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. 2022 Jan 14;12(1):131.
doi: 10.3390/biom12010131.

Synthesis and Biological Evaluation of Benzo[ b]thiophene Acylhydrazones as Antimicrobial Agents against Multidrug-Resistant Staphylococcus aureus

Thibaut Barbier  1 , Alexia Barbry  2   3 , Jérémy Magand  1 , Cédric Badiou  3 , Floriane Davy  3 , Anne Baudouin  4 , Yves Queneau  1 , Oana Dumitrescu  2   3 , Gérard Lina  2   3 , Laurent Soulère  1
Affiliations

Synthesis and Biological Evaluation of Benzo[ b]thiophene Acylhydrazones as Antimicrobial Agents against Multidrug-Resistant Staphylococcus aureus

Thibaut Barbier et al. Biomolecules. .

Abstract

The benzo[b]thiophene nucleus and the acylhydrazone functional group were combined to prepare three new series of compounds for screening against Staphylococcus aureus. The reaction of substituted benzo[b]thiophene-2-carboxylic hydrazide and various aromatic or heteroaromatic aldehydes led to a collection of 26 final products with extensive structural diversification on the aromatic ring and on position 6 of the benzo[b]thiophene nucleus. The screening lead to the identification of eight hits, including (E)-6-chloro-N'-(pyridin-2-ylmethylene)benzo[b]thiophene-2-carbohydrazide (II.b), a non-cytotoxic derivative showing a minimal inhibitory concentration of 4 µg/mL on three S. aureus strains, among which were a reference classical strain and two clinically isolated strains resistant to methicillin and daptomycin, respectively.

Keywords: MRSA; Staphylococcus aureus; acylhydrazone; antibacterial; benzothiophene.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
General structure of set I derivatives.
Scheme 1
Scheme 1
Synthesis of set I derivatives.
Figure 2
Figure 2
1H NMR spectra of I.a at different temperatures.
Figure 2
Figure 2
1H NMR spectra of I.a at different temperatures.
Scheme 2
Scheme 2
Synthesis of compound I.p.
Figure 3
Figure 3
General structure of set II derivatives.
Scheme 3
Scheme 3
Synthesis of set II and III derivatives.
Scheme 4
Scheme 4
Synthesis of III.d.
Scheme 5
Scheme 5
Synthesis of III.e.
Figure 4
Figure 4
Effect of II.b on the growth of A549 cells.
See this image and copyright information in PMC

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