Novel 4-(3-phenylpropionamido), 4-(2-phenoxyacetamido) and 4-(cinnamamido) substituted benzamides bearing the pyrazole or indazole nucleus: synthesis, biological evaluation and mechanism of action

Raffa, Demetrio; D’Anneo, Antonella; Plescia, Fulvio; Daidone, Giuseppe; Lauricella, Marianna; Maggio, Benedetta

doi:10.1016/j.bioorg.2018.10.055

Cited by 8 publications

(6 citation statements)

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“…Pyrazole derivatives as an inducer of apoptosis in cancer cells have already been reported. Demetrio Raffa et al, (2019) studied a series of Pyrazole derivatives on a human lung carcinoma cell line and they revealed the apoptotic cell death by activating TRAIL death receptors followed by caspase-8 activation (extrinsic pathway) or changes in p53 activation (intrinsic pathway). Another study (Czarnomysy et al, 2018) investigated the complexation of Pyrazole derivatives with platinum to enhance their therapeutic effect.…”

Section: Discussionmentioning

confidence: 99%

Pyrazole Derivatives Induce Apoptosis via ROS Generation in the Triple Negative Breast Cancer Cells, MDA-MB-468

Ashourpour

Hosseini

Amini

et al. 2021

Asian Pac J Cancer Prev

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Breast cancer is one of the most common cancers among women and is a major reason for cancer death worldwide (Rakha et al., 2010). According to the literature, the incidence of female breast cancer in various countries was accounted for up to 3.2 million new cases per year by 2050 (Tao et al., 2015). Basically, breast cancer is a heterogeneous complex of diseases which involve a broad spectrum of subtypes (Yersal and Barutca, 2014).

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Section: Discussionmentioning

confidence: 99%

Pyrazole Derivatives Induce Apoptosis via ROS Generation in the Triple Negative Breast Cancer Cells, MDA-MB-468

Ashourpour

Hosseini

Amini

et al. 2021

Asian Pac J Cancer Prev

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“…For the colony formation assay, a single cell suspension (200 cells/well) was plated into each well of a 6-well plate and incubated at 37 °C for 2 weeks. The colonies were fixed and stained with a dye solution containing crystal violet as reported by Raffa et al [71]. All assays were replicated three times.…”

Section: Methodsmentioning

confidence: 99%

Ethanol-Mediated Stress Promotes Autophagic Survival and Aggressiveness of Colon Cancer Cells via Activation of Nrf2/HO-1 Pathway

Cernigliaro

D’Anneo

Carlisi

et al. 2019

Cancers

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Epidemiological studies suggest that chronic alcohol consumption is a lifestyle risk factor strongly associated with colorectal cancer development and progression. The aim of the present study was to examine the effect of ethanol (EtOH) on survival and progression of three different colon cancer cell lines (HCT116, HT29, and Caco-2). Our data showed that EtOH induces oxidative and endoplasmic reticulum (ER) stress, as demonstrated by reactive oxygen species (ROS) and ER stress markers Grp78, ATF6, PERK and, CHOP increase. Moreover, EtOH triggers an autophagic response which is accompanied by the upregulation of beclin, LC3-II, ATG7, and p62 proteins. The addition of the antioxidant N-acetylcysteine significantly prevents autophagy, suggesting that autophagy is triggered by oxidative stress as a prosurvival response. EtOH treatment also upregulates the antioxidant enzymes SOD, catalase, and heme oxygenase (HO-1) and promotes the nuclear translocation of both Nrf2 and HO-1. Interestingly, EtOH also upregulates the levels of matrix metalloproteases (MMP2 and MMP9) and VEGF. Nrf2 silencing or preventing HO-1 nuclear translocation by the protease inhibitor E64d abrogates the EtOH-induced increase in the antioxidant enzyme levels as well as the migration markers. Taken together, our results suggest that EtOH mediates both the activation of Nrf2 and HO-1 to sustain colon cancer cell survival, thus leading to the acquisition of a more aggressive phenotype.

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“…The mixture was left under hydrogenation in a Parr apparatus at 50 psi for 24 h. The suspension was ltered, and the ltrate was concentrated to a small volume. affording a compound which was identical in all respect (mp, mixed mp, Rf, IR, 1H-NMR) with an authentic specimen of ethyl 5-(4-aminobenzamido)-1-methyl-1H-pyrazole-4-carboxylate 25a[23] and ethyl 5-(4-aminobenzamido)-1-phenyl-1H-pyrazole-4-carboxylate 25e[22]. Compound 31 was isolated as white crystalline product.5-(4-aminobenzamido)-1-methyl-1H-pyrazole-4-carboxylic acid (31): yields: 68%; mp 248 − 50°C.…”

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confidence: 90%

“…General procedure for preparation of compounds 20a,e[21,22].A solution of ethyl 1-R-5-amino-1H-pyrazole-4-carboxylate 19a,e (0.01 mole) in acetonitrile (50 mL) was heated under re ux with the 4-nitrobenzoyl chloride 18 (0.01 mole) for 7h. The solid which separated was collected then recrystallized from ethanol to give compounds 20a,e which was identical in all respect (mp, mixed mp, Rf, IR, 1H-NMR) with an authentic specimen of ethyl 1-methyl-5-(4-nitrobenzamido)-1Hpyrazole-4-carboxylate 20a[21] and ethyl 5-(4-nitrobenzamido)-1-phenyl-1H-pyrazole-4-carboxylate 20e[22] 4…”

mentioning

confidence: 99%

“….1.4. General procedure for preparation of ethyl compounds 25a,e[23,22] and 31.To a solution of ethyl 1-R-5-(4-nitrobenzamido)-1H-pyrazole-4-carboxylate 20a,e (0.013 moles) or 1methyl-5-(4-nitrobenzamido)-1H-pyrazole-4-carboxylic acid 31 (0.017 moles) in warm ethanol (200 mL) 300 mg of 10% Pd-C as catalyst was added. The mixture was left under hydrogenation in a Parr apparatus at 50 psi for 24 h. The suspension was ltered, and the ltrate was concentrated to a small volume.…”

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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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Novel 4-(3-phenylpropionamido), 4-(2-phenoxyacetamido) and 4-(cinnamamido) substituted benzamides bearing the pyrazole or indazole nucleus: synthesis, biological evaluation and mechanism of action

Cited by 8 publications

References 37 publications

Pyrazole Derivatives Induce Apoptosis via ROS Generation in the Triple Negative Breast Cancer Cells, MDA-MB-468

Pyrazole Derivatives Induce Apoptosis via ROS Generation in the Triple Negative Breast Cancer Cells, MDA-MB-468

Ethanol-Mediated Stress Promotes Autophagic Survival and Aggressiveness of Colon Cancer Cells via Activation of Nrf2/HO-1 Pathway

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.

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