Synthetic Cinnamides and Cinnamates: Antimicrobial Activity, Mechanism of Action, and In Silico Study (original) (raw)
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SYNTHETIC CINNAMATES AS POTENTIAL ANTIMICROBIAL AGENTS
Chemical industry, 2014
This study deals with synthesis of methyl cinnamate, butyl cinnamate, and p-methoxy methyl cinnamate and testing of their in vitro antimicrobial activity. Antimicrobial activity was examined towards 29 microorganisms using microdilution method. It is shown that antimicrobial activity of methyl cinnamate and p-methoxy methyl cinnamate was better than that of butyl cinnamate. Sarcina lutea, Bacillus subtilis ATCC 6633, B. subtilis and B. subtilis IP 5832 (probiotic) were the most sensitive bacteria. It is established that p-methoxy methyl cinnamate can be a new, potential anti-Staphylococcus aureus agent with minimum inhibitory concentration of 62.5 μg/ml. Methyl cinnamate and p-methoxy methyl cinnamate inhibited the growth of Aspergillus restrictus, A. flavus and A. fumigatus in the concentration range from 62.5 μg/ml to 250 μg/ml.
European journal of …, 2004
A series of esters (I a-k ), substituted derivatives (II a-d ) and amides (III a-q ) of cinnamic acid were synthesized and evaluated as antibacterial and antifungal agents. All the derivatives belonging to the series I, II and III showed antimicrobial activity comparable to the standard. Compounds I f and II c proved to be the most effective compounds. Quantitative structure-activity relationship (QSAR) investigation with multiple linear regression analysis was applied to find a correlation between different calculated physicochemical parameters of the compounds and biological activity. The quantitative models relating the structural features of cinnamic acid derivatives I a-k , II a-d and III a-q and their antimicrobial activity showed that Gram negative Escherichia coli and Candida albicans (fungus) were the most sensitive microorganisms.
Synthesis of Cinnamanilide Derivatives and Their Antioxidant and Antimicrobial Activity
Journal of Chemistry, 2015
The amide derivatives of cinnamic acid were synthesized and their antimicrobial and antioxidant activities were investigated. The investigation of antimicrobial potentials of the compounds demonstrated a strong activity against 21 bacterial strains comprising Gram-positive and Gram-negative bacteria. Compounds2a,2b, and3bshowed strong antimicrobial activity against all microorganisms with the pMIC value ranging from 2.45 to 3.68. Compounds2a,3a, and3bdemonstrated strong antioxidant activity with % inhibition of the DPPH radical of 51% (±1.14), 41% (±1.01), and 50% (±1.23), respectively. These findings indicate that the amide derivatives of the cinnamic acid possess strong antibacterial and antioxidant activities.
International research journal of pharmacy, 2019
A series of 2-(benzamido)-N-(3-(4-(dimethylamino)phenyl)allylidene)-3-(substitutedphenyl)acrylohydrazides(3a-m) were synthesized by nucleophilic condensation of various substituted α-benzamido cinnamhydrazides(2a-m) with dimethylaminocinnamaldehyde in presence of ethanol and few drops of glacial acetic acid. The chemical structures of synthesized compounds were confirmed by means of IR, 1 H NMR, mass spectral and elemental analysis. Among the compounds evaluated, vanillinyl(3c) and 4-hydroxy-3,4-dimethoxy derivatives(3d) exhibited good antimicrobial activity against all the strains tested, which was comparable to that of standard drugs Ciprofloxacin and Fluconazole and 4-hydroxy-3,4-dimethoxyderivative(3d) showed good antioxidant activity towards all the four models. All the derivatives obey Lipinski rule of five and has good bioactive scores.
Molecules
Cinnamic acid is a plant metabolite with antimicrobial, anticancer, and antioxidant properties. Its synthetic derivatives are often more effective in vitro than parent compounds due to stronger biological activities. In our study, we synthesized ten new N–(4–chloro–2–mercapto–5–methylphenylsulfonyl)cinnamamide derivatives, containing two pharmacophore groups: cinnamic acid moiety and benzenesulfonamide. The antimicrobial activity of the obtained compounds was estimated using different types of Gram-positive and Gram-negative bacteria, fungus species of Candida albicans, as well as clinical strains. The compounds were evaluated on biofilm formation and biofilm formed by Staphylococcus clinical strains (methicillin–resistance S. aureus MRSA and methicillin–resistance coagulase–negative Staphylococcus MRCNS). Furthermore, blood bacteriostatic activity test was performed using S. aureus and S. epidermidis. In cytotoxic study, we performed in vitro hemolysis assay on domestic sheep perip...
