Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2021 Dec 22:2021:2804521.
doi: 10.1155/2021/2804521. eCollection 2021.

Styrylchromones: Biological Activities and Structure-Activity Relationship

Mariana Lucas  1 , Marisa Freitas  1 , Artur M S Silva  2 , Eduarda Fernandes  1 , Daniela Ribeiro  1   3
Affiliations
Review

Styrylchromones: Biological Activities and Structure-Activity Relationship

Mariana Lucas et al. Oxid Med Cell Longev. .

Retraction in

Abstract

Styrylchromones (SC) are a group of oxygen-containing heterocyclic compounds, which are characterized by the attachment of a styryl group to the chromone core. SC can be found in nature or can be chemically synthesized in the laboratory. As their presence in nature is scarce, the synthetic origin is the most common. Two types of SC are known: 2-styrylchromones and 3-styrylchromones. However, 2-styrylchromones are the most common, being more commonly found in nature and which chemical synthesis is more commonly described. A wide variety of SC has been described in the literature, with different substituents in different positions, the majority of which are distributed on the A- and/or B-rings. Over the years, several biological activities have been attributed to SC. This work presents a comprehensive review of the biological activities attributed to SC and their structure-activity relationship, based on a published literature search, since 1989. The following biological activities are thoroughly revised and discussed in this review: antioxidant, antiallergic, antiviral, antibacterial, antifungal, anti-inflammatory, and antitumoral, affinity and selectivity for A3 adenosine receptors, neuroprotective, and α-glucosidase inhibition. In general, SC are composed by a promising scaffold with great potential for the development of new drugs.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structure and numbering of the chromone core [1].
Figure 2
Figure 2
Chemical structures of 2-SC (1) and 3-SC (2) and numbering system to be adopted throughout this review [3].
Figure 3
Figure 3
Biological activities described for 2-SC and 3-SC.
Figure 4
Figure 4
Chemical structures of 2-SC 1, 5, 11, and 13–19 [22, 24].
Figure 5
Figure 5
Chemical structures of 2-SC 17–20 [25].
Figure 6
Figure 6
Chemical structures of 2-SC 1, 5, 11, and 13–21 [26, 27].
Figure 7
Figure 7
Chemical structures of 2-SC 22–24 [28].
Figure 8
Figure 8
Chemical structures of 2-SC 25–27 [29].
Figure 9
Figure 9
Chemical structures of 2-SC 28–32 [30].
Figure 10
Figure 10
Chemical structures of 2-SC 3 and 33 [32].
Figure 11
Figure 11
Structural characteristics that seem to favour the 2-SC antioxidant activity.
Figure 12
Figure 12
Chemical structure of 3-SC 12 [13].
Figure 13
Figure 13
Chemical structures of 3-SC 34–50 [33].
Figure 14
Figure 14
Structural characteristics that seem to favour the 3-SC antioxidant activity.
Figure 15
Figure 15
Structural characteristics that seem to favour the 2-SC antiallergic activity.
Figure 16
Figure 16
Chemical structures of 2-SC 1, 21, and 56–61 [37].
Figure 17
Figure 17
Chemical structures of 2-SC 62–77 [38].
Figure 18
Figure 18
Chemical structures of 2-SC 78–80 [39].
Figure 19
Figure 19
Chemical structures of 2-SC 1, 5, 21, 56–58, 62, 70, and 81–83 [40].
Figure 20
Figure 20
Chemical structure of 2-SC 11 [12].
Figure 21
Figure 21
Structural characteristics that seem to favour the 2-SC antiviral activity against serotypes 1B and 14 of human rhinovirus (HRV) and murine norovirus (MNV).
Figure 22
Figure 22
Chemical structures of 3-SC 34–39 and 42–50 [43].
Figure 23
Figure 23
Chemical structures of 3-SC 2, 41, 84, and 85 [44].
Figure 24
Figure 24
Structural characteristics that seem to favour the 3-SC antiviral activity against serotype 1B of human rhinovirus (HRV).
Figure 25
Figure 25
Chemical structures of 2-SC 58, 78, and 86–93 [46].
Figure 26
Figure 26
Chemical structures of 2-SC 94–101 [47].
Figure 27
Figure 27
Chemical structures of 2-SC 1, 13, 56, 58, and 102 [48].
Figure 28
Figure 28
Chemical structures of 2-SC 28–32 [30].
Figure 29
Figure 29
Structural characteristics that seem to favour the 2-SC antibacterial activity.
Figure 30
Figure 30
Chemical structures of 2-SC 94–101 [47].
Figure 31
Figure 31
Chemical structures of 2-SC 1, 13, 56, 58, and 102 [48].
Figure 32
Figure 32
Chemical structures of 2-SC 28–32 [30].
Figure 33
Figure 33
Structural characteristics that seem to favour the 2-SC antifungal activity.
Figure 34
Figure 34
Chemical structures of 2-SC 3 and 33 [52].
Figure 35
Figure 35
Chemical structures of 2-SC 1, 5, 11, and 13–21 [54, 59].
Figure 36
Figure 36
Structural characteristics that seem to favour the 2-SC anti-inflammatory activity.
Figure 37
Figure 37
Chemical structures of 2-SC 3 and 4 [6, 7].
Figure 38
Figure 38
Chemical structures of 2-SC 1, 57, 58, 92, 93, and 103 [64].
Figure 39
Figure 39
Chemical structures of 2-SC 1, 30, 56, 58, 88, 92, and 104–115 [66].
Figure 40
Figure 40
Chemical structures of 2-SC 116–131 [67].
Figure 41
Figure 41
Chemical structures of 2-SC 1, 56, 58, 59, 92, 93, 103, 104, 125, and 132–147 [68].
Figure 42
Figure 42
Chemical structures of 2-SC 7–11 [10].
Figure 43
Figure 43
Chemical structures of 2-SC 148–151 [69].
Figure 44
Figure 44
Chemical structures of 2-SC 152–154 [70].
Figure 45
Figure 45
Chemical structures of 2-SC 155–163 [73].
Figure 46
Figure 46
Chemical structure of 2-SC 164 [76].
Figure 47
Figure 47
Structural characteristics that seem to favour the 2-SC antitumoral activity.
Figure 48
Figure 48
Chemical structures of 3-SC 34–39 and 42–50 [5, 43].
Figure 49
Figure 49
Chemical structures of 3-SC 2, 40, 41, and 165–175 [78].
Figure 50
Figure 50
Structural characteristics that seem to favour the 3-SC antitumoral activity.
See this image and copyright information in PMC

