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Review
. 2022 Jul 31;27(15):4901.
doi: 10.3390/molecules27154901.

Thiocoumarins: From the Synthesis to the Biological Applications

Maria J Matos  1   2 , Lourdes Santana  1 , Eugenio Uriarte  1   3 , Fernanda Borges  2
Affiliations
Review

Thiocoumarins: From the Synthesis to the Biological Applications

Maria J Matos et al. Molecules. .

Abstract

Coumarin is a privilege scaffold in medicinal chemistry. Coumarin derivatives are still an emerging class of highly potent pharmaceutical drugs, best known in the field of antimicrobials and anticoagulants. Thiocoumarins are a particular class of coumarins in which one or two of the oxygen atoms are replaced by a sulfur. They are chemically subdivided in three groups: Thiocoumarins, 2-thioxocoumarins, and dithiocoumarins. This review emphasizes the rationale behind the synthesis and biological applications of the most relevant publications related to this family of compounds. Particular attention has been given to their potential as drug candidates, with particular emphasis in the last 5 years. This article is based on the most relevant information collected from multiple electronic databases, including SciFinder, Pubmed, Espacenet, and Mendeley.

Keywords: 2-thioxocoumarins; biological applications; dithiocoumarins; synthesis; thiocoumarins.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Coumarin and its bioisosteres: Thiocoumarin, 2-thioxocoumarin, and dithiocoumarin.
Figure 2
Figure 2
Alternative method of cyclocondensation of thiocoumarins.
Figure 3
Figure 3
(A) Synthesis of thiocoumarins via traditional Lewis acid formation. (B) A straightforward organocatalytic synthesis of 4-aroylcoumarins. (C) Michael reactions at position 3 of the scaffold. (D) α-Regioselective Heck coupling of tosylates.
Figure 4
Figure 4
Conversion of thiocoumarins to dithiocoumarins.
Figure 5
Figure 5
Synthesis of 4-hydroxydithiocoumarins starting from 2’-chloroacetophenones.
Figure 6
Figure 6
Thio[3+2] cyclization reaction of 4-hydroxydithiocoumarins and trans-β-nitrostyrenes.
See this image and copyright information in PMC

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