Antimalarial Activity of Newly Synthesized Chalcone Derivatives <i>In Vitro</i>

Yadav, Neesha; Dixit, Sandeep Kumar; Bhattacharya, Amit; Mishra, Lokesh C.; Sharma, Manish; Awasthi, Satish Kumar; Bhasin, Veena

doi:10.1111/j.1747-0285.2012.01383.x

Cited by 124 publications

(76 citation statements)

References 22 publications

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“…13 Diphenyl propenones (chalcones), however, also exhibit antimalrial activity, 7,14−22 and malaria trophozoite cysteine protease has been proposed as possible target for this class of compound. 14,18 Phenyl urenyl chalcones also exhibit antimalrail activity via multiple mechanisms. 7 Inspired by the above facts we thought to design and synthesize compounds based on sugars having C-linked phenyl propenone moiety and diphenyl urea units together to get hitherto unreported antimalarial agents (Figure 1).…”

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confidence: 99%

Identification of Novel Phenyl Butenonyl C-Glycosides with Ureidyl and Sulfonamidyl Moieties as Antimalarial Agents

Ramakrishna

Gunjan

Shukla

et al. 2014

ACS Med. Chem. Lett.

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A new series of C-linked phenyl butenonyl glycosides bearing ureidyl(thioureidyl) and sulfonamidyl moieties in the phenyl rings were designed, synthesized, and evaluated for their in vitro antimalarial activities against Plasmodium falciparum 3D7 (CQ sensitive) and K1 (CQ resistant) strains. Among all the compounds screened the Clinked phenyl butenonyl glycosides bearing sulfonamidyl moiety (5a) and ureidyl moiety in the phenyl ring (7d and 8c) showed promising antimalarial activities against both 3D7 and K1 strains with IC 50 values in micromolar range and low cytotoxicity offering new HITS for further exploration.

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confidence: 99%

Identification of Novel Phenyl Butenonyl C-Glycosides with Ureidyl and Sulfonamidyl Moieties as Antimalarial Agents

Ramakrishna

Gunjan

Shukla

et al. 2014

ACS Med. Chem. Lett.

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“…Treatment of alcohol 4 with triphenylphosphine and tribromoisocyanuric acid [19] in dichloromethane at room temperature for 4 h produced the desired bromide intermediate (5). Coupling of bromide 5 with apocynin (6) in presence of potassium carbonate in 2-methyltetrahydrofuran at reflux for 1 h gave the desired product 1-(4-((5-nitrofuran-2-yl)methoxy)-3-methoxyphenyl)ethanone (7). Claisen-Schmidt reaction of ethanone 7 with aromatic aldehydes 8A-K was carried out under solvent free conditions using solid NaOH as catalyst at room temperature [20,21] for 5-10 min to afford chalcones 9A-9K in 86-96 % yield.…”

Section: Resultsmentioning

confidence: 99%

“…They are significant as structural motifs among biologically active molecules and also for combinatorial assembly of heterocyclic scaffolds [2][3][4]. Chalcones containing several functional groups showed a wide spectrum of biological activities such as antileishmanial [5,6], antimalarial [5,7], anticancer [8,9], anti-HIV [10], antioxidant [11], inflammatory [12] antiprotozoal [13], antiulcer [14] and antimicrobial [15,16] activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Antiinflammatory Activity of Chalcone Derivatives Linked with Apocynin and 5-Nitrofuran Moiety

Reddy¹,

Kathale²

2018

Asian J. Chem.

