A REVIEW ON CHALCONES SYNTHESIS AND THEIR BIOLOGICAL ACTIVITY

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ABOUT AUTHORS
Shipra Vermaa, Alok Kumar Srivastava*1, O.P. Pandeyb
1Department of Chemistry, Mahatma Gandhi P. G. College, Gorakhpur, U.P., India
2Department of Chemistry, D.D.U. Gorakhpur University, Gorakhpur, U.P., India

*sdevender350@gmail.com

ABSTRACT
Chalcones are a valuable molecule of medicinal importance due to presence of reactive ketoethylenic group –CO–CH=CH–, belonging to the flavonoid family. These reactive α,β-unsatutated keto function in chalcones are  responsible for their biological activity. Chalcone can be synthesized by several methods using aldehydes and ketones as starting material. This review is focused about different methods of synthesis and versatile biological activity of chalcones including antimicrobial, anticancer, antioxidant, antimalarial, antituberculosis etc.

Reference Id: PHARMATUTOR-ART-2566

PharmaTutor (Print-ISSN: 2394 - 6679; e-ISSN: 2347 - 7881)

Volume 6, Issue 2

Received On: 22/12/2017; Accepted On: 22/12/2017; Published On: 01/02/2018

How to cite this article: Verma S, Srivastava AK, Pandey OP; A Review on Chalcones Synthesis and their Biological Activity; PharmaTutor; 2018; 6(2); 22-39; http://dx.doi.org/10.29161/PT.v6.i2.2018.22

INTRODUCTION
Chalcone is an α,β- unsaturated ketone and central core for a variety of important biological compounds, which are known as chalcones. Benzylideneacetophenone is an important member of the chalcone series. Chemically these are 1,3-diphenyl-2-propene-1-one, in which two aromatic rings are linked by a three carbon keto-ethylinic system. Chalcones are also present in nature and can be obtained from plant species like Angelica, Glycyrrhiza, Humulus and Scutellaria, which are widely used as traditional folk remedies. Chalcones are an important intermediates for the biosynthesis of flavonoids. Besides the biological activity of chalcones like anti-inflammatory, antimitotic, anti-leishmanial, anti-invasive, anti-tuberculosis, anti-fungal, anti-malarial, anti-tumor, and anti-oxidant it is also recognized for its synthetic utility to prepare pharmacologically-interesting heterocyclic systems like pyrazolines, which have also been largely studied owing to their pharmacological activities, includes anti-tumor anti-inflammatory, anti-parasitary, anti-depressive, anticonvulsant, antimicrobial, antinociceptives and nitric oxide synthase inhibitors.

Chalcone as an antimicrobial agent
A novel 1-(4-butoxy-2-hydroxy phenyl)-3-(2,5 dimethoxyphenyl) prop-2-en-1-one VIII was synthesized as antimicrobial agent. (Barot et al., 2013)

Chalcones V (1-9) were synthesized by Claisen-Schmidt condensation of methyl ketones with several aromatic aldehydes in presence of aqueous solution of sodium hydroxide using microwave irradiations having antibacterial activities. (Bhuiyan et al., 2011)

MWI = Microwave irradiation

Antimicrobial chalcones IV (1-10) were synthesized by condensing benzaldehyde derivatives with acetophenone derivatives in dilute ethanolic sodium hydroxide solution at room temperature according to Claisen –Schmidt condensation. (Choudhary et al., 2011)

 

Chalcones VII (1-6) having antimicrobial activity, were synthesized by condensing either 1-acetylnaphthalene or substituted 1-acetylnaphthalenes with 1-naphthaldehyde or 4-dimethylamino-1 naphthaldehyde in ethanolic NaOH solutions. (Davood and Maseud, 2013)

Chalcones I (1-6) were synthesized by condensing 2-acetyl pyridine with aldehyde derivatives in dilute ethanolic potassium hydroxide solution at room temperature according to Claisen-Schmidt condensation. (Prasad et al., 2008)

Chalcones IX were synthesized by Claisen-Schimdt condensation of aromatic aldehydes with    o-hydroxy acetophenone. Chalcone on reaction with catalytic amount of I2 in DMSO gave Flavones having antimicrobial activity. (Rathore et al., 2015)


Chalcones VI (1-9) were synthesized by using different substituted hydroxyl acetophenone and quinoline carbaldehyde by Claisen-Schmidt condensatiom to give general 1-[substituted aryl]-3-[substituted hetero aryl]-2-propene-1-ones having antibacterial activity. (Sirsat et al., 2012)

A series of chalcones III (1-11) having antimicrobial activity was prepared by Claisen-Schmidt condensation of acetophenones with aromatic aldehydes in the presence of aqueous solution of potassium hydroxide and ethanol at room temperature. (Tiwari et al., 2010)

A series of chalcones II (1-9) was synthesized by reacting 1-(4-isobutylphenyl) ethanone with different substituted aldehyde by Clasien-Schimidt condensation having antibacterial and antifungal activity. (Turkar et al., 2010)

Venkatesh and his co-workers have reported the synthesis of novel series of 5-[1,3-bis (4- substituted phenyl) prop-2-en-1-ylidene]-2-thioxodihydropyrimidine-4,6(1H, 5H)-diones X, XI, XII. The target compounds were synthesized by the Knoevenagel condensation of different chalcones with thiobarbituric acid using acetic acid as a catalyst in ethanol. These compounds have been found to exhibit antimicrobial activity. (Venkatesh et al., 2016)

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