Design, Synthesis and
Bio Evaluation of Chalcone
Derivatives as Anti-oxidant and
Anti-inflammatory Agents
Presented By
AASHISH CHAUHAN
ARYAN TYAGI
HARSH SAXENA
Under the Guidance of
Mr. Saurabh Singh
Content
• Introduction 4
• Literature Review 9
• Rationale behind research 11
• Plan of Work 12
Introduction of Chalcone
• Chalcones are open-chain flavonoids characterized by the core
framework 1,3-diphenylprop-2-en-1-one.
• These compounds consist of two aromatic rings (designated as ring A and
ring B) connected by a three-carbon α,β-unsaturated carbonyl system (-
CO-CH=CH-).
• The term "chalcone" was coined by Kostanecki and Tambor and derives
from the Greek word "chalcos" meaning "bronze," reflecting the
characteristic color of many natural chalcones
General Structure of Chalcones
General Structure of Chalcones
• Chalcones have a general structure consisting of two aromatic rings
(often called A and B rings).
• These rings are connected by a three-carbon α,β-unsaturated carbonyl
chain, featuring a carbonyl group (C=O) and a carbon-carbon double
bond (C=C).
• This structure is known as trans-1,3-diphenyl-2-propen-1-one in its most
common form.
• Chalcones exist mainly as trans (E) isomers, as they are more stable.
• The structure allows for substitutions on the rings, leading to formation of
derivatives having anti-inflammatory and anti-oxidant properties
Metochalcone
Claisen-schmidt Reaction
• Claisen-Schmidt reaction is an aldol condensation between an aldehyde
or ketone with α-hydrogens and an aromatic carbonyl without α-
hydrogens.
• The base forms an enolate from the α-hydrogen compound, which attacks
the aromatic carbonyl.
• The intermediate dehydrates to form an α,β-unsaturated carbonyl
compound.
• This reaction is commonly used to synthesize chalcone derivatives by
combining appropriate aromatic aldehydes and acetophenones.
• It efficiently creates the conjugated double bond system central to
chalcones
Benzaldehyde Actophenon Chalcone
Literature Review
Nadia A. A. Elkanziet al. 2022, reviewed that Chalcone derivatives
are prized species because they include the CO-CH-CH- keto-ethylenic
moiety Due to the reactive, unsaturated carbonyl group they contain.
chalcones and its derivatives anti-inflammatory and anti-oxidant
pharmacological actions. The synthesis of chalcone derivatives, which had
been physiologically explored towards specific disease targets, was made
possible by recent advances in heterocyclic chemistry. Significant action was
demonstrated by the pyrazole-chalcone derivative.
A. P. S. Bonacardaret al. 2020, In three phases, produced novel
chalcone sulfonamide derivatives were starting with benzophenones and
aldehydes. Additionally, in four stages, (E)-3-(4-chlorophenyl)-1-(4-methoxy
phenyl) prop-2-en-1-one was transformed to various pyrazolines.
Sulfonamides were synthesised at room temperature without the use of any
solvents, and following a straightforward work-up without the use of any
chromatographic methods for purification, the products were produced in
high purity. The in anti-inflammatory activity of each product was tested.
Determining Anti-Oxidant activity
1. DPPH Assay
• This method uses the stable free radical DPPH, which has a deep violet
color. Antioxidants donate hydrogen atoms to DPPH, reducing it and
causing the solution to lose color.
• The change in color intensity is measured spectrophotometrically,
indicating the compound’s free radical scavenging ability.
2. FRAP Assay
• This method measures antioxidant power by their ability to reduce ferric
ions (Fe3+) to ferrous ions (Fe2+) under acidic conditions.
• The Fe2+ forms a blue-colored complex with TPTZ, whose intensity is
measured at 593 nm, reflecting the sample’s reducing (antioxidant)
capacity
Determining Anti-Inflammatory activity
1. Protein Denaturation Inhibition Assay
• This method measures the ability of a compound to prevent denaturation
of proteins caused by heat or chemicals. Since protein denaturation is a
cause of inflammation, inhibition indicates anti-inflammatory potential.
• The extent of protection is measured spectrophotometrically, reflecting
anti-inflammatory effects.
2. Membrane Stabilization Assay
• This evaluates a compound’s ability to stabilize cell membranes,
preventing lysis of red blood cells under stress. Since membrane
stabilization reduces the release of inflammatory mediators from
lysosomes, higher stabilization shows stronger anti-inflammatory activity.
• The assay measures hemolysis inhibition spectrophotometrically
Rational behind the Work
• The detailed and comprehensive literature survey on the synthesis of
Chalcone derivatives reviled that the appropriate structural manipulation had
resulted in the synthesis of therapeutically active compounds with the
desirable biological action.
• Accordingly, the present research work has been planed to synthesize Chalcone
derivatives by carrying out appropriate structural manipulation to obtain derivatives with
desired activity.
•It was planned to attempt the synthesis of a series of Chalcone derivatives so that the therapeutic
potential of the chalcone moiety may be exploited and some new ways could be suggested for
obtaining therapeutically active useful compounds.
Plan of Work
Early July Planning
July - August Literature Review
1-10 Sept Acquiring and chemicals
10-30 Sept Designing of Scheme
October- Synthesis and Evaluation
November
Thank YOU