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The present paper describes the synthesis of some new chalcone derivatives i.e. 1-[3-methoxy-4-(5-nitro-furan-2-ylmethoxy)-phenyl]-3-(substituted phenyl)-propenone derivatives (9A-9K) from furfural and apocynin as starting materials. Claisen-Schmidt reaction of 1-(4-((5-nitrofuran-2-yl)methoxy)-3-methoxyphenyl)ethanone (7) with aromatic aldehydes (8A-K) under solvent free conditions using solid NaOH as catalyst at room temperature resulted in the formation of chalcone derivatives (9A-9K) in 86-96 % yield. These compounds were characterized by 1 H NMR, Mass and IR spectroscopy and were evaluated for their anti-inflammatory activity.Keywords: Anti-inflammatory activity, Apocynin, Chalcones, Furfural, Synthesis.Asian Journal of Chemistry; Vol. 30, No. 2 (2018), 312-316 Merck pre-coated plates (silica gel 60 F254) were used and spots were visualized under UV light. Merck silica gel 60 (230-400 mesh) was used for flash column chromatography and the eluting solvents are indicated in the procedures. Melting point determinations were performed by using Mel-temp apparatus and are uncorrected. 1H NMR spectra were recorded in Varian MR-400 MHz instrument. The mass spectra were recorded on Agilent ion trap MS and infrared spectra were recorded on a Perkin Elmer FT-IR spectrometer. 5-Nitrofurfural diacetate (2):A premixed solution of concentrated nitric acid (8.6 mL, 12.2 g, 193.62 mmol) and concentrated sulphuric acid (0.06 mL, 1.1 g, 11.2 mmol) was added drop-wise into acetic anhydride (90 mL) at 0 °C with stirring. To the above reaction mixture, furfural (1) (freshly distilled, 10.4 mL, 12.06 g, 125.5 mmol) was added dropwise over a period of 45 min and stirred for 1 h at 0 °C. Water (100 mL) was added to the mixture and stirred at room temperature for 30 min to obtain a white precipitate. To the reaction contents, 10 % NaOH solution was added until the pH of the mixture reached about 2.5 and the mixture was heated at 50°C for 1 h. After cooling to room temperature, the white precipitate formed was filtered, washed with water, recrystallized from anhydrous ethanol and dried to obtain diacetate compound 2. Yield: 24.84 g, 82 %. 5-Nitrofurfural (3):A mixture of 5-nitrofurfural diacetate (2) (10 g, 41.12 mmol) and 50 % aqueous sulphuric acid (100 mL) was heated to 100 °C for 10 min. After completion of the reaction, checked by TLC, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (2 × 100 mL) and the organic layer was washed with water, brine solution and dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain 5-nitrofurfural 3. Yield: 5.10 g, 88 %. m.p.: 35-36 °C.(5-Nitrofuran-2-yl)methanol (4): To a stirred solution of 5-nitrofurfural (3) (5 g, 35.44 mmol) in methanol (100 mL), cooled to 0 °C, was added sodium borohydride (1.47 g, 38.98 mmol) portion-wise and continued to stirred for additional 30 min. After completion of the reaction, checked by TLC, the solvent was concentrated under reduced pressure and the residue was quenched with water (2...

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“…Formation of these nuclei involves cyclization of α-β unsaturated system of chalcones. Chalcones and its analogues have numerous pharmacological activities such as antimicrobial [4,5], antiinflammatory analgesic, antiviral, antioxidant, anticancer, antimalarial, antiprotozoal, anticonvulsant [6][7][8][9][10][11][12][13][14][15] (Figure 1). …”

Section: Introductionmentioning

confidence: 99%

Chalconoid Derived Heterocycles as Potent Bioactive Molecules: A Review

Sapra¹,

Sharma²

2016

Chem Sci J

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Although chalcones symbolize an important pharmacophore for variety of biological actions, however their analogues are also reported to be equally important for plethora of biological actions. In the present review, a comprehensive study of chalcones derived molecules (like pyrazoles, isoxazoles, pyridine, pyrimidine) their pharmacological actions, mechanism of action, structure activity relationship studies have been described. which includes anti-proliferative, anti-inflammatory, antioxidant, proapoptotic, anti-bacterial and anti-adhesive effects [18]. Analogues of chalcones Pyrazoline analogues with various pharmacological activities:Pyrazole nucleus present in compounds exhibit wide range of biological activity. Introduction of a pyrazole ring in the chalcones between the two aryl rings increase the cytotoxic activity against a series of human cancer cell lines. Dhar et al. [19] synthesized a series of 1-acetyl-3,5-diaryl-4,5-dihydro-(H)-pyrazoles and assayed for in vitro cytotoxicity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines, compound 1 showed broad spectrum cytotoxic activity against all the four cell lines. The activity shown by the compounds conclude that (i) Substitution on phenyl ring showed marked effect on cytotoxic activity, (ii) Presence of electron donating groups on phenyl ring led to enhanced activity whereas electron withdrawing group except NO 2 reduces the cytotoxic activity, (iii) Replacement of phenyl ring with heterocyclic ring also reduces the cytotoxic potential and napthyl ring on both sides are more beneficial for cytotoxic potential Chemical Sciences JournalChem ic a l S cience s J o u rnal

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Antimalarial Activity of Newly Synthesized Chalcone Derivatives In Vitro

Cited by 124 publications

References 22 publications

Identification of Novel Phenyl Butenonyl C-Glycosides with Ureidyl and Sulfonamidyl Moieties as Antimalarial Agents

Identification of Novel Phenyl Butenonyl C-Glycosides with Ureidyl and Sulfonamidyl Moieties as Antimalarial Agents

Synthesis, Characterization and Antiinflammatory Activity of Chalcone Derivatives Linked with Apocynin and 5-Nitrofuran Moiety

Chalconoid Derived Heterocycles as Potent Bioactive Molecules: A Review

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