus, three of the ten extracts that were tested showed a signifi cant in vitro leishmanicidal activity.

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Section: Resultsunclassified

Avaliação da atividade leishmanicida in vitro de plantas medicinais

Bezerra¹,

Costa²,

Lopes³

et al. 2006

Rev. bras. farmacogn.

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“…A previous study showed that triclosan and quinoline-triclosan hybrids with shorter spacers, that is three and five methylene units, have in vitro activity against axenic and intracellular amastigotes with effective concentration (EC 50 ) below of 24 µg/mL) of Leishmania panamensis [9]. Similarly, antileishmanial activity of several chalcones has been reported [10][11][12]. The most promising of this class of compounds is licochalcone A, an oxygenated chalcone isolated from the roots of the Chinese plant Glycyrrhiza spp., which inhibits the fumarate reductase, a selective target present in the mitochondria of the parasite [13].…”

Section: Introductionmentioning

confidence: 94%

Synthesis, Leishmanicidal and Cytotoxic Activity of Triclosan-Chalcone, Triclosan-Chromone and Triclosan-Coumarin Hybrids

et al. 2014

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Twelve hybrids derived from triclosan were obtained via Williamson etherification of O-triclosan alkyl bromide plus chalcone and O-coumarin or O-chromone alkyl bromide plus triclosan, respectively. Structures of the products were elucidated by spectroscopic analysis. The synthesized compounds were evaluated for antileishmanial activity against L. (V) panamensis amastigotes. Cytotoxic activity was also evaluated against mammalian U-937 cells. Compounds 7-9 and 17, were active against Leishmania parasites (EC 50 = 9.4; 10.2; 13.5 and 27.5 µg/mL, respectively) and showed no toxicity toward mammalian cells (>200 µg/mL). They are potential candidates for antileishmanial drug development. Compounds 25-27, were active and cytotoxic. Further studies using OPEN ACCESSMolecules 2014, 19 13252 other cell types are needed in order to discriminate whether the toxicity shown by these compounds is against tumor or non-tumor cells. The results indicate that compounds containing small alkyl chains show better selectivity indices. Moreover, Michael acceptor moieties may modify both the leishmanicidal activity and cytotoxicity. Further studies are required to evaluate if the in vitro activity against Leishmania panamensis demonstrated here is also observed in vivo.

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“…These compounds exhibit a variety of biological activities such as antiproliferative activity on breast cancer cells [6], antimicrobial activity [7], antileishmanial activity [8], antifungical [9], nitrification inhibitors [10] and some of them are used in the treatment of neoplasic diseases as cytotoxic drugs [11] and in neurodegenerative disorders such as Alzheimer's and Parkinson's [12]. More specifically, furanochalcones derivatives produced from HMF and acetophenones show activities in the treatment of pancreatic cancer [13] and breast cancer [14].…”

Section: Introductionmentioning

confidence: 99%

Chemicals from Biomass: Synthesis of Biologically Active Furanochalcones by Claisen–Schmidt Condensation of Biomass-Derived 5-hydroxymethylfurfural (HMF) with Acetophenones

et al. 2016

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solvent polarity by using a mixture ethanol-water allows obtaining high conversion and high selectivity to furanochalcone using HTc and HTr as catalysts. However, MgO becomes rapidly deactivated which was mainly attributed to structural changes on MgO that is in situ rehydrated into Mg(OH) 2 with low activity for aldol condensations. When the reaction was performed using the homogeneous NaOH catalyst, it was found that their activity is higher than that of the solid catalyst, but the selectivity of the later is 2 clearly better. The results indicate that the active phase of the Al/Mg mixed oxide (HTc) in the ethanol-water medium corresponds to a partially restored hydrotalcite with basic hydroxyl groups. The HTc sample could be applied to the synthesis of a variety of furanochalcones with excellent success, while the catalyst could be reused several reaction cycles without loss of activity.

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Synthesis of chalcone analogues with increased antileishmanial activity

Cited by 230 publications

References 17 publications

Avaliação da atividade leishmanicida in vitro de plantas medicinais

Avaliação da atividade leishmanicida in vitro de plantas medicinais

Synthesis, Leishmanicidal and Cytotoxic Activity of Triclosan-Chalcone, Triclosan-Chromone and Triclosan-Coumarin Hybrids

Chemicals from Biomass: Synthesis of Biologically Active Furanochalcones by Claisen–Schmidt Condensation of Biomass-Derived 5-hydroxymethylfurfural (HMF) with Acetophenones

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