Synthesis and pharmacological assessment of diversely substituted pyrazolo[3,4-b]quinoline, and benzo[b]pyrazolo[4,3-g][1,8]naphthyridine derivatives

Silva, Daniel da; Chioua, Mourad; Samadi, Abdelouahid; Carreiras, M. Carmo; Jimeno, M. Luísa; Mendes, Eduarda; Rı́os, Cristóbal de los; Romero, Alejandro; Villarroya, Mércedes; López, Manuela G.; Marco‐Contelles, José

doi:10.1016/j.ejmech.2011.05.068

Cited by 51 publications

(29 citation statements)

References 63 publications

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“…A new series of pyrazolotacrine as acetylcholinesterase (AChE) inhibitors ( Figure 41 ) were reported by Silva et al The results showed that compound 434 was the most potent inhibitor of AChE, which inhibited the aforementioned enzyme with an IC 50 value of 0.069 µM [ 331 ]. Khoobi et al synthesized a new tetracyclic tacrine analogs containing pyrano[2,3- c ]pyrazole and evaluated for inhibition of acetylcholinesterase (AChE).…”

Section: Pharmacological Activitiesmentioning

confidence: 99%

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

et al. 2018

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Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. The presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antipsychotic CDPPB, the anti-obesity drug rimonabant, difenamizole, an analgesic, betazole, a H2-receptor agonist and the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Owing to this diversity in the biological field, this nucleus has attracted the attention of many researchers to study its skeleton chemically and biologically. This review highlights the different synthesis methods and the pharmacological properties of pyrazole derivatives. Studies on the synthesis and biological activity of pyrazole derivatives developed by many scientists around the globe are reported.

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Section: Pharmacological Activitiesmentioning

confidence: 99%

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

et al. 2018

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“…Diverse pyrazole derivatives (Compounds 76 – 81 ; Silva et al, ; Silva, Samadi, Chioua, Carreiras, & Marco‐Contelles, ) and (phenoxyalkoxybenzylidenemalononitriles (Compounds 81 and 82 ; Silva et al, ) were previously synthesized and their AChE inhibitory activities reported. Here we describe their inhibitory activities in rat mitochondria (rMAO A and rMAO B; Table S2).…”

Section: Resultsmentioning

confidence: 99%

Synthesis, biological evaluation, and molecular modeling of nitrile‐containing compounds: Exploring multiple activities as anti‐Alzheimer agents

Silva

Mendes

Summers

et al. 2019

Drug Development Research

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Based on the monoamine oxidase (MAO) inhibition properties of aminoheterocycles with a carbonitrile group we have carried out a systematic exploration to discover new classes of carbonitriles endowed with dual MAO and AChE inhibitory activities, and Aβ anti‐aggregating properties. Eighty‐three nitrile‐containing compounds, 13 of which are new, were synthesized and evaluated. in vitro screening revealed that 31, a new compound, presented the best lead for trifunctional inhibition against MAO A (0.34 μM), MAO B (0.26 μM), and AChE (52 μM), while 32 exhibited a lead for selective MAO A (0.12 μM) inhibition coupled to AChE (48 μM) inhibition. Computational analysis revealed that the malononitrile group can find an advantageous position with the aromatic cleft and FAD of MAO A or MAO B. However, the total binding energy can be handicapped by an internal penalty caused by twisting of the ligand molecule and subsequent disruption of the conjugation (32 in MAO B compared to the conjugated 31). Conjugation is also important for AChE as well as the hydrophilic character of malononitrile that allows this group to be in close contact with the aqueous environment as seen for 83. Although the effect of 31 and 32 against Aβ1–42, was very weak, the effect of 63 and 65, and of the new compound 75, indicated that these compounds were able to disaggregate Aβ1–42 fibrils. The most effective was 63, a (phenylhydrazinylidene)propanedinitrile derivative that also inhibited MAO A (1.65 μM), making it a potential lead for Alzheimer's disease application.

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“…Its mechanism of action involved a slight elevation in the cytosolic concentration of Ca 2þ in Fura-2-loaded bovine chromaffin cells. In addition, exposure of bovine chromaffin cells to neuroprotective concentrations of this compound [135]. 1,8-Naphthyridine analogs, synthesized as hybrids of tacrine and 1,4-dihydropyridines, were reported by Le on and coworkers [136] as multitarget drugs for Alzheimer and other neuronal vascular diseases.…”

Section: Applications In Neurological Disordersmentioning

confidence: 99%

“…Pyrazolo[3,4‐ b ]quinoline and benzo[ b ]pyrazolo[4,3‐ g ][1,8]naphthyridine ( 73 ) derivatives have been reported as potential inhibitors of Electrophorus electricus acetylcholinesterase (EeAChE) and serum horse butyrylcholinesterase (eqBuChE) . 1,8‐Naphthyridine analogs, synthesized as hybrids of tacrine and 1,4‐dihydropyridines, were reported by León and coworkers as multitarget drugs for Alzheimer and other neuronal vascular diseases.…”

Section: Biological Properties Of 18‐naphthyridine Derivativesmentioning

confidence: 99%

1,8‐Naphthyridine Derivatives: A Review of Multiple Biological Activities

Madaan

Verma

Kumar

et al. 2015

Archiv der Pharmazie

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The 1,8-naphthyridine group of compounds have gained special attention of researchers on account of their demonstrating a variety of interesting biological activities. A wide range of biological properties establishes them as potent scaffolds in therapeutic and medicinal research. The broad spectrum of activities primarily includes antimicrobial, antiviral, anticancer, anti-inflammatory, and analgesic activities. 1,8-Naphthyridine derivatives have also exhibited potential applications in neurological disorders such as Alzheimer's disease, multiple sclerosis, and depression. In addition, these synthetic derivatives have been found to possess activities such as anti-osteoporotic (α(v)β(3) antagonists), anti-allergic, antimalarial, gastric antisecretory, bronchodilator, anticonvulsant, anti-hypertensive, platelet aggregation inhibition, anti-oxidant, EGFR inhibition, protein kinase inhibition, ionotropic agent, β-3 antagonist, MDR modulator, adenosine receptor agonist, adrenoceptor antagonist, and pesticide activities. In spite of the widespread application of the 1,8-naphythyridine scaffolds, only a limited number of review articles are available till date. In this review, we attempt to compile and discuss the key data available in the literature for the multiple biological activities of 1,8-naphthyridine derivatives, in a chronological manner. This review compilation (with 199 references) may be helpful in understanding the diverse biological properties of 1,8-naphthyridines and provide insights into their mechanism of action. This may direct future research in the synthesis of new derivatives and exploring this scaffold for other possible biological activities.

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Synthesis and pharmacological assessment of diversely substituted pyrazolo[3,4-b]quinoline, and benzo[b]pyrazolo[4,3-g][1,8]naphthyridine derivatives

Cited by 51 publications

References 63 publications

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

Synthesis, biological evaluation, and molecular modeling of nitrile‐containing compounds: Exploring multiple activities as anti‐Alzheimer agents

1,8‐Naphthyridine Derivatives: A Review of Multiple Biological Activities

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