Synthesis, antiproliferative activity and possible mechanism of action of novel 2-acetamidobenzamides bearing the 2-phenoxy functionality

Raffa, Demetrio; Maggio, Benedetta; Plescia, Fulvio; Cascioferro, Stella; Raimondi, Maria Valeria; Cancemi, Gabriella; D’Anneo, Antonella; Lauricella, Marianna; Cusimano, Maria Grazia; Bai, Ruoli; Hamel, Ernest; Daidone, Giuseppe

doi:10.1016/j.bmc.2015.08.027

Cited by 13 publications

(5 citation statements)

References 26 publications

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“…The development of compounds with desired physicochemical properties, pharmacokinetic, and pharmacodynamic profiles is an essential issue of medicinal chemistry, which can benefit from the support of in silico studies [ [2] , [3] , [4] ]. Incessant optimization of lead compounds to obtain new drug-like molecules represents the pivotal challenge of drug discovery [ [5] , [6] , [7] , [8] ]. The use of heterocycles as bioisosteres for a variety of functional groups is a strategic path to obtain clinically safer drugs, thereby increasing affinity and potency towards their respective targets [ 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

Bioactive pyrrole-based compounds with target selectivity

Petri

Spanò

Spatola

et al. 2020

European Journal of Medicinal Chemistry

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177

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The discovery of novel synthetic compounds with drug-like properties is an ongoing challenge in medicinal chemistry. Natural products have inspired the synthesis of compounds for pharmaceutical application, most of which are based on N -heterocyclic motifs. Among these, the pyrrole ring is one of the most explored heterocycles in drug discovery programs for several therapeutic areas, confirmed by the high number of pyrrole-based drugs reaching the market. In the present review, we focused on pyrrole and its hetero-fused derivatives with anticancer, antimicrobial, and antiviral activities, reported in the literature between 2015 and 2019, for which a specific target was identified, being responsible for their biological activity. It emerges that the powerful pharmaceutical and pharmacological features provided by the pyrrole nucleus as pharmacophore unit of many drugs are still recognized by medicinal chemists.

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Section: Introductionmentioning

confidence: 99%

Bioactive pyrrole-based compounds with target selectivity

Petri

Spanò

Spatola

et al. 2020

European Journal of Medicinal Chemistry

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177

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“…For these experiments, MDA-MB231 cells were plated in 96-well plate (8×10 3 /well) in the presence of different concentrations of the compounds. After 48 h cell viability was determined by a colorimetric assay incubating the cells with 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), as reported [10,11]. MTT is yellow tetrazolium salt that can be reduced to purple formazan by mitochondrial enzymes of living cells.…”

Section: Cell Viability Assaymentioning

confidence: 99%

“…On the basis of our previously research [8][9][10][11] and considering the biological activity of 4-acetamido-Nmethylbenzamides and the antibio lm activity described by us for pyrazole-4-carboxamides [18], previously synthesized benzamides 8-11 (Fig. 2) have been modi ed according to Fig.…”

Section: Introductionmentioning

confidence: 99%

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A very promising antibiofilm activity against Candida albicans from an in vitro screening for antimicrobial, antibiofilm and antiproliferative activity of new synthesized 4-cinnamamido- and 2-phenoxyacedamido-1H-pyrazol-5-yl)benzamides.

Plescia

Catania

D’Anneo

et al. 2022

Preprint

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Several new synthesized 4-cinnamamido- and 2-phenoxyacedamido-1H-pyrazol-5-yl)benzamides were obtained by two multi step different synthetic routes in order to maximize their yield. The new derivatives were screened to determinate the antiproliferative, antimicrobial and antibiofilm activity. The biological results showed how, respect to the antiproliferative and antimicrobial activities, the compounds showed a low to missing activity. Different are the results obtained with respect to the antibiofilm activity, especially towards Candida albicans. Most of the synthesized compounds showed a good percentage inhibition of biofilm formation ranging from 60 to 73% with a Biofilm Inhibition Concentration 50% (BIC50) from 0.13 to 0.01 µM. Among the synthesized the ethyl 5-(4-(2-(4-chlorophenoxy)acetamido)benzamido)-1-methyl-1H-pyrazole-4-carboxylate (27c) resulted the most active with a BIC50 of 0.01 µM. According to the result obtained, such compound could be considered a lead subject of further studies to obtain novel and more effective antibiofilm agents against C. albicans infections.

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“…Amide compounds were widely used in pharmaceutical and agrochemical fields due to their wide range of biological activity. In pharmaceutical chemistry, some amides showed potent antibacterial activities and antiproliferative against human cancer cell lines including the drug-resistant cancer cells [1,2,3]. The other amides not only induce a significant decrease of antibiotic resistance in Gram-negative bacteria [4], but also exhibit antimicrobial activity against Staphylococcus aureus and Bacillus subtilis [5,6,7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Fungicidal Activities of (Z/E)-3,7-Dimethyl-2,6-octadienamide and Its 6,7-Epoxy Analogues

et al. 2015

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Abstract:In order to find new lead compounds with high fungicidal activity, (Z/E)-3,7-dimethyl-2,6-octadienoic acids were synthesized via selective two-step oxidation using the commercially available geraniol/nerol as raw materials. Twenty-eight different (Z/E)-3,7-dimethyl-2,6-octadienamide derivatives were prepared by reactions of (Z/E)-carboxylic acid with various aromatic and aliphatic amines, followed by oxidation of peroxyacetic acid to afford their 6,7-epoxy analogues. All of the compounds were characterized by HR-ESI-MS and 1 H-NMR spectral data. The preliminary bioassays showed that some of these compounds exhibited good fungicidal activities against Rhizoctonia solani (R. solani) at a concentration of 50 µg/mL. For example, 5C, 5I and 6b had 94.0%, 93.4% and 91.5% inhibition rates against R. solani, respectively. Compound 5f displayed EC 50 values of 4.3 and 9.7 µM against Fusahum graminearum and R. Solani, respectively.

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Synthesis, antiproliferative activity and possible mechanism of action of novel 2-acetamidobenzamides bearing the 2-phenoxy functionality

Cited by 13 publications

References 26 publications

Bioactive pyrrole-based compounds with target selectivity

Bioactive pyrrole-based compounds with target selectivity

A very promising antibiofilm activity against Candida albicans from an in vitro screening for antimicrobial, antibiofilm and antiproliferative activity of new synthesized 4-cinnamamido- and 2-phenoxyacedamido-1H-pyrazol-5-yl)benzamides.

Synthesis and Fungicidal Activities of (Z/E)-3,7-Dimethyl-2,6-octadienamide and Its 6,7-Epoxy Analogues

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