In vivo phase II-enzymes inducers, as potential chemopreventive agents, based on the chalcone and furoxan skeletons

Cabrera, Mauricio; Mastandrea, Ignacio; Otero, Gabriel; Cerecetto, Hugo; González, Mercedes

doi:10.1016/j.bmc.2016.02.041

Cited by 19 publications

(17 citation statements)

References 40 publications

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“…Furoxanyl chalcone ( 68 ) is a heterocycle containing compound that translocated Nrf2 and significantly induced the activities of phase II enzymes in the liver. 285 2′,4′,6′-Tris(methoxymethoxy) chalcone ( 69 ) has been reported to induce the expression of heme oxygenase 1 (HO1). 286 Natural products, e.g., licochalcone 287 and xanthohumol, 288 can also induce phase II enzymes and activate Nrf2 in cells.…”

Section: Medicinal Aspects Of Chalconesmentioning

confidence: 99%

Chalcone: A Privileged Structure in Medicinal Chemistry

et al. 2017

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Privileged structures have been widely used as an effective template in medicinal chemistry for drug discovery. Chalcone is a common simple scaffold found in many naturally occurring compounds. Many chalcone derivatives have also been prepared due to their convenient synthesis. These natural products and synthetic compounds have shown numerous interesting biological activities with clinical potentials against various diseases. This review aims to highlight the recent evidence of chalcone as a privileged scaffold in medicinal chemistry. Multiple aspects of chalcone will be summarized herein, including the isolation of novel chalcone derivatives, the development of new synthetic methodologies, the evaluation of their biological properties, and the exploration of the mechanisms of action as well as target identification. This review is expected to be a comprehensive, authoritative, and critical review of the chalcone template to the chemistry community.

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Section: Medicinal Aspects Of Chalconesmentioning

confidence: 99%

Chalcone: A Privileged Structure in Medicinal Chemistry

et al. 2017

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“…A series of furoxan‐based chalcone hybrids was synthesized through Wittig reaction of polymer‐supported phosphonium ylides 37 a – c with furoxancarbaldehydes 26 a , b (Scheme ). The resulting derivatives 39 a , b are not mutagenic and can be considered promising in vivo phase II enzyme inducers, which is very useful in chemopreventive cancer therapy …”

Section: Synthesis No‐donor Properties and Pharmacological Activitmentioning

confidence: 99%

“… Synthesis of furoxanylchalcone hybrids . Reagents and conditions : a) furoxancarbaldehyde 26 a , b , THF, RT, 3–30 h, 52–99 %.…”

Section: Synthesis No‐donor Properties and Pharmacological Activitmentioning

confidence: 99%

“…The resulting derivatives 39 a,b are not mutagenic and can be considered promisingi nvivop hase II enzyme inducers,w hich is very useful in chemopreventive cancer therapy. [38] Various furoxan sulfonamide hybrids with various substituents at C4 in the furoxan cycle were synthesized and evaluated as inhibitors of human catalytically active carbonic anhydrase (hCA) isoforms. Initial 3-phenyl-4-nitrofuroxan 15 b was converted into the p-chlorosulfonyl derivative 40,w hich was easily transformed into the sulfonamide 41 by the action of aconcentrated ammonia solution.…”

Section: Introductionmentioning

confidence: 99%

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Molecular Hybridization Tools in the Development of Furoxan‐Based NO‐Donor Prodrugs

Ферштат

Махова

2017

ChemMedChem

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The molecular hybridization of different compounds with known pharmacological activity is a particularly prominent approach for the design of potential drugs with improved pharmacokinetic profiles. Much attention over the last decade has been focused on the synthesis of hybrid structures with a nitric oxide (NO)-donor framework, as NO is a ubiquitous and crucial regulator of cellular metabolism, affecting various physiological and pathophysiological processes. 1,2,5-Oxadiazole 2-oxides (furoxans), which are capable of exogenous NO release in the presence of thiol cofactors, are an important class of prospective NO donors. As such, a wide range of hybrid compounds that combine a furoxan ring with various pharmacologically active structures have been created. This review focuses on recent results in the synthesis and pharmacological activity of furoxan-based hybrids. Special attention is given to chemo- and regioselective methods used in the preparation of these hybrid structures, and the role of synergistic effects on their pharmacological activity, associated with the furoxan fragment.

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“…For this purpose, different chemical entities have been used, i.e., CuSO 4 , surface-active chemicals, ionophores, triazine, lipids, saponins, and tannins. For almost 20 years, our research group has been working on the development and biological evaluation of different N -oxide-containing aromatic heterocycles [13,14,15,16,17,18]. Among the most relevant biological activities, we have found anti-protozoa activity in phenazine dioxide [19], quinoxaline dioxide [20], indazole N -oxide [21], benzofuroxan [22,23], benzimidazole dioxide [24], and furoxan derivatives [23,25].…”

Section: Introductionmentioning

confidence: 99%

Identification of N-Oxide-Containing Aromatic Heterocycles as Pharmacophores for Rumen Fermentation Modifiers

et al. 2019

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Different strategies have been used to mitigate greenhouse gas emissions from domesticated ruminants, including the removal of protozoa (defaunation). The objective of the present work was to analyze the potential of different N-oxide-containing aromatic heterocycles with known antiprotozoal activity as rumen-gas-abating agents. Nineteen pure compounds, belonging to seven different N-oxide chemotypes from our chemo-library were studied together with monensin in an in vitro rumen simulation assay. Fermentation profiles, i.e., gas production, pH, and short carboxylic acid concentrations, were compared to an untreated control at 96 h post inoculation. In our study, we investigated whole-ruminal fluid, with and without compound treatments, by NMR spectroscopy focusing on concentrations of the metabolites acetate, propionate, butyrate, and lactate. From data analysis, three of the compounds from different N-oxide chemotypes, including quinoxaline dioxide, benzofuroxan, and methylfuroxan, were able to diminish the production of gases such as monensin with similar gas production lag times for each of them. Additionally, unlike monensin, one methylfuroxan did not decrease the rumen pH during the analyzed incubation time, shifting rumen fermentation to increase the molar concentrations of propionate and butyrate. These facts suggest interesting alternatives as feed supplements to control gas emissions from dairy ruminants.

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In vivo phase II-enzymes inducers, as potential chemopreventive agents, based on the chalcone and furoxan skeletons

Cited by 19 publications

References 40 publications

Chalcone: A Privileged Structure in Medicinal Chemistry

Chalcone: A Privileged Structure in Medicinal Chemistry

Molecular Hybridization Tools in the Development of Furoxan‐Based NO‐Donor Prodrugs

Identification of N-Oxide-Containing Aromatic Heterocycles as Pharmacophores for Rumen Fermentation Modifiers

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