Synthesis and Biological Evaluation of Novel Cinnamic Acid-Based Antimicrobials
Pharmaceuticals, 2022
The main antimicrobial resistance (AMR) nosocomial strains (ESKAPE pathogens such as Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, and Enterobacter spp.) are the most widespread bacteria in cutaneous infections. In this work we report the synthesis, in silico skin permeability prediction, antimicrobial, antibiofilm, and wound healing properties of novel cinnamic acid-based antimicrobials (DM1–11) as novel antibacterial drugs for the treatment of ESKAPE-related skin infections. Antimicrobial and wound healing scratch assays were performed to evaluate the antibacterial properties of DM1–11. In silico skin permeability capabilities of DM1–11 were evaluated using Swiss-ADME online database. Cytotoxicity assays were performed on keratinocytes and fibroblasts. DM2, bearing a catechol group on the aromatic ring of the cinnamic portion of the molecule, possesses a significant antibacterial activity against S. aureus (MIC...
Structure−Antifungal Activity Relationship of Cinnamic Acid Derivatives
Journal of Agricultural and Food Chemistry, 2007
A structure-antifungal activity relationship (SAR) study of 22 related cinnamic acid derivatives was carried out. Attention was focused on the antifungal activities exhibited against Aspergillus flavus, Aspergillus terreus, and Aspergillus niger. (E)-3-(4-Methoxy-3-(3-methylbut-2-enyl)phenyl)acrylic acid (16) exhibited antifungal activity against A. niger, comparable to that of miconazole and a significant antifungal effect against A. flavus and A. terreus as well. A structure-activity relationship (SAR) study of related cinnamic acid derivatives has allowed a model to be proposed for the recognition of the minimal structural requirements for the antifungal effect in this series.
Natural cinnamic acids, synthetic derivatives and hybrids with antimicrobial activity
Molecules (Basel, Switzerland), 2014
Antimicrobial natural preparations involving cinnamon, storax and propolis have been long used topically for treating infections. Cinnamic acids and related molecules are partly responsible for the therapeutic effects observed in these preparations. Most of the cinnamic acids, their esters, amides, aldehydes and alcohols, show significant growth inhibition against one or several bacterial and fungal species. Of particular interest is the potent antitubercular activity observed for some of these cinnamic derivatives, which may be amenable as future drugs for treating tuberculosis. This review intends to summarize the literature data on the antimicrobial activity of the natural cinnamic acids and related derivatives. In addition, selected hybrids between cinnamic acids and biologically active scaffolds with antimicrobial activity were also included. A comprehensive literature search was performed collating the minimum inhibitory concentration (MIC) of each cinnamic acid or derivative against the reported microorganisms. The MIC data allows the relative comparison between series of molecules and the derivation of structure-activity relationships.
Total synthesis of (-)-2-methoxy-2-butenolide-3-cinnamate and its antimicrobial potentials
Natural Product Research, 2020
The first total synthesis of (-)-2-methoxy-2-butenolide-3-cinnamate (butenolide cinnamate) was achieved using commercially available starting material. The synthesized compound was found to have promising antibacterial activity against Gram-negative strains Escherichia coli(ATCC 8739), Salmonella typhimurium(ATCC 23564), and Pseudomonas aeruginosa(ATCC 19154) with minimum inhibitory concentration of 2.0µg/ml, 1.0µg/ml and 2.0µg/ml respectively. Notably, the compound was more potent against Gram-negative test strains than the Gram-positive test strains.
Biological Activities and ADMET-Related Properties of Novel Set of Cinnamanilides
Molecules, 2020
A series of nineteen novel ring-substituted N-arylcinnamanilides was synthesized and characterized. All investigated compounds were tested against Staphylococcus aureus as the reference strain, two clinical isolates of methicillin-resistant S. aureus (MRSA), and Mycobacterium tuberculosis. (2E)-N-[3-Fluoro-4-(trifluoromethyl)phenyl]-3-phenylprop-2-enamide showed even better activity (minimum inhibitory concentration (MIC) 25.9 and 12.9 µM) against MRSA isolates than the commonly used ampicillin (MIC 45.8 µM). The screening of the cell viability was performed using THP1-Blue™ NF-κB cells and, except for (2E)-N-(4-bromo-3-chlorophenyl)-3-phenylprop-2-enamide (IC50 6.5 µM), none of the discussed compounds showed any significant cytotoxic effect up to 20 μM. Moreover, all compounds were tested for their anti-inflammatory potential; several compounds attenuated the lipopolysaccharide-induced NF-κB activation and were more potent than the parental cinnamic acid. The lipophilicity values w...