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 Jul 19;14(7):692.
doi: 10.3390/ph14070692.

Thiophene-Based Compounds with Potential Anti-Inflammatory Activity

Ryldene Marques Duarte da Cruz  1 , Francisco Jaime Bezerra Mendonça-Junior  1   2 , Natália Barbosa de Mélo  2 , Luciana Scotti  1 , Rodrigo Santos Aquino de Araújo  2 , Reinaldo Nóbrega de Almeida  1 , Ricardo Olímpio de Moura  2
Affiliations
Review

Thiophene-Based Compounds with Potential Anti-Inflammatory Activity

Ryldene Marques Duarte da Cruz et al. Pharmaceuticals (Basel). .

Abstract

Rheumatoid arthritis, arthrosis and gout, among other chronic inflammatory diseases are public health problems and represent major therapeutic challenges. Non-steroidal anti-inflammatory drugs (NSAIDs) are the most prescribed clinical treatments, despite their severe side effects and their exclusive action in improving symptoms, without effectively promoting the cure. However, recent advances in the fields of pharmacology, medicinal chemistry, and chemoinformatics have provided valuable information and opportunities for development of new anti-inflammatory drug candidates. For drug design and discovery, thiophene derivatives are privileged structures. Thiophene-based compounds, like the commercial drugs Tinoridine and Tiaprofenic acid, are known for their anti-inflammatory properties. The present review provides an update on the role of thiophene-based derivatives in inflammation. Studies on mechanisms of action, interactions with receptors (especially against cyclooxygenase (COX) and lipoxygenase (LOX)), and structure-activity relationships are also presented and discussed. The results demonstrate the importance of thiophene-based compounds as privileged structures for the design and discovery of novel anti-inflammatory agents. The studies reveal important structural characteristics. The presence of carboxylic acids, esters, amines, and amides, as well as methyl and methoxy groups, has been frequently described, and highlights the importance of these groups for anti-inflammatory activity and biological target recognition, especially for inhibition of COX and LOX enzymes.

Keywords: anti-inflammatory drugs; cyclooxygenase; inflammation; lipoxygenase; molecular docking; thiophene.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of market anti-inflammatory drugs containing a thiophene moiety (Tinoridine, Tiaprofenic acid, Tenidap and Zileuton.).
Figure 2
Figure 2
Simplified diagram of COX-1, COX-2 and LOX enzymes activation and beginning of the inflammatory process.
Figure 3
Figure 3
Chemical structures of thiophene-based compounds active against COX and LOX enzymes.
Figure 4
Figure 4
Chemical structures of thiophene-based compounds, which modulate gene expression and/or inflammatory cytokines.
Figure 5
Figure 5
Chemical structures of thiophene-based compounds with anti-inflammatory properties in classic models of inflammation.
Figure 6
Figure 6
Chemical structures of thiophene-based compounds with anti-inflammatory properties in in silico studies.
Figure 7
Figure 7
Representative figure of the general mechanisms of action of the thiophene-based compounds presented in this review.
See this image and copyright information in PMC

References

    1. Yeung Y.T., Aziz F., Guerrero-Castilla A., Arguelles S. Signaling Pathways in Inflammation and Anti-inflammatory Therapies. Curr. Pharm. Des. 2018;24:1449–1484. doi: 10.2174/1381612824666180327165604. - DOI - PubMed
    1. Mack M. Inflammation and fibrosis. Matrix Biol. 2018;68–69:106–121. doi: 10.1016/j.matbio.2017.11.010. - DOI - PubMed
    1. Muszynska B., Grzywacz-Kisielewskaa A., Kala K., Gdula-Argasinska J. Anti-inflammatory properties of edible mushrooms: A review. Food Chem. 2018;243:373–381. doi: 10.1016/j.foodchem.2017.09.149. - DOI - PubMed
    1. De Oliveira Pedrosa Rolim M., De Almeida A.R., Da Rocha Pitta M.G., De Melo Rêgo M.J.B., Quintans-Júnior L.J., De Souza Siqueira Quintans J., Heimfarth L., Scotti L., Scotti M.T., Da Cruz R.M.D., et al. Design, synthesis and pharmacological evaluation of CVIB, a codrug of carvacrol and ibuprofen as a novel anti-inflammatory agent. Int. Immunopharmacol. 2019;76:105856. doi: 10.1016/j.intimp.2019.105856. - DOI - PubMed
    1. Lahsasni S., Al-Hemyari D.A.M., Ghabbour H.A., Mabkhoot Y.N., Aleanizy F.S., Alothman A.A., Almarhoon Z.M. Synthesis, Characterization, and Antibacterial and Anti-Inflammatory Activities of New Pyrimidine and Thiophene Derivatives. J. Chem. 2018;2018:8536063. doi: 10.1155/2018/8536063. - DOI

LinkOut - more resources