Synthesis and anti-inflammatory activity of chalcone derivatives

Herencia, Felipe; Ferrándiz, Marı́a Luisa; Úbeda, Amalia; Domínguez, José N.; Charris, Jaime; Lobo, Gricela; Alcaráz, María Jesús

doi:10.1016/s0960-894x(98)00179-6

Cited by 195 publications

(117 citation statements)

References 8 publications

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“…35) Synthesis of the title compounds (1a-s, 2a-s), was based on Claisen-Schmidt condensation. 36,37) For this purpose, the prepared formyl quinolines were condensed with commercially available methyl arylketones (Table 1), in the presence of sodium hydroxide. The Econfiguration was confirmed by X-ray structure of (1p) and two more chalcones (1k, 1m) which were already reported.…”

mentioning

confidence: 99%

Antimicrobial and Antileishmanial Studies of Novel (2E)-3-(2-Chloro-6-methyl/methoxyquinolin-3-yl)-1-(Aryl)prop-2-en-1-ones

et al. 2010

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Thirty eight heterocyclic chalcones were synthesized by condensing formylquinolines with diverse methyl arylketones. The target compounds were characterized by spectroscopic techniques (NMR, IR, MS) and elemental analysis. The X-ray crystallographic study of (2E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)prop-2-en-1-one (1p) was also performed for the structure confirmation. The title compounds were screened for anti-microbial and antileishmanial activities. The compounds 1c-e, 1g, 1j-m, 1p, 1r-s, 2g, 2j-p, and 2r-s were found potentially active antileishmanial agents, while 1f-i, 1l, 1o-p, 2f-i, 2l, and 2o-p showed remarkable antibacterial activity. Only compounds 1g and 2g-h exhibited significant antifungal activity.

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confidence: 99%

Antimicrobial and Antileishmanial Studies of Novel (2E)-3-(2-Chloro-6-methyl/methoxyquinolin-3-yl)-1-(Aryl)prop-2-en-1-ones

et al. 2010

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“…10,11) The main mode likely involves a similar metalinduced free-radical formation leading to induce apoptosis in cancer cells and inhibit the tumor angiogenesis. [12][13][14][15][16] Recently, considerable attention has been focused on chalcones, which are a class of privileged structures that are easily prepared and have a wide range of biological properties, [17][18][19][20][21] which makes them an attractive pharmacophoric scaffold. An area of particular interest is their potential as antitumor agents, for which several modes of action have been proposed.…”

Section: )mentioning

confidence: 99%

Design, Synthesis and Antitumor Activity of Novel Artemisinin Derivatives Using Hybrid Approach

Xie

Zhai

Ren

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Despite cancer chemotherapy has entered a new era of molecularly targeted therapeutics and some forms of cancer have been successfully treated by modern therapies, the successful treatment of cancer remains a significant challenge in the future because chemotherapy is limited by the drug resistance and adverse side effects.1) In order to develop more effective and reliable anticancer agents that circumvent these limitations, the search for novel anti-tumor agents has turned to natural products, in particular plants used in traditional folk medicines. 2)In recent years, artemisinin and its derivatives have been widely studied for their anticancer activities. Some of them showed excellent anti-tumor activity toward different cancer cell lines in vitro. [3][4][5][6][7][8][9] Also, several studies demonstrated that artemisinin analogues were effective to many drug-and radiation-resistant cancer cell lines due to their multiple mechanisms. 10,11) The main mode likely involves a similar metalinduced free-radical formation leading to induce apoptosis in cancer cells and inhibit the tumor angiogenesis. [12][13][14][15][16] Recently, considerable attention has been focused on chalcones, which are a class of privileged structures that are easily prepared and have a wide range of biological properties, [17][18][19][20][21] which makes them an attractive pharmacophoric scaffold. An area of particular interest is their potential as antitumor agents, for which several modes of action have been proposed. The key mechanism is the inhibition of tubulin polymerization, while also including the inhibition of angiogenesis and the induction of apoptosis. [22][23][24] Chalcones and artemisinin analogues represent two classes of natural products, whose antitumor effects appear to be consistent via different molecular mechanisms. As the application of hybrid strategy to synthesize artemisinin analogues are continuously emerging, 9,25) it is reasonable to combine their structure analogues to form a single molecular framework with a linker, which would allow us to find more potent anti-tumor agents, in which these 'merge' pharmacophore may be addressing the active site of different targets and offering the possibility to overcome drug resistance. Intrigued by these observations, we designed and synthesized two new series of novel artemisinin derivatives by replacement of oxygen at C-10 with nitrogen, in which the substituted chalcone group is bonded to the artemisinin nucleus through an oxyacetyl linkage.Chemistry The synthetic routes of compounds are outlined in Chart 1. Separable diastereomeric mixture of 10b-azidodihydroartemisinin (2) and 10a-azidodihydroartemisinin (3) were obtained by treating 1 with trimethylsilyl chloride, sodium azide and sodium iodide at room temperature for 28 h, according to ref 6. The a and b isomers appeared as two distinct spots on TLC and were separated by column chromatography, with b-isomers as the major products. The reduction of azido compounds (2, 3) with Staudinger reaction afforded the correspondin...

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“…Chalcones exhibit diverse pharmacological activities, including anti-inflammatory (Abraham et. al 2003), ( Herencia et. al 1998 ), antimitotic (Ko et.al 2003 ), antitubercolosis ( Lin et.…”

Section: Introductionmentioning

confidence: 97%

Synthesis of Nitrogen-Containing Chalcone Via One-Pot Three-Component Reaction . part ii

Abualreish¹,

Ljaleel²,

Fadul³

et al. 2014

IJAC

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The compound 3-Hydroxy-4'-methoxychalcone (1) was prepared by reacting 3-hydroxybenzaldehyde with 4-methoxyacetophenone.The aminomethylation of this chalcone was accomplished by reaction with formaldehyde and N-methylpiperazine in dry acetonitrile to Obtain 3-hydroxy-4'-methoxy-4-(N-methyl-piperazinomethyl) chalcone (2) and 3-hydroxy-4'-methoxy-2,4-bis-(N-methylpiperazinomethyl)chalcone(3). The products were purified by column and thin layer chromatography and were identified along with their intermediates by spectroscopic methods: UV, IR, NMR and mass spectrometry.

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Synthesis and anti-inflammatory activity of chalcone derivatives

Cited by 195 publications

References 8 publications

Antimicrobial and Antileishmanial Studies of Novel (2E)-3-(2-Chloro-6-methyl/methoxyquinolin-3-yl)-1-(Aryl)prop-2-en-1-ones

Antimicrobial and Antileishmanial Studies of Novel (2E)-3-(2-Chloro-6-methyl/methoxyquinolin-3-yl)-1-(Aryl)prop-2-en-1-ones

Design, Synthesis and Antitumor Activity of Novel Artemisinin Derivatives Using Hybrid Approach

Synthesis of Nitrogen-Containing Chalcone Via One-Pot Three-Component Reaction . part ii

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