References

    1. Gaspar A., Matos M. J., Garrido J., Uriarte E., Borges F. Chromone: a valid scaffold in medicinal chemistry. Chemical Reviews . 2014;114(9):4960–4992. doi: 10.1021/cr400265z. - DOI - PubMed
    1. Keri R. S., Budagumpi S., Pai R. K., Balakrishna R. G. Chromones as a privileged scaffold in drug discovery: a review. European Journal of Medicinal Chemistry . 2014;78:340–374. doi: 10.1016/j.ejmech.2014.03.047. - DOI - PubMed
    1. Santos C. M. M., Silva A. M. S. An overview of 2-styrylchromones: natural occurrence, synthesis, reactivity and biological properties. European Journal of Organic Chemistry . 2017;2017(22):3115–3133. doi: 10.1002/ejoc.201700003. - DOI
    1. Gomes A., Freitas M., Fernandes E., Lima J. L. F. C. Biological activities of 2-styrylchromones. Mini-Reviews in Medicinal Chemistry . 2010;10(1):1–7. doi: 10.2174/138955710791112550. - DOI - PubMed
    1. Sakagami H., Shimada C., Kanda Y., et al. Effects of 3-styrylchromones on metabolic profiles and cell death in oral squamous cell carcinoma cells. Toxicology Reports . 2015;2:1281–1290. doi: 10.1016/j.toxrep.2015.09.009. - DOI - PMC - PubMed