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Review
. 2022 Oct 11;15(10):1250.
doi: 10.3390/ph15101250.

Chalcone: A Promising Bioactive Scaffold in Medicinal Chemistry

Gayathri Rajendran  1   2 , Deepu Bhanu  1   2 , Baladhandapani Aruchamy  1   2 , Prasanna Ramani  1   2 , Nanjan Pandurangan  3 , Kondapa Naidu Bobba  4 , Eun Jung Oh  5 , Ho Yun Chung  5   6 , Prakash Gangadaran  6   7 , Byeong-Cheol Ahn  6   7
Affiliations
Review

Chalcone: A Promising Bioactive Scaffold in Medicinal Chemistry

Gayathri Rajendran et al. Pharmaceuticals (Basel). .

Abstract

Chalcones are a class of privileged scaffolds with high medicinal significance due to the presence of an α,β-unsaturated ketone functionality. Numerous functional modifications of chalcones have been reported, along with their pharmacological behavior. The present review aims to summarize the structures from natural sources, synthesis methods, biological characteristics against infectious and non-infectious diseases, and uses of chalcones over the past decade, and their structure-activity relationship studies are detailed in depth. This critical review provides guidelines for the future design and synthesis of various chalcones. In addition, this could be highly supportive for medicinal chemists to develop more promising candidates for various infectious and non-infectious diseases.

Keywords: Claisen–Schmidt condensation; chalcones; infectious diseases; natural sources; non-infectious diseases; structure–activity relationship.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structure of chalcone and its bioactivities (e.g., anticancer, antibacterial, antiviral, anti-tubercular).
Figure 2
Figure 2
Naturally occurring chalcones: (A) hydroxylated and methoxylated chalcones; (B) chromene-based chalcones; (C) prenylated chalcones; (D) quinone-, cinnamoyl-, and dihydro-bearing chalcones.
Figure 2
Figure 2
Naturally occurring chalcones: (A) hydroxylated and methoxylated chalcones; (B) chromene-based chalcones; (C) prenylated chalcones; (D) quinone-, cinnamoyl-, and dihydro-bearing chalcones.
Scheme 1
Scheme 1
Chalcone synthesis via Claisen–Schmidt condensation.
Scheme 2
Scheme 2
Various methods to synthesize chalcones.
Scheme 3
Scheme 3
Synthesis of chalcones by aerobic oxidative cross-coupling reaction.
Scheme 4
Scheme 4
Synthesis of chalcones by cross-dehydrogenative coupling.
Scheme 5
Scheme 5
Synthesis of substituted chalcones through Julia–Kocienski olefination.
Scheme 6
Scheme 6
Synthesis of cis-chalcones by reductive (3+2) annulation.
Scheme 7
Scheme 7
One-pot synthesis of chalcones.
Scheme 8
Scheme 8
Synthesis of chalcones via photo-Fries rearrangement.
Scheme 9
Scheme 9
Wittig reaction for the synthesis of chalcones.
Figure 3
Figure 3
Structures of some chalcones showing anti-tubercular activity.
Figure 4
Figure 4
Chalcones with antiviral activity.
Figure 5
Figure 5
Structures of chalcones with antimalarial activity.
Figure 6
Figure 6
Chalcones with anti-bacterial activity: (A) homocyclic chalcones; (B) heterocyclic chalcones.
Figure 7
Figure 7
Chalcones for Alzheimer’s disease.
Figure 8
Figure 8
Homocyclic chalcones with anti-breast-cancer activity [170,171,172,173,174,175,176,177,178,179,180,181,182,183].
Figure 9
Figure 9
Heterocyclic chalcones with anti-breast-cancer activity [23,184,185,186,187,188,189,190,191,192,193,194,195,196,197,198,199,200,201,202,203,204,205,206,207,208].
Figure 9
Figure 9
Heterocyclic chalcones with anti-breast-cancer activity [23,184,185,186,187,188,189,190,191,192,193,194,195,196,197,198,199,200,201,202,203,204,205,206,207,208].
Figure 10
Figure 10
(A,B) Chalcones with anti-lung-cancer activity and their IC50 values [187,193,200,209,210,211,212,213,214,215,216,217].
Figure 10
Figure 10
(A,B) Chalcones with anti-lung-cancer activity and their IC50 values [187,193,200,209,210,211,212,213,214,215,216,217].
Figure 11
Figure 11
Structures of chalcones with antidiabetic activity.
Figure 12
Figure 12
Chalcones showing anti-Parkinson’s activity.
Figure 13
Figure 13
Flowchart depicting the structure–activity relationships of natural and synthetic chalcones.
See this image and copyright information in PMC

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