New series of fused pyrazolopyridines: Synthesis, molecular modeling, antimicrobial, antiquorum-sensing and antitumor activities

El‐Gohary, Nadia S.; Hawas, Samia S.; Gabr, Moustafa T.; Shaaban, Mona I.; El‐Ashmawy, Mahmoud B.

doi:10.1016/j.bioorg.2019.103109

Cited by 16 publications

(6 citation statements)

References 59 publications

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“…According to the previous literature, not all pyrazolopyridine derivatives can interact with DNA (El-Gohary and Shaaban, 2018; El-Gohary et al, 2019;Suntharalingam et al, 2010). In addition, etazolate may possess antioxidant and neuroprotective properties as shown using animal models (Alzoubi et al, 2018;Alzoubi et al, 2017;Jindal et al, 2015Jindal et al, , 2017.…”

Section: Discussionmentioning

confidence: 99%

“…Etazolate is a neuroprotective agent that showed promising results in the treatment of Alzheimer's disease, depression, anxiety, and memory impairments (Alzoubi et al, 2018;Ankur et al, 2013;Drott et al, 2010;Jindal et al, 2015). Etazolate is a pyrazolopyridine derivative, and previous studies showed that some pyrazolopyridine-derived compounds could interact with DNA (El-Gohary and Shaaban, 2018;El-Gohary et al, 2019;Suntharalingam et al, 2010). In addition, some pyrazolopyridine derivatives showed antitumor and antiproliferative activity and could block the progression of the cell cycle (Baviskar et al, 2013;Gavriil et al, 2016).…”

Section: Discussionmentioning

confidence: 99%

“…However, studies that examine the genotoxicity and cytotoxicity of etazolate to human cells are needed. Previous studies showed that some pyrazolopyridine derivatives might have DNA-binding affinity (El-Gohary and Shaaban, 2018;El-Gohary et al, 2019;Suntharalingam et al, 2010). In addition, some pyrazolopyridine derivatives showed antitumor and antiproliferative activity and could interfere with cell cycle progression (Baviskar et al, 2013;Butu et al, 2014Butu et al, , 2015Gavriil et al, 2016;Rodino et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

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Assessment of the genotoxicity and cytotoxicity of etazolate in cultured human lymphocytes

Halabi¹,

Khabour²,

Alzoubi³

2022

j app pharm sci

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Etazolate is a pyrazolopyridine compound that exhibits a range of pharmacological mechanisms, including inhibition of phosphodiesterase-4 activity and modulation of the γ-aminobutyric acid (GABA) signaling pathway. Etazolate has shown promising results in treating depression, traumatic brain injury, and Alzheimer's disease in animal models and clinical trials. However, limited information is available regarding its genotoxicity and cytotoxicity to human cells. Therefore, the current study aims at testing the effect of etazolate on the genetic material using two genotoxicity assays. In addition, the study aims to evaluate the effect of etazolate on the mitotic index (MI) of cultured human lymphocytes. Different concentrations of etazolate (0.01, 1, 10, and 50 µM) were used. Genotoxicity was assessed using the chromosomal aberrations (CAs) assay, and oxidative DNA damage was assessed using the 8-hydroxy-2deoxyguanosine (8-OHdG) assay, while cytotoxicity was assessed using the MI assay. Treatment of cultured human lymphocytes with etazolate did not induce CAs at all concentrations examined (p > 0.05). In addition, the normal level of 8-OHdG detected in the control group was not affected by etazolate treatment (p > 0.05). Furthermore, no effect was observed for etazolate on the MI (p > 0.05). In conclusion, current results indicate that etazolate is neither genotoxic nor cytotoxic to cultured human lymphocytes using the indicated assays at the examined concentrations.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Assessment of the genotoxicity and cytotoxicity of etazolate in cultured human lymphocytes

Halabi¹,

Khabour²,

Alzoubi³

2022

j app pharm sci

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“…However, according to our best knowledge, none of those compounds exhibited comparable antistaphylococcal activity (MIC values below 1 µg/mL) [33][34][35][36]. Moreover, the results presented by other authors did not indicate similar selectivity of antimicrobial properties (high activity against Gram-positive bacteria and no activity against both Gram-negative bacteria and human pathogenic yeasts) [33][34][35]. In some cases, it is difficult to compare results, because different method of determination of antimicrobial activity (disc diffusion) was used by the authors [33,34].…”

