Facile sonochemical synthesis of novel pyrazolyne derivates at ambient conditions

Pacheco, Dency José; Prent-Peñaloza, Luis; Trilleras, Jorge; Quiroga, Jairo

doi:10.1016/j.ultsonch.2012.11.018

Cited by 18 publications

(7 citation statements)

References 33 publications

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“…Overall, the USI was the most effective method, and it surpassed methods A and B in terms of decreasing the reaction times while increasing yields parallel to obtaining regioselectively the 5-(indol-2-yl)pyrazolo[3,4- b ]pyridines MM-3a–i . These results could be explained by the physical phenomenon of acoustic cavitation, which has extensively provided more benefits in a variety of synthetic reactions [ 30 , 32 ]. Regardless of the synthetic method, we do not see a clear influence of the substitution pattern of the pyrazole ring on the obtained times and reaction yields ( Table 1 ).…”

Section: Resultsmentioning

confidence: 99%

“…To approach the pharmacophore-based regioselective synthesis of the 5-(indol-2yl)pyrazolo [3,4-b]pyridines MM-3a-i of interest, we synthesized the 2-(3,3-dimethylindolin-2-ylidene)malonaldehyde 1 [28,29] and a library of 5-aminopyrazoles 2a-i as building blocks (see Section 4.1). The cyclocondensation reaction between the dialdehyde 1 and 5aminopyrazole 2a did not progress under reflux conditions using ethanol as solvent or basic conditions using triethylamine, as reported for similar cyclocondensation reactions [30]. Then, we explored three additional synthetic protocols under acidic conditions: method A:…”

Section: Synthesis Of Designed Task-3 Blockersmentioning

confidence: 95%

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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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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Designed Task-3 Blockersmentioning

confidence: 95%

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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“…. In this work we present the preparation of 1‐aryl‐tetrahydro‐β‐carbolines under US‐assisted methodology in order to remark its advantages . Our interest in this target heterocycle is stimulated by their close structural relationship to molecules with antileishmanial and antitubercular activities .…”

Section: Methodsmentioning

confidence: 99%

Ultrasound Assisted Pictet–Spengler Synthesis of Tetrahydro‐β‐Carboline Derivatives

Muscia

Maria

Buldain

et al. 2015

Journal of Heterocyclic Chem

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The synthesis of twelve tetrahydro‐β‐carboline derivatives 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l prepared via the Pictet–Spengler reaction is described. The reaction of tryptamine and a variety of arylaldehydes were carried out under ultrasonic irradiation and trifluoracetic acid catalysis at room temperature. These tetrahydro‐β‐carbolines have been synthesized in higher yields and shorter reaction times compared to the conventional method. Moreover, the reaction proceeded successfully even employing arylaldehydes with electron‐donating or electron‐attracting substituents which did not react under conventional method.

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“…It was reported that different pyrazolines possess different activities such as anticancer [4], anti-inflammatory [5], antidepressant [6], antimalarial [7], antifungal [8], antibacterial [9], antioxidant [10], antitubercular [11], analgesic [12], and insecticidal [13] activities. The cyclocondensation reaction of chalcones with hydrazines is one of the most popular methods to synthesize pyrazoline derivatives [14].…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis, Cytotoxicity Evaluation and Molecular Docking Studyof <i>N</i>-Phenylpyrazoline Derivatives

2019

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The synthesis of N-phenylpyrazolines 1-5 was performed by the cyclocondensation of phenylhydrazine and appropriate chalcones that have been synthesized from our previous work. All of the compounds were elucidated for their structure using GC-MS, FTIR, 1H, and 13C-NMR spectrometers. Their anticancer activity was evaluated against breast cancer cell line (T47D) and colorectal cancer cell line (WiDr). Compound 4 (4-(3-(4-chlorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl)-2-methoxyphenol) was found to be the most potent compound with IC50 value of 13.11 µg/mL in T47D cell line and 3.29 µg/mL in WiDr cell line. Docking study was conducted to evaluate the interaction between all compounds and EGFR receptor on cancer cells. Among the tested compounds, compound 4 is the only compound that has interaction with MET769 residue through hydrogen bonding due to the presence of hydroxyl group on its structure. Our findings suggest that the synthesized N-phenylpyrazolines in this study have a promising anticancer activity.

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Facile sonochemical synthesis of novel pyrazolyne derivates at ambient conditions

Cited by 18 publications

References 33 publications

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

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

Ultrasound Assisted Pictet–Spengler Synthesis of Tetrahydro‐β‐Carboline Derivatives

Synthesis, Cytotoxicity Evaluation and Molecular Docking Studyof <i>N</i>-Phenylpyrazoline Derivatives

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