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. 2025 Jan;17(2):183-193.
doi: 10.1080/17568919.2024.2444867. Epub 2024 Dec 26.

Novel coumarin linked pyrazoles, thiazoles, and thiadiazoles: synthetic strategies and in vitro antimicrobial investigation

Salwa A Elsharabasy  1 , Mariam T Sayed  1 , Anhar Abdel-Aziem  1
Affiliations

Novel coumarin linked pyrazoles, thiazoles, and thiadiazoles: synthetic strategies and in vitro antimicrobial investigation

Salwa A Elsharabasy et al. Future Med Chem. 2025 Jan.

Abstract

Aim: Emerging resistance among pathogens necessitates the development of novel antimicrobial agents. As a result, we aimed to synthesize new coumarins and study their antimicrobial activity with the hope of obtaining effective drugs.

Method: A series of coumarins were synthesized, characterized, and assessed for antimicrobial activity using broth microdilution and agar diffusion methods against Gram-positive (Bacillus pumilis, Streptococcus faecalis), Gram-negative (Escherichia coli, Enterobacter cloacae) bacteria, and fungi (Saccharomyces cerevisiae, Candida albicans).

Results: Pyrazoles 15 and 16 revealed promising activities against all bacterial strains with MIC values ranging from 1.95 to 15.6 µg/ml. Notably, pyrazole 15 with CF3 in 3-position of pyrazole ring demonstrated higher ability to inhibit Streptococcus faecalis strain with MIC value equal to penicillin G (3.91 µg/ml). It also exhibited the best bactericidal potency against Escherichia coli with MBC value of 15.6 µg/ml while, pyrazole 16 recorded the same MBC value against Enterobacter cloacae. Pyrazole 15 demonstrated the strongest antifungal activity against both fungal strains with MIC and MFC values of 15.6, 7.81, 62.5, and 31.3 µg/ml against Saccharomyces cerevisiae and Candida albicans, respectively.

Conclusion: These findings underscore the potential of coumarins, particularly compounds 15 and 16, as effective antimicrobial agents and provide critical insights into the design of bioactive molecules.

Keywords: 1,3-thiazoles, 1.3.4-thiadiazines; Coumarins; antimicrobial activity; pyrazoles.

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Conflict of interest statement

The authors have no relevant affiliations or financial involvement with any organization or entity with a financial interest in or financial conflict with the subject matter or materials discussed in the manuscript. This includes employment, consultancies, honoraria, stock ownership or options, expert testimony, grants or patents received or pending, or royalties.

Figures

Figure 1.
Figure 1.
Examples of medicinally important pyrazole and coumarin medicines.
Figure 2.
Figure 2.
Rationale design of synthesized coumarin hybrids as antimicrobial agents.
Figure 3.
Figure 3.
Reactions of 3-acetyl-6-bromo-2H-chromen-2-one.
Figure 4.
Figure 4.
Reactions of 6-bromo-3-(2-bromo-acetyl)-chromen-2-one.
Figure 5.
Figure 5.
The most active tested compounds recording the lowest MICs, MBCs and MFCs.
See this image and copyright information in PMC

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