Synthesis and pharmacological activity of chalcones derived from 2,4,6-trimethoxyacetophenone in RAW 264.7 cells stimulated by LPS: Quantitative structure–activity relationships

Chiaradia, Louise Domeneghini; Santos, Rodrigo dos; Vitor, Carlos Eduardo; Vieira, André A.; Leal, Paulo César; Nunes, Ricardo José; Calixto, João B.; Yunes, Rosendo A.

doi:10.1016/j.bmc.2007.10.039

Cited by 56 publications

(37 citation statements)

References 28 publications

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“…This result suggests that the tested compounds can act as inhibitors of inflammatory processes. The quantitative SAR (QSAR) study revealed that electronwithdrawing (EW) substituents in ring B (chlorine and nitro groups) increased the inhibition of NO production, mainly when in position C-2 [33].…”

Section: Anti-inflammatory Activitymentioning

confidence: 99%

Trends in Utilization of the Pharmacological Potential of Chalcones

Batovska

Todorova²

2010

CCP

296

206

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Chalcones (1,3-diaryl-2-propen-1-ones) are open chain flavonoids that are widely biosynthesized in plants. They are important for the pigmentation of flowers and, hence, act as attractants to the pollinators. As flavonoids, chalcones also play an important role in defense against pathogens and insects. A longstanding scientific research has shown that chalcones also display other interesting biological properties such as antioxidant, cytotoxic, anticancer, antimicrobial, antiprotozoal, antiulcer, antihistaminic and anti-inflammatory activities. Some lead compounds with various pharmacological properties have been developed based on the chalcone skeleton. Clinical trials have shown that these compounds reached reasonable plasma concentrations and did not cause toxicity. For these reasons, chalcones became an object of continued interest in both academia and industry. Nowadays, several chalcones are used for treatment of viral disorders, cardiovascular diseases, parasitic infections, pain, gastritis, and stomach cancer, as well as like food additives and cosmetic formulation ingredients. However, much of the pharmacological potential of chalcones is still not utilized. The purpose of this review is to describe the recent efforts of scientists in pharmacological screening of natural and synthetic chalcones, studying the mechanisms of chalcone action and relevant structure-activity relationships. Put together, these activities aimed at synthesis of pharmacologically active chalcones and their analogs.

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Section: Anti-inflammatory Activitymentioning

confidence: 99%

Trends in Utilization of the Pharmacological Potential of Chalcones

Batovska

Todorova²

2010

CCP

296

206

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“…This effort is expected to allow us to understand the relationship between the physicochemical features of a compound with biological activities, and further design the more potentially effective drugs in a rational way. 3D QSAR analysis was applied to correlate the structure of chalcones and its biological activities have been reported (Chiaradia et al, 2008;Liu and Go, 2007;Sivakumar et al, 2007;Xue et al, 2004). However, to the best of our knowledge, no 3D QSAR of chalcone and its NO inhibitory activity, as a preliminary investigation on its potential as anti-inflammatory agent, have not been undertaken.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and QSAR analysis of chalcone derivatives as nitric oxide inhibitory agent

et al. 2011

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In this study, thirty-eight chalcone analogs were synthesized and evaluated for nitric oxide (NO) inhibition activity on RAW 264.7 cells. Among these compounds, chalcones bearing furanyl group showed remarkable anti-inflammatory activity. Both compounds 2d and 2j were identified as the most potent NO inhibitor on IFN-c/LPS-activated RAW 264.7 cells. In order to examine the structure-activity relationship, a 3D QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method on the selected chalcones. Partial least square analysis produced a statistically coherent model with good predictive value, r 2 = 0.989 and a good cross validated value, q 2 = 0.583.

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“…Chalcones were recrystallized from hot ethanol to obtain pure substances at yields between 53% and 98%. The structures of chalcones ( Figure 1) were confirmed through comparisons of their melting points and nuclear magnetic resonance spectra with those previously published for chalcones from A, C and P series (CHIARADIA et al, 2008a), chalcones B (NAVARINI et al, 2009;BORCHHARDT et al, 2010), chalcones D , chalcones J (COSTA et al, 2014), chalcones L and R (CHIARADIA et al, 2012), chalcones M (SALUM et al, 2013), chalcones N (MIELCKE et al, 2012 and chalcones T (CHIARADIA et al, 2008b).…”

Section: Synthesis Of Chalconesmentioning

confidence: 56%

Chalcones to control Alternaria alternata in murcott tangor fruits

Camargos¹,

Perina²,

Carvalho³

et al. 2016

Biosci. J.

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Alternaria brown spot (ABS), caused by the fungus Alternaria alternata pathotype tangerine, is one of the main phytosanitary problems for mandarin growers. About 15 applications per year of harmful fungicides are required for controlling ABS disease in citrus orchards. As chalcones seem to be less toxic to humans and environment than the commercial fungicides in use, this study initially aimed at synthesizing 137 chalcones through aldolic condensations between benzaldehydes and acetophenones. The resulting chalcones were screened for activity against A. alternata through a fungal growth assay that was carried out in 96-cell polypropylene plates, using the same concentration to all studied substances. The four active chalcones underwent conidia germination and mycelial growth, which confirmed the antifungal activity of the compounds. These chalcones were then poured onto Murcott tangor fruit that had been inoculated with conidia of the fungus. All four chalcones reduced the ABS progress to values significantly smaller (P≤0.05) than that observed for the control. Statistical calculations showed that the best results were afforded by two compounds, bearing a 2,4,5-trimethoxyphenyl group at position 3 of prop-2-enal and a 3-nitro-or 3-hydroxyphenyl group at position 1 of the aldehyde. Such compounds reduced the incidence of the disease in Murcott tangor fruit to values that did not differ statistically from those obtained with a commercial fungicide.

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Synthesis and pharmacological activity of chalcones derived from 2,4,6-trimethoxyacetophenone in RAW 264.7 cells stimulated by LPS: Quantitative structure–activity relationships

Cited by 56 publications

References 28 publications

Trends in Utilization of the Pharmacological Potential of Chalcones

Trends in Utilization of the Pharmacological Potential of Chalcones

Synthesis and QSAR analysis of chalcone derivatives as nitric oxide inhibitory agent

Chalcones to control Alternaria alternata in murcott tangor fruits

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