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Synthesis of Heterocyclic-Substituted Chromones and Chalcones

Synthesis of Some Novel Fused Heterocyclic Compounds Derivatives from Bis-chalcones

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Synthesis of Heterocyclic-Substituted Chromones and Chalcones.

AB - Heterocyclic chalcones containing halogenated thiophenes were synthesized. The first step was to synthesize 3-acetyl-2,5-dichlorothiophene and 2-acetyl-5-chlorothiophene as heterocyclic ketones by using Friedel-Crafts acylation. The ketones were then used to synthesize thiophene chalcones through Claisen-Schmidt reaction with the respective heterocyclic aldehydes such as 5-bromothiophene-2-carbaldehyde, 3-methyl-2-thiophene carboxaldehyde and 2-thiophene carboxaldehyde with 3-acetyl-2,5-dichlorothiophene or 2-acetyl-5-chlorothiophene in presence of basic medium, sodium hydroxide to form the corresponding chalcones. Structures of the synthetic compounds were confirmed by IR, MS, 1H and 13C NMR spectral data.

Abstract Synthesis of some Heterocyclic Compounds Derived from Chalcones Author(s): Mohamed J

Chalcones are the principal precursors for the biosynthesis of flavonoids and isoflavonoids. A three carbon α, β-unsaturated carbonyl system constitutes chalcones. Chalcones are the condensation products of aromatic aldehyde with acetophenones in attendance of catalyst. They go through an assortment of chemical reactions and are found advantageous in synthesis of pyrazoline, isoxazole and a variety of heterocyclic compounds. In synthesizing a range of therapeutic compounds, chalcones impart key role. They have showed worth mentioning therapeutic efficacy for the treatment of various diseases. Chalcone based derivatives have gained heed since they own simple structures, and diverse pharmacological actions. A lot of methods and schemes have been reported for the synthesis of these compounds. Amongst all, Aldol condensation and Claisen-Schmidt condensation still grasp high up position. Other distinguished techniques include Suzuki reaction, Witting reaction, Friedel-Crafts acylation with cinnamoyl chloride, Photo-Fries rearrangement of phenyl cinnamates etc. These inventive techniques utilize various catalysts and reagents including SOCl2 natural phosphate, lithium nitrate, amino grafted zeolites, zinc oxide, water, Na2CO3, PEG400, silicasulfuric acid, ZrCl4 and ionic liquid etc. The development of better techniques for the synthesis of α, β- unsaturated carbonyl compounds is still in high demand. In brief, we have explained the methods and catalysts used in the synthesis of chalcones along with their biological activities in a review form to provide information for the development of new-fangled processes targeting better yield, less reaction time and least side effects with utmost pharmacological properties.

six and seven-membered heterocyclic compounds.

Synthesis of New Heterocyclic Di Bromo Chalcone and Quinoxaline Compounds and Their Antibacterial Activity

The chalcone skeleton (1,3-diphenyl-2-propen-1-one) is a unique template that is associated with various biological activities. We synthesized Mannich bases of heterocyclic chalcones (9-47) using a one-step Claisen-Schmidt condensation of heterocyclic aldehydes with Mannich bases of acetophenones, and tested the target compounds for cytotoxicity against three human cancer cell lines (prostate, PC-3; breast, MCF-7; nasopharynx, KB) and a multi-drug resistant subline (KB-VIN). Out of the 39 chalcones synthesized, 31 compounds showed potent activity against at least one cell line with IC50 values ranging from 0.03 to 3.80 μg/mL. Structure-activity relationships (SAR) are also discussed.

N2 - The chalcone skeleton (1,3-diphenyl-2-propen-1-one) is a unique template that is associated with various biological activities. We synthesized Mannich bases of heterocyclic chalcones (9-47) using a one-step Claisen-Schmidt condensation of heterocyclic aldehydes with Mannich bases of acetophenones, and tested the target compounds for cytotoxicity against three human cancer cell lines (prostate, PC-3; breast, MCF-7; nasopharynx, KB) and a multi-drug resistant subline (KB-VIN). Out of the 39 chalcones synthesized, 31 compounds showed potent activity against at least one cell line with IC50 values ranging from 0.03 to 3.80 μg/mL. Structure-activity relationships (SAR) are also discussed.

Structures of the synthetic compounds were confirmed by IR, ..

Synthesis and characterization of heterocyclic chalcones containing halogenated thiophenes.

INTRODUCTION: Heterocyclic compounds belong from medicinally valuable family of organic compounds. Fused ring heterocycles are also important constituents of many available therapeutics agents. Naturally heterocyclic aromatic compounds are widely distributed in animal and plant tissues. More than 90% of new drugs contains heterocyclic ring 1. Heterocyclic compounds possess diversified biological activities, because they are having ability to bind reversibly to proteins. Medicinal chemistry involves great utilization of heterocyclic compounds by converting them into potent biological agents. Recently many researchers work to synthesize and screen fused heterocyclic compounds against a variety of different receptors, yielding several active compounds.

