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Antimicrobial Activity of 4-Chlorocinnamic Acid Derivatives
Rayanne H N Silva1, Ana C M Andrade2, Diego F Nóbrega2
1Laboratory of Pharmaceutical Chemistry, Department of Pharmaceutical Sciences, Federal University of Paraíba, Cidade Universitária, João Pessoa, Paraíba 58051-900, Brazil.
Biomed Research International
|June 11, 2019
Summary
New 4-chlorocinnamic acid esters show potent antimicrobial and antifungal activity. Certain esters, like methoxyethyl and perillyl 4-chlorocinnamate, are particularly effective against fungi, potentially inhibiting the 14α-demethylase enzyme.
Area of Science:
- Medicinal Chemistry
- Organic Synthesis
- Antimicrobial Research
Background:
- Microbial resistance in fungi and bacteria is a significant global health concern.
- Cinnamic acid esters possess diverse pharmacological properties, including antimicrobial effects.
Purpose of the Study:
- To synthesize and evaluate a series of 4-chlorocinnamic acid esters for antimicrobial and antifungal activities.
- To investigate the potential of these esters as inhibitors of the fungal enzyme 14α-demethylase.
Main Methods:
- Synthesis of 4-chlorocinnamic acid esters via Fischer esterification, alkyl/aryl halide esterification, Mitsunobu, and Steglich reactions.
- Antimicrobial testing against *Candida* species, *Pseudomonas aeruginosa*, and *Staphylococcus aureus*.
- Molecular docking simulations targeting the 14α-demethylase enzyme.
Main Results:
- Twelve 4-chlorocinnamic acid esters were synthesized, including three novel compounds.
- Methyl 4-chlorocinnamate (1) showed activity against *S. aureus*.
- Methoxyethyl 4-chlorocinnamate (4) and perillyl 4-chlorocinnamate (11) exhibited potent antifungal activity (MICs of 0.13 and 0.024 μmol/mL).
- Molecular docking indicated good affinity of the esters to the 14α-demethylase active site.
Conclusions:
- The synthesized 4-chlorocinnamic acid esters demonstrate significant antimicrobial and antifungal potential.
- Methoxyethyl and perillyl 4-chlorocinnamate are promising candidates for further development as antifungal agents.
- The esters may act by inhibiting the 14α-demethylase enzyme, crucial for fungal growth.
- Structural features like short alkyl chains with heteroatoms or perillyl moieties enhance antifungal efficacy.
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