Trypanocidal activity of new 1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine derivatives: Synthesis, in vitro and in vivo studies

Ribeiro, Joana L.S.; Soares, Júlio C.A.V.; Portapilla, Gisele Bulhões; Providello, Maiara Voltarelli; Lima, Camilo Henrique da Silva; Muri, Estela M.F.; Albuquerque, Sérgio de; Dias, Luiza R.S.

doi:10.1016/j.bmc.2020.115855

Cited by 15 publications

(4 citation statements)

References 40 publications

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“…Taking into account the broadly understood concept of antimicrobial effect, 1,3,4- In 2021, Ribeiro et al developed a series of 1,3,4-oxadiazole bearing pyrazolo [3,4-b]pyridine scaffold derivatives and tested their antitrypanocidal activity. The most potent compound in vitro was 63 (Figure 21), whose activity against amastigotes forms of T. cruzi (IC 50 = 1.11 µM) was significantly higher than that of the reference drug benznidazole (IC 50 = 3.98 µM) [98].…”

Section: Antiviral Activity Of 134-oxadiazole Derivativesmentioning

confidence: 99%

“…In 2021, Ribeiro et al developed a series of 1,3,4-oxadiazole bearing pyrazolo [3,4b]pyridine scaffold derivatives and tested their antitrypanocidal activity. The most potent compound in vitro was 63 (Figure 21), whose activity against amastigotes forms of T. cruzi (IC50 = 1.11 µM) was significantly higher than that of the reference drug benznidazole (IC50 = 3.98 µM) [98]. Furthermore, researchers from Brazil led by Chaves and Espinosa (2017, 2020) received a series of gold(I) phosphine complexes with 2-mercapto-1,3,4-oxadiazoles and checked their activity against Leishmania spp.…”

Section: Antitrypanocidal Activity Of 134-oxadiazole Derivativesmentioning

confidence: 99%

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Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives

Glomb

Świątek

2021

IJMS

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The worldwide development of antimicrobial resistance forces scientists to search for new compounds to which microbes would be sensitive. Many new structures contain the 1,3,4-oxadiazole ring, which have shown various antimicrobial activity, e.g., antibacterial, antitubercular, antifungal, antiprotozoal and antiviral. In many publications, the activity of new compounds exceeds the activity of already known antibiotics and other antimicrobial agents, so their potential as new drugs is very promising. The review of active antimicrobial 1,3,4-oxadiazole derivatives is based on the literature from 2015 to 2021.

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Section: Antiviral Activity Of 134-oxadiazole Derivativesmentioning

confidence: 99%

Section: Antitrypanocidal Activity Of 134-oxadiazole Derivativesmentioning

confidence: 99%

Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives

Glomb

Świątek

2021

IJMS

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“…Research results showed that compounds containing 2,3-dihydro-1,3,4-oxadiazole groups had good active structures in the body. Compound 17 showed potential trypanocidal activity against Trypanosoma cruzi amastigotes with IC 50 value of 1.11 ± 0.29 μM compared with the standard drug Benznidazole (IC 50 = 3.98 ± 0.28 μM) 25 .…”

Section: Oxadiazolementioning

confidence: 99%

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Wang

Sun

Jia

et al. 2022

Journal of Enzyme Inhibition and Medicinal Chemistry

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Oxadiazole is a five-membered heterocyclic compound containing two nitrogen atoms and one oxygen atom. The 1,3,4-oxadiazole and 1,2,4-oxadiazole have favourable physical, chemical, and pharmacokinetic properties, which significantly increase their pharmacological activity via hydrogen bond interactions with biomacromolecules. In recent years, oxadiazole has been demonstrated to be the biologically active unit in a number of compounds. Oxadiazole derivatives exhibit antibacterial, anti-inflammatory, anti-tuberculous, anti-fungal, anti-diabetic and anticancer activities. In this paper, we report a series of compounds containing oxadiazole rings that have been published in the last three years only (2020–2022) as there was no report or their activities described in any article in 2019, which will be useful to scientists in research fields of organic synthesis, medicinal chemistry, and pharmacology.

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“…The benzopyrazole derivative GW2974 [ 15 ] shares a similar scaffold to pyrazolo[3,4- b ]pyridine compounds, which we have extensively studied in our labs [ 16 , 17 , 18 ], including their analogs [ 19 ]. Interestingly, when these moieties are rationally assembled in a single scaffold, such as pyrazolo[3,4- b ]pyridines, they have shown antitumoral [ 20 ], antibacterial/microbial [ 21 ], trypanocidal [ 22 ], antidepressant, anxiolytic [ 23 ], antiviral [ 24 ], and anti-inflammatory [ 25 ] activities, making these structural moieties an invaluable source of new bioactive molecules of interest in the medicinal chemistry field.…”

Section: Introductionmentioning

confidence: 99%

5-(Indol-2-yl)pyrazolo[3,4-b]pyridines as a New Family of TASK-3 Channel Blockers: A Pharmacophore-Based Regioselective Synthesis

et al. 2021

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TASK channels belong to the two-pore-domain potassium (K2P) channels subfamily. These channels modulate cellular excitability, input resistance, and response to synaptic stimulation. TASK-channel inhibition led to membrane depolarization. TASK-3 is expressed in different cancer cell types and neurons. Thus, the discovery of novel TASK-3 inhibitors makes these bioactive compounds very appealing to explore new cancer and neurological therapies. TASK-3 channel blockers are very limited to date, and only a few heterofused compounds have been reported in the literature. In this article, we combined a pharmacophore hypothesis with molecular docking to address for the first time the rational design, synthesis, and evaluation of 5-(indol-2-yl)pyrazolo[3,4-b]pyridines as a novel family of human TASK-3 channel blockers. Representative compounds of the synthesized library were assessed against TASK-3 using Fluorometric imaging plate reader—Membrane Potential assay (FMP). Inhibitory properties were validated using two-electrode voltage-clamp (TEVC) methods. We identified one active hit compound (MM-3b) with our systematic pipeline, exhibiting an IC50 ≈ 30 μM. Molecular docking models suggest that compound MM-3b binds to TASK-3 at the bottom of the selectivity filter in the central cavity, similar to other described TASK-3 blockers such as A1899 and PK-THPP. Our in silico and experimental studies provide a new tool to predict and design novel TASK-3 channel blockers.

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Trypanocidal activity of new 1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine derivatives: Synthesis, in vitro and in vivo studies

Cited by 15 publications

References 40 publications

Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives

Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

5-(Indol-2-yl)pyrazolo[3,4-b]pyridines as a New Family of TASK-3 Channel Blockers: A Pharmacophore-Based Regioselective Synthesis

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