Synthesis and in vitro evaluation of antifungal and cytotoxic activities of eugenol glycosides

Souza, Thiago Belarmino de; Orlandi, Marina; Coelho, Luiz Felipe Leomil; Malaquias, Luiz Cosme Cotta; Dias, Amanda Latércia Tranches; Carvalho, Roberta Ribeiro de; Silva, Naiara Chaves; Carvalho, Diogo Teixeira

doi:10.1007/s00044-013-0669-2

Cited by 38 publications

(21 citation statements)

References 25 publications

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“…The initial goal of this study consisted of the design and synthesis of new eugenol glucosides which could be more potent and less toxic than the peracetyl glucoside 1 and fluconazole. Considering the low water solubility of the prototype (1), we synthesized dihydroxy derivatives (5,(9)(10)(11) to obtain derivatives which had better solubility profile for future in vivo assays with the promising compounds. According to the literature, good drug candidates must show adequate solubility and optimum log P value to result in good solubilization in the biophase when administered orally or by other routes (15).…”

Section: In Vitro Assaysmentioning

confidence: 99%

“…. Moreover, in another work of the same group , the synthesis of eugenol glycosides was reported along with the potential of the eugenol peracetyl glucoside ( 1 , Figure ) against Candida species. One of these results was quite interesting as 1 was shown to be more active (IC 50 3.8 μ m ) than the standard drug (fluconazole) against Candida glabrata , an opportunistic pathogen in many immunocompromised patients.…”

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confidence: 92%

“…Some authors have validated the biological activities of eugenol such as antimicrobial , antiprotozoarial , antioxidant , anti‐inflammatory , anti‐carcinogenic , and anticonvulsant activity . Other works describe the semi‐synthesis of eugenol derivatives and their wide biological potential as antibacterial, antifungal and antiviral agents .…”

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confidence: 99%

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New Eugenol Glucoside‐based Derivative Shows Fungistatic and Fungicidal Activity against Opportunistic Candida glabrata

et al. 2015

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A new series of glucosides modified in their saccharide units were synthesized, evaluated against Candida sp., and compared to prototype 1, an eugenol tetracetyl glucoside previously synthesized and shown to be active against Candida glabrata. Among the new glucosides, benzyl derivative 5 was the most promising, showing fungistatic activity at IC50 18.1 μm against Candida glabrata (threefold higher than fluconazole) and fungicidal activity with a low IC90 value of 36.2 μm. Moreover, the cytotoxic activity of compound 5 (CC50 : 580.9 μm), tested in peripheral blood mononuclear cells, suggests its potential as an agent to treat Candida glabrata infections, with a selectivity index of 32. The new eugenol glucoside 5 may be considered as a novel structural pattern in the development of new anti-Candida drugs.

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Section: In Vitro Assaysmentioning

confidence: 99%

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confidence: 92%

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New Eugenol Glucoside‐based Derivative Shows Fungistatic and Fungicidal Activity against Opportunistic Candida glabrata

et al. 2015

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“…Eugenol is a natural allyl phenol found in the essential oil of cloves ( Syzygium aromaticum ), sassafras ( Ocotea odorifera ) and cinnamon ( Cinnamomum zeylanicum ) and has attracted attention of more researchers, either because of its wide range of biological activities or by chemical versatility of its structure . Among the biological activities already described for eugenol, one can cite analgesic and anti‐inflammatory , anaesthetic , hypotensive , antioxidant , antitumoral , anti‐parasitic and antifungal action .…”

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confidence: 99%

Synthesis and Biological Evaluation of New Eugenol Mannich Bases as Promising Antifungal Agents

et al. 2015

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New Mannich base-type eugenol derivatives were synthesized and evaluated for their anticandidal activity using a broth microdilution assay. Among the synthesized compounds, 4-allyl-2-methoxy-6-(morpholin-4-ylmethyl) phenyl benzoate (7) and 4-{5-allyl-2-[(4-chlorobenzoyl)oxy]-3-methoxybenzyl}morpholin-4-ium chloride (8) were found to be the most effective antifungal compounds with low IC50 values, some of them well below those of reference drug fluconazole. The most significant IC50 values were those of 7 against C. glabrata (1.23 μm), C. albicans and C. krusei (both 0.63 μm). Additionally, the synthesized compounds were evaluated for their in vitro cytotoxic effects on human mononuclear cells. As result, the cytotoxic activity of eugenol in eukaryotic cells decreased with the introduction of the morpholinyl group. Given these findings, we point out compounds 7 and 8 as the most promising derivatives because they showed potency values greater than those of eugenol and fluconazole and they also presented high selectivity indexes.

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“…For instance, remote Wacker-Type oxidation of a Vitamin E succinate derivative proceeded smoothly to give the desired product 4a in 82% yield. Eugenol peracetyl-glucoside 3b having activity against the fungi 52 was also oxidized in 82% yield (4b). In addition, the steroidal substrates 3b-3f synthesized from estrone, epiandrosterone, lithocholic acid, and glycyrrhetinic acid, respectively, were subjected to the oxidation procedure, affording the desired products in 62-86% yields (4b-4f).…”

Section: Resultsmentioning

confidence: 99%

Nickel-catalyzed remote and proximal Wacker-type oxidation

Liu

et al. 2019

Commun Chem

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Wacker oxidation chemistry is widely applied to oxidation of olefins to carbonyls in the synthesis of pharmaceuticals, natural products, and commodity chemicals. However, in this chemistry efficient oxidation of internal olefins and highly selective oxidation of unbiased internal olefins without reliance upon suitable coordinating groups have remained significant challenges. Here we report a nickel-catalyzed remote Wacker-type oxidation where reactions occur at remote and less-reactive sp 3 C-H sites in the presence of a priori more reactive ones through a chain-walking mechanism with excellent regio-and chemo-selectivity. This transformation has attractive features including the use of ambient air as the sole oxidant, naturally-abundant nickel as the catalyst, and polymethylhydrosiloxane as the hydride source at room temperature, allowing for effective oxidation of challenging olefins. Notably, this approach enables direct access to a broad array of complex, medicinally relevant molecules from structurally complex substrates and chemical feedstocks.

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Synthesis and in vitro evaluation of antifungal and cytotoxic activities of eugenol glycosides

Cited by 38 publications

References 25 publications

New Eugenol Glucoside‐based Derivative Shows Fungistatic and Fungicidal Activity against Opportunistic Candida glabrata

New Eugenol Glucoside‐based Derivative Shows Fungistatic and Fungicidal Activity against Opportunistic Candida glabrata

Synthesis and Biological Evaluation of New Eugenol Mannich Bases as Promising Antifungal Agents

Nickel-catalyzed remote and proximal Wacker-type oxidation

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