New nitrochalcones. IX

Széll, T.; Sohár, I.

doi:10.1139/v69-207

Cited by 45 publications

(23 citation statements)

References 10 publications

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“…All compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) were synthesized by a mixture of 2,5-dichloro-3-acetylthiophene (0.001 mol) and the appropriate aryl or heteroaryl aldehyde (0.001 mol) were stirred in methanol (10 mL). To this mixture an aqueous solution of KOH (40%, 5 mL) was added with continuous stirring.…”

Section: General Experimental Methodsmentioning

confidence: 99%

“…6,7,8,9,10,11 The use of several Lewis acids (p-toluene sulfonic acid, B 2 O 3 , RuCl 3 , AlCl 3 , BF 3 and dry HCl) has also been demonstrated. 12,13,14,15,16,17 The most important catalysts were used and listed as solid sodium hydroxide (NaOH) and aqueous NaOH. Andreson et al, in 2001, introduced first time a solid sodium hydroxide method in a hydroxy chalcone derived from cinnamon.…”

Section: 45mentioning

confidence: 99%

“…Then, it was purified by column chromatography and crystallized from a mixture of ethyl acetate and hexane (1:1) (Scheme-I). Reagents and conditions: (i) potassium hydroxide (KOH), (ii) Room temperature condition; (iii) Methanol; The structural group of R in scheme-1 is specified below (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) and the synthesis was carried out with individual type of aromatic or heteroaromatic aldehydes to synthesize various chalcone derivatives with 2,5-dichloro-3-acetylthiopene ring (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) as in the Table 1. The mechanism of formation of novel synthetic chalcone was shown below in Figure 1.…”

Section: Chemistrymentioning

confidence: 99%

“…The MIC was taken as that concentration used in the test tube number just prior to the test tube number labelled where the first sign of growth was observed. This procedure was followed to determine the MIC values for all the compounds of series of new chalcone derivatives with 2,5-dichloro-3-acetylthiopene ring (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20). It is shown in the Table 2.…”

Section: Antifungal Activitymentioning

confidence: 99%

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Synthesis and Biological Activity of Novel 2,5-Dichloro-3-Acetylthiophene Chalcone Derivatives

Lokesh¹,

Prasad²,

Shaik³

2017

IJPER

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Objective: A series of novel 2, 5-dichloro-3-acetylthiophene chalcone derivatives were synthesized by Claisen-Schmidt condensation and evaluated for them in vitro antifungal, antitubercular activities and cytotoxic activity against DU145 (prostate) cancer cell line. Methods: Among all series of synthesized compounds, four compounds were displayed proximity of antifungal activity (MIC ≤ 8.0 µg/mL) towards the fungus species Aspergillus niger (ATCC 6275, An) and Candida tropicalis (ATCC 1369, Ct) and compared against fluconazole standard (MIC ≤ 1.0 µg/mL) by agar-diffusion and tube dilution methods. Results: One compound was shown a promising antimycobacterial activity (MIC∼3.12 µg/mL) correlated with pyrazinamide (MIC∼3.12 µg/mL) and also another five compounds exhibited better activity (MIC∼6.25 µg/mL) towards M. tuberculosis H 37 Rv species. All series of compounds were treated with DU145 cells and tested for cytotoxicity by MTT assay. Among all, one compound was shown similar cytotoxicity activity (IC 50 ∼5±1 µg/ mL) and the other compound was shown closer activity (IC 50 ∼10±2µg/mL) compared with a methotrexate (IC 50 ∼5±1 µg/mL). The spectral studies (FT-IR, Mass, 1 HNMR and 13 CNMR) studies provided new molecular scaffolds with detailed structure-activity relationship. Conclusion: These novel chalcones with thienyl ring structure would be promising new scaffold for establishing specific targets on fungal, mycobacteria species and other cancer cell lines.