Heterocyclic chalcones containing halogenated thiophenes were synthesized. The first step was to synthesize 3-acetyl-2,5-dichlorothiophene and 2-acetyl-5-chlorothiophene as heterocyclic ketones by using Friedel-Crafts acylation. The ketones were then used to synthesize thiophene chalcones through Claisen-Schmidt reaction with the respective heterocyclic aldehydes such as 5-bromothiophene-2-carbaldehyde, 3-methyl-2-thiophene carboxaldehyde and 2-thiophene carboxaldehyde with 3-acetyl-2,5-dichlorothiophene or 2-acetyl-5-chlorothiophene in presence of basic medium, sodium hydroxide to form the corresponding chalcones. Structures of the synthetic compounds were confirmed by IR, MS, 1H and 13C NMR spectral data.

26/12/2017 · Synthesis and cytotoxic activities of some heterocyclic chalcones
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  • Synthesis, characterization, antifungal activities and ..

    18/12/2012 · Synthesis and biologic activities of some novel heterocyclic chalcone derivatives

  • Crystal structure of the compounds ..

    while compounds 11, ..

  • 26/11/2012 · Journal of Chemistry is a ..

    Heterocyclic Compounds ..

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several series of heterocyclic compounds possessing a ..


Elarfi et al, reported Chalcone derivatives were synthesized by reaction of some benzaldehyde derivatives with acetophenone, then the products obtained were allowed to react with urea, thiourea and hydroxylamine, to give the heterocyclic derivatives of oxazine, thiazine and isoxazole, respectively. The final products have been characterized by elemental analysis, IR and proton NMR spectra. These compounds were also screened for their antibacterial activities 35.

We synthesized Mannich bases of heterocyclic chalcones ..

Kategaonkar et al, reported an efficient and novel one-pot synthesis of new 3, 4-dihydro-3-substituted-2H-naphtho[2,1-e][1,3]oxazine derivatives from 1-naphthol, various anilines and formalin at room temperature grinding is presented. The six-membered N, O-heterocyclic skeleton was constructed via zirconyl(IV) chloride promoted Mannich type reaction. In vitro antimicrobial activities of synthesized compounds have been investigated against Gram-positive Bacillus subtilis, Gram negative Escherichia coli and two fungi Candida albicans and Aspergillus niger in comparison with standard drugs. The results of preliminary bioassay indicate that some of title compounds possess significant antibacterial and antifungal activity 33.

Synthesis of some Heterocyclic Compounds Derived …

A series of heterocyclic chalcone (3a–e, 5, 7) were synthesized and characterized by Infrared, 1H and 13C nuclear magnetic resonance, and mass spectra. Crystal structure of 1-(4-iodophenyl)-3-(5-methylfuran-2-yl)prop-2-en-1-one was determined using single crystal X-ray diffraction. All the synthesized compounds were evaluated for their cytotoxic activities on MDA MB 231 and CHO cell by using MTT assay. Compound 3c showed good cytotoxic effect on MDA MB 231 with IC50 values of 9.8 µg/mL.

and Various Catalysts Used for Chalcone Synthesis.

Chalcones are the main precursors for the biosynthesis of flavonoids and isoflavonoids. Chalcones comprise of a three carbon, α, β-unsaturated carbonyl system. These are the condensation products of aromatic aldehyde with acetophenones in the presence of catalyst. They go through a variety of chemical reactions and are found beneficial in synthesis of pyrazoline, isoxazole and an assortment of heterocyclic compounds. Chalcones play pivotal role in synthesizing a range of remedial compounds. They have exhibited impressive curative efficacy for the treatment of numerous diseases. Chalcone based derivatives have gained focus since they possess simple structures and sundry pharmacological actions. A number of techniques and schemes have been reported for the synthesis of these compounds. Amongst all the stated methods, Aldol condensation and Claisen-Schmidt condensation still hold high position. Other renowned techniques include Suzuki reaction, Witting reaction, Friedel-Crafts acylation with cinnamoyl chloride, Photo-Fries rearrangement of phenyl cinnamates etc. These innovative techniques employ various catalysts and reagents including SOCl2 natural phosphate, lithium nitrate, amino grafted zeolites, zinc oxide, water, Na2CO3, PEG400, silicasulfuric acid, ZrCl4 and ionic liquid etc. The development of improved strategies for the synthesis of α, β-unsaturated carbonyl compounds is still in demand. Briefly, we have explained the methods and catalysts used in the synthesis of chalcones in a review form to provide information for the development of new-fangled processes aiming better yield, less reaction time and minimum side effects.

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