4'-Acetamidochalcone Derivatives as Potential Antinociceptive Agents

Buzzi, Fátima de Campos; Padaratz, Pâmela; Meira, Aleandra V.; Corrêa, Rogério; Nunes, Ricardo José; Cechinel‐Filho, Valdir

doi:10.3390/12040896

Cited by 30 publications

(12 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The most active compound 97f caused dose-related inhibition in the writhing test, being about 32 to 34-fold more potent than the standard drugs. It was also effective in the second phase of the formalin test and the capsaicin test [116]. A majority of a series of 17 synthetic chalcones demonstrated significant antinociceptive activity when given intraperitoneally, against acetic acid-induced abdominal constructions in mice.…”

Section: Miscellaneous Bioactivitiesmentioning

confidence: 98%

Trends in Utilization of the Pharmacological Potential of Chalcones

Batovska

Todorova²

2010

CCP

287

201

View full text Add to dashboard Cite

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.

show abstract

Section: Miscellaneous Bioactivitiesmentioning

confidence: 98%

Trends in Utilization of the Pharmacological Potential of Chalcones

Batovska

Todorova²

2010

CCP

287

201

View full text Add to dashboard Cite

show abstract

“…Chemistry Synthesis of the reported intermediates; I [27], II [28], III and IV [29], VIa [30], VIb [31], VIIa [32], VIIb [33], VIIc [34], VIId [32],VIIe [35], VIIIb, IXb [36], XIa, XIb [37], XIc [38], XId and XIe [39], XIIa [40], XIIb [41], XIIc [42], XIId [43], XIIe [44], XIIIa [45], XIIIb [46], XIVa [46], XIVb [47], XIVc [48], XIVd [49] and XIVe [50] were performed according to the corresponding reported procedures outlined in Schemes 1-3. The new intermediates (VIIIa, c, d, e) were prepared by a similar method for preparing VIIIb [37], by hydrocyanation of the appropriate substituted cinamoylacetanilides (VIIa, c-e) by acetone cyanohydrin.…”

Section: Resultsmentioning

confidence: 99%

Ligand design, synthesis and biological anti-HCV evaluations for genotypes 1b and 4a of certain 4-(3- & 4-[3-(3,5-dibromo-4-hydroxyphenyl)-propylamino]phenyl) butyric acids and 3-(3,5-dibromo-4-hydroxyphenyl)-propylamino-acetamidobenzoic acid esters

Ismail

Abouzid

Mohamed

et al. 2013

Journal of Enzyme Inhibition and Medicinal Chemistry

View full text Add to dashboard Cite

4-(4-[N-1-carboxy-3-(3,5-dibromo-4-hydroxyphenyl)-3-oxo-propylamino]phenyl)-4-oxo-butyric acid (V), 4-(3- & 4-[N-1-carboxy-3-(3,5-dibromo-4-hydroxyphenyl)-3-oxo-propylaminophenyl]-2-aryl-4-oxo-butyric acids (Xa-e) and 4-(2-alkyl-2-[N-3-(3,5-dibromo-4-hydroxyphenyl)-1-carboxy-3-oxo-propylamino]acetamido) benzoate esters (XVa-e) were designed, synthesized and biologically evaluated as anti-HCV for genotypes 1b and 4a. The design was based on their docking scores with HCV NS3/4A protease-binding site of the genotype 1b (1W3C), which is conserved in the genotype 4a structure. The docking scores predicted that most of these molecules have higher affinity to the HCV NS3/4A enzyme more than Indoline lead. These compounds were synthesized and evaluated for their cytopathic inhibitory activity against RAW HCV cell cultures of genotype 4a and also examined against Huh 5-2 HCV cell culture of genotype 1b, utilizing Luciferase and MTS assays. Compounds Xa and Xb have 95 and 80% of the activity of Ribavirin against genotype 4a and compounds XVa, XVb and XVd exerted high percentage inhibitory activity against genotype 1b equal 87.7, 84.3 and 82.8%, respectively, with low EC50 doses.

show abstract

“…The privileged scaffold chalcone remained a fascination among researchers in the 21st Century due to its simple chemistry, ease of synthesis, diversity of substituents, wide range of biological activities such as anti-diabetic [16], anti-neoplastic [17], antihypertensive [18], anti-retroviral [19], anti-inflammatory [20], anti-parasital [21], anti-histaminic [22], anti-malarial [23], antioxidant [24], anti-fungal [25], anti-obesity [26], anti-platelet [27], anti-tubercular [28], immunosuppressant [29], anti-arrhythmic [30], hypnotic [31], anti-gout [32], anxiolytic [33], anti-spasmodic [34], anti-nociceptive [35], hypolipidemic [36], anti-filarial [37], anti-angiogenic [38], anti-protozoal [39], anti-bacterial [40], antisteroidal [41], etc. The term "chalcone" was coined by Kostanecki, who synthesized a series of natural chromophoric products for the first time.…”

Section: Chalconesmentioning

confidence: 99%