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Section: General Experimental Methodsmentioning

confidence: 99%

Section: 45mentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Antifungal Activitymentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and Biological Activity of Novel 2,5-Dichloro-3-Acetylthiophene Chalcone Derivatives

Lokesh¹,

Prasad²,

Shaik³

2017

IJPER

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“…Furthermore, the synthesis of chalcones has been catalyzed by acids such as dry HCl (Széll and Sohár, 1969), BF 3 .OEt 2 (Narender and Papi-Reddy, 2007), RuCl 3 (Iranpoor and Kazemi, 1998), silica-sulfuric acid and acetic acid-sulfuric acid (Thirunarayanan and Vanangamudi, 2007;Konieczny et al, 2007) and paratoluenesulfonic acid (solvent free and under microwave irradiation) (Gall et al, 1999).…”

Section: Introductionmentioning

confidence: 99%

1-Indanone chalcones and their 2,4-Dinitrophenylhydrazone derivatives: Synthesis, physicochemical properties and in vitro antibacterial activity

Fadare¹,

Akinpelu²,

Ejemubu³

et al. 2014

Afr. J. Pure Appl. Chem.

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Chalcones are natural biocides. Several publications appear every year covering the synthesis of chalcones because they exhibit an array of pharmacological activities. In this study, some condensation reactions of 1-Indanone with substituted benzaldehydes were carried out under different reaction conditions. The chalcone products were converted to their corresponding 2,4-Dinitrophenylhydrazone derivatives and evaluated against five gram-positive and eight gram-negative bacteria for their in vitro antibacterial property. Antimicrobial activity was observed against many of the tested strains, with zones of inhibition ranging from 10 to 28 mm. In many cases, the hydrazone derivatives were more active than their chalcone precursors. The best results were obtained against gram-negative bacteria for most of the compounds. Compound 1b was the most active with its minimum inhibitory concentrations (MICs) against six strains of bacteria ranging from 15.6 to 31.3 µg/ml, hence, could be developed as an antibacterial agent against infections caused by some gramnegative bacteria such as Pseudomonas aeruginosa and Salmonella typhimurium.

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Potent Anthelmintic Activity of Chalcones Synthesized by an Effective Green Approach

Turani,

Castro,

Vazzana

et al. 2024

ChemMedChem

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There is currently an urgent need for new anthelmintic agents due to increasing resistance to the limited available drugs. The chalcone scaffold is a privileged structure for developing new drugs and has been shown to exhibit potential antiparasitic properties. We synthesized a series of chalcones via Claisen‐Schmidt condensation, introducing a novel recoverable catalyst derived from biochar obtained from the pyrolysis of tree pruning waste. Employing microwave irradiation and a green solvent, this approach demonstrated significantly reduced reaction times and excellent compatibility with various functional groups. The result was the generation of a library of functionalized chalcones, exhibiting exclusive (E)‐selectivity and high to excellent yields. The chalcone derivatives were evaluated on the free‐living nematode Caenorhabditis elegans. The chalcone scaffold, along with two derivatives incorporating a methoxy substituent in either ring, caused a concentration‐dependent decrease of worm motility, revealing potent anthelmintic activity and spastic paralysis not mediated by the nematode levamisole‐sensitive nicotinic receptor. The combination of both methoxy groups in the chalcone scaffold resulted in a less potent compound causing worm hypermotility at the short term, indicating a distinct molecular mechanism. Through the identification of promising drug candidates, this work addresses the demand for new anthelmintic drugs while promoting sustainable chemistry.

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New nitrochalcones. IX

Cited by 45 publications

References 10 publications

Synthesis and Biological Activity of Novel 2,5-Dichloro-3-Acetylthiophene Chalcone Derivatives

Synthesis and Biological Activity of Novel 2,5-Dichloro-3-Acetylthiophene Chalcone Derivatives

1-Indanone chalcones and their 2,4-Dinitrophenylhydrazone derivatives: Synthesis, physicochemical properties and in vitro antibacterial activity

Potent Anthelmintic Activity of Chalcones Synthesized by an Effective Green Approach

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