Section: Chemistrymentioning

confidence: 95%

Anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-triones as a New Class of Antistaphylococcal Agents: Synthesis and Biological Evaluation

et al. 2019

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The development and spread of resistance of human pathogenic bacteria to the action of commonly used antibacterial drugs is one of the key problems in modern medicine. One of the especially dangerous and easily developing antibiotic resistant bacterial species is Staphylococcus aureus. Anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-triones 22–38 have been developed as novel effective antistaphylococcal agents. These compounds have been obtained by sequential conversion of 1-amino-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid (1) and 1-amino-4-bromo-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid (2) into the corresponding amides 5–21, followed by subsequent endo-cyclization under the influence of sodium nitrite in acetic acid. Evaluation of the antimicrobial activity of the synthesized compounds against selected species of Gram-positive and Gram-negative bacteria as well as pathogenic yeasts of the Candida genus has been carried out by the serial dilution method. It has been established that anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-triones exhibit selective antibacterial activity against Gram-positive bacteria. Eight, six and seven, out of seventeen compounds tested, effectively inhibited the growth of S. aureus ATCC 25923, S. aureus ATCC 29213 and S. epidermidis ATCC12228, respectively, at a concentration equal to 1 µg/mL or lower. The high antistaphylococcal potential of the most active compounds has been also confirmed against clinical isolates of S. aureus, including the MRSA strains. However, bacteria of the Staphylococcus genus have demonstrated apparent resistance to the novel compounds when grown as a biofilm. None of the four selected compounds 3234 and 36 at a concentration of 64 µg/mL (128 or 256 × MIC—against planktonic cells) has caused any decrease in the metabolic activity of the staphylococcal cells forming the biofilm. The kinetic time–kill assay revealed some important differences in the activity of these substances. Compound 33 is bacteriostatic, while the other three demonstrate bactericidal activity.

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“…Pyrazolo[4′,3′:5,6]pyrido[2,3- d ]pyrimidines analogs were reported to have diverse pharmacological activities, including as anticonvulsants, antiproliferative agents, anti-inflammatories and analgesic agents, antibacterial, antifungal, antimicrobial and antitumor activities [ 28 , 29 , 30 , 31 ]. Further, pyrazolo[4′,3′:5,6]pyrido[3,2- e ][1,2,4]triazolo[4,3- a ]pyrimidinone analogs were reported as antimicrobial agents [ 32 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Molecular Docking Study of Novel Pyrimidine Derivatives against COVID-19

et al. 2023

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A novel series of pyrido[2,3-d]pyrimidines; pyrido[3,2-e][1,3,4]triazolo; and tetrazolo[1,5-c]pyrimidines were synthesized via different chemical transformations starting from pyrazolo[3,4-b]pyridin-6-yl)-N,N-dimethylcarbamimidic chloride 3b (prepared from the reaction of o-aminonitrile 1b and phosogen iminiumchloride). The structures of the newly synthesized compounds were elucidated based on spectroscopic data and elemental analyses. Designated compounds are subjected for molecular docking by using Auto Dock Vina software in order to evaluate the antiviral potency for the synthesized compounds against SARS-CoV-2 (2019-nCoV) main protease M pro. The antiviral activity against SARS-CoV-2 showed that tested compounds 7c, 7d, and 7e had the most promising antiviral activity with lower IC50 values compared to Lopinavir, “the commonly used protease inhibitor”. Both in silico and in vitro results are in agreement.

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New series of fused pyrazolopyridines: Synthesis, molecular modeling, antimicrobial, antiquorum-sensing and antitumor activities

Cited by 16 publications

References 59 publications

Assessment of the genotoxicity and cytotoxicity of etazolate in cultured human lymphocytes

Assessment of the genotoxicity and cytotoxicity of etazolate in cultured human lymphocytes

Anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-triones as a New Class of Antistaphylococcal Agents: Synthesis and Biological Evaluation

Synthesis and Molecular Docking Study of Novel Pyrimidine Derivatives against COVID-19

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