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Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides.

ABSTRACT: : A series of sixteen ring-substituted N-arylcinnamamides was prepared and characterized. Primary in vitro screening of all the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium tuberculosis H37Ra, Fusarium avenaceum, and Bipolaris sorokiniana. Several of the tested compounds showed antistaphylococcal, antitubercular, and antifungal activities comparable with or higher than those of ampicillin, isoniazid, and benomyl. (2E)-N-[3,5-bis(trifluoromethyl)phenyl]-3-phenylprop-2-enamide and (2E)-3-phenyl-N-[3-(trifluoromethyl)phenyl]prop-2-enamide showed the highest activities (MICs = 22.27 and 27.47 µM, respectively) against all four staphylococcal strains and against M.tuberculosis. These compounds showed an activity against biofilm formation of S.aureus ATCC 29213 in concentrations close to MICs and an ability to increase the activity of clinically used antibiotics with different mechanisms of action (vancomycin, ciprofloxacin, and tetracycline). In time-kill studies, a decrease of CFU/mL of >99% after 8 h from the beginning of incubation was observed. (2E)-N-(3,5-Dichlorophenyl)- and (2E)-N-(3,4-dichlorophenyl)-3-phenylprop-2-enamide had a MIC = 27.38 µM against M. tuberculosis, while a significant decrease (22.65%) of mycobacterial cell metabolism determined by the MTT assay was observed for the 3,5-dichlorophenyl derivative. (2E)-N-(3-Fluorophenyl)- and (2E)-N-(3-methylphenyl)-3-phenylprop-2-enamide exhibited MICs = 16.58 and 33.71 µM, respectively, against B. sorokiniana. The screening of the cytotoxicity of the most effective antimicrobial compounds was performed using THP-1 cells, and these chosen compounds did not shown any significant lethal effect. The compounds were also evaluated for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. (2E)-N-(3,5-dichlorophenyl)-3-phenylprop-2-enamide (IC50 = 5.1 µM) was the most active PET inhibitor. Compounds with fungicide potency did not show any in vivo toxicity against Nicotiana tabacum var. Samsun. The structure?activity relationships are discussed.

SUBMITTER: Pospisilova S

PROVIDER: S-EPMC6121455 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides.

Pospisilova Sarka S Kos Jiri J Michnova Hana H Kapustikova Iva I Strharsky Tomas T Oravec Michal M Moricz Agnes M AM Bakonyi Jozsef J Kauerova Tereza T Kollar Peter P Cizek Alois A Jampilek Josef J

International journal of molecular sciences 20180807 8

: A series of sixteen ring-substituted N-arylcinnamamides was prepared and characterized. Primary in vitro screening of all the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium tuberculosis H37Ra, Fusarium avenaceum, and Bipolaris sorokiniana. Several of the tested compounds showed antistaphylococcal, antitubercular, and antifungal activities comparable with or higher t ...[more]

PMID: 30087309

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Project description:Herein, we report novel Co(II) and V(IV) complexes synthesized from an (E)-2-(((2-((2-hydroxyethyl)amino)quinolin-3-yl)methylene)amino)ethan-1-ol ligand (L), cobalt(II) chloride hexahydrate, and vanadyl(IV) sulfate in methanolic solutions. The ligand and the complexes were characterized by 1H NMR spectroscopy,13C NMR spectroscopy, UV-visible spectroscopy, fluorescence spectroscopy, FT-IR spectroscopy, powder X-ray diffraction (PXRD), scanning electron microscopy-energy dispersive X-ray spectroscopy (SEM-EDX), mass spectroscopy (MS), thermal analysis, and molar conductance. The FT-IR spectral data showed that the ligand adopted a tridentate fashion when binding with the metal ions via the nitrogen atoms of the imine (C=N) and amine (N-H), and the oxygen atom of the hydroxyl group (O-H). The PXRD and SEM results indicated that the complexes are amorphous in nature. The density functional theory (DFT) calculated absorption and IR spectra agree very well with the corresponding experimental results. The antibacterial activities of the free ligand and its complexes were evaluated using a paper disk diffusion method. The complexes have better percent activitiy index than the free ligand. The cobalt complex exhibited a more recognizable antibacterial activity than the vanadium complex, specifically against Pseudomonas aeruginosa with a mean inhibition zone of 18.62 ± 0.19 mm, when compared with the positive control, ciprofloxacin, with a mean inhibition zone of 22.98 ± 0.08 mm at the same concentration. Furthermore, the antioxidant activities of the free ligand and its metal complexes were also determined in vitro using 2,2-diphenyl-1-picrylhydrazyl. The ligand exhibited less in vitro antioxidant activity than its transition metal complexes, in which the cobalt complex has a better antioxidant activity with half-inhibitory concentrations (IC50 of 16.01 μg/mL) than the ligand and the vanadium complex. Quantum molecular descriptors from the DFT calculations further support the experimental results. Molecular docking analysis also shed more light on the biological activities of the novel cobalt and vanadium complexes.

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Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides.

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Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides.

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