Solution-phase parallel synthesis of substituted chalcones and their antiparasitary activity against Giardia lamblia

Montes‐Ávila, Julio; Díaz‐Camacho, Sylvia Páz; Sicairos-Félix, Josefina; Delgado‐Vargas, Francisco; Rivero, Ignacio A.

doi:10.1016/j.bmc.2009.02.052

Cited by 43 publications

(25 citation statements)

References 29 publications

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“…Current investigations into the antimicrobial activity of flavonoid compounds have targeted plant extracts, pure compounds, products of their metabolism, and also their synthetic analogues [1]. Nowadays chalcones which are precursors of all groups of flavonoid compounds, are more often recommended to combat different kinds of intestinal parasites that cause food poisoning in humans, for example Giardia lamblia [2]. They are also used as acetylcholinesterase inhibitors in the treatment of neurodegenerative diseases such as Alzheimer's [3].…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues

Stompor

Żarowska

2016

Molecules

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Abstract:The objective of this study was to evaluate the antimicrobial activity of structural analogues of xanthohumol 1, a flavonoid compound found in hops (Humulus lupulus). The agar-diffusion method using filter paper disks was applied. Biological tests performed for selected strains of Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria, fungi (Alternaria sp.), and yeasts (Rhodotorula rubra, Candida albicans) revealed that compounds with at least one hydroxyl group-all of them have it at the C-4 position-demonstrated good activity. Our research showed that the strain S. aureus was more sensitive to chalcones than to the isomers in which the heterocyclic ring C is closed (flavanones). The strain R. rubra was moderately sensitive to only one compound: 4-hydroxy-4'-methoxychalcone 8. Loss of the hydroxyl group in the B-ring of 4'-methoxychalcones or its replacement by a halogen atom (´Cl,´Br), nitro group (´NO 2 ), ethoxy group (´OCH 2 CH 3 ), or aliphatic substituent (´CH 3 ,´CH 2 CH 3 ) resulted in the loss of antimicrobial activity towards both R. rubra yeast and S. aureus bacteria. Xanthohumol 1, naringenin 5, and chalconaringenin 7 inhibited growth of S. aureus, whereas 4-hydroxy-4 1 -methoxychalcone 8 was active towards two strains: S. aureus and R. rubra.

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Section: Introductionmentioning

confidence: 99%

Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues

Stompor

Żarowska

2016

Molecules

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“…13 C-NMR (CDCl 3 ): 176.5 (C(4)); 169.7, 167.9 (CO(5)); CO (7)); 162.2 (C(2)); 151.5 (C(8a)); 146.8 (C(7)); 144.3 (C(5)); 139.1 (C(8)); 131.9 (C(1')); 131.1 (C4')); 129.2 (C(3',5')); 126.2 (C(2',6')); 116.0 (C(4a)); 114.3 (C(6)); 108. These compounds were synthesized as described in [30]. 13 C-NMR (MeOD): 177.8 (C(4)); 162.3 (C(2)); 158.2 (C(7)); 153.9 (C(5)); 151.4 (C(8a)); 138.3 (C(6)); 131.4 (C(1')); 129.3 (C(3',5')); 128.2 (C(2',6')); 125.9(C(4')); 111.9 (C(4a)); 107.0 (C(3)); 96.5 (C(8)); 61.2 (MeOÀC(5)); 60.4 (MeOÀC (6)); 55.7 (MeOÀC (7) General Procedure for the Synthesis of Compounds 7 -9, 12, and 13.…”

Section: Experimental Partmentioning

confidence: 99%

Activities of Wogonin Analogs and Other Flavones against Flavobacterium columnare

Tan

Schrader

Khan

et al. 2015

Chemistry & Biodiversity

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In our on-going pursuit to discover natural products and natural product-based compounds to control the bacterial species Flavobacterium columnare, which causes columnaris disease in channel catfish (Ictalurus punctatus), we synthesized flavone and chalcone analogs, and evaluated these compounds, along with flavonoids from natural sources, for their antibacterial activities against two isolates of F. columnare (ALM-00-173 and BioMed) using a rapid bioassay. The flavonoids chrysin (1a), 5,7-dihydroxy-4'-methoxyflavone (11), isorhamnetin (26), luteolin (27), and biochanin A (29), and chalcone derivative 8b showed strong antibacterial activities against F. columnare ALM-00-173 based on minimum inhibition concentration (MIC) results. Flavonoids 1a, 8, 11, 13 (5,4'-dihydroxy-7-methoxyflavone), 26, and 29 exhibited strong antibacterial activities against F. columnare BioMed based upon MIC results. The 24-h 50% inhibition concentration (IC50 ) results revealed that 27 and 29 were the most active compounds against F. columnare ALM-00-173 (IC50 of 7.5 and 8.5 mg/l, resp.), while 26 and 29 were the most toxic compound against F. columnare BioMed (IC50 of 9.2 and 3.5 mg/l, resp.). These IC50 results were lower than those obtained for wogonin against F. columnare ALM-00-173 and F. columnare BioMed (28.4 and 5.4 mg/l, resp.). However, based on MIC results, none of the compounds evaluated in this study were as active as wogonin (MIC 0.3 mg/l for each F. columnare isolate). Further modification of the wogonin structure to enhance antibacterial is of interest.

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“…Chalcone-triazolecoumarin hybrids were reported by Pingaew et al as anticancer and antimalarial agents [10]. It has been reported that chalcones possess many important biological activities including anti-oxidant [11], anticancer [12], anti-bacterial [13], anti-fungal [14], antiparasitic [15], antivascular [16] and anti-inflammatory [17]. Recently Tatiana et al reported the anticancer activities of chalcone and flavonol derivatives [18].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Cytotoxic Activity of New Chalcones and their Flavonol Derivatives

Kotha¹,

Kulkarni²,

Garige³

et al. 2017

Med chem

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A series of chalcones and respective flavonols have been synthesized to explore their anti-cancer activities. All the chalcones were synthesized by the reaction between aldehydes and substituted acetophenones in typical base carried Claisen-Schmidt condensation and their corresponding flavonols were synthesized by hydrogen peroxide oxidized Flynn-Algar-Oymada epoxidation and cyclization. The synthesized compounds were characterized by FTIR, 1 H NMR, 13 C NMR and Mass spectrometry and subjected for cytotoxicity test on MCF-7, HT-29 and HeLa cell lines. Maximum number of compounds demonstrated anti-proliferative activity with IC 50 in the range of 18.67-174.3 μM. Compound 3h with a chloro group and 1-phenyl-3(4-methoxy phenyl )-4-pyrazolyl moiety and the flavonol 4a with 3-thienyl group were found to be most potent compounds among all the tested compounds against MCF-7 cell lines with IC 50 18.67 and 23.79 μM respectively. The most active compound 3h also showed high docking score of -8.825.

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Solution-phase parallel synthesis of substituted chalcones and their antiparasitary activity against Giardia lamblia

Cited by 43 publications

References 29 publications

Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues

Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues

Activities of Wogonin Analogs and Other Flavones against Flavobacterium columnare

Synthesis and Cytotoxic Activity of New Chalcones and their Flavonol Derivatives

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