Design, synthesis, anticonvulsant and analgesic studies of new pyrazole analogues: a Knoevenagel reaction approach

a b s t r a c tThe pyrazolone structural motif is a critical element of drugs aimed at different biological end-points. Medicinal chemistry researches have synthesized drug-like pyrazolone candidates with several medicinal features including antimicrobial, antitumor, CNS (central nervous system) effect, anti-inflammatory activities and so on. Meanwhile, SAR (Structure-Activity Relationship) investigations have drawn attentions among medicinal chemists, along with a plenty of analogues have been derived for multiple targets. In this review, we comprehensively summarize the biological activity and SAR for pyrazolone analogues, wishing to give an overall retrospect and prospect on the pyrazolone derivatives.

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“…Viveka et al [68] prepared pyrazolone analogues 99 and 100 ( Fig. 9) with favorable anticonvulsant activities.…”

Section: Anticonvulsant Agentsmentioning

confidence: 99%

Pyrazolone structural motif in medicinal chemistry: Retrospect and prospect

Zhao

Dai

et al. 2020

European Journal of Medicinal Chemistry

149

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“…The IR spectra (400-4000 cm −1 ) were recorded on the Nicolet iS10 FT-IR spectrometer using KBr Wafer technique. 1 H-NMR spectrum was recorded with a Varian Gemini spectrometer at 400 MHz with TMS as the internal standard and chemical shifts were reported on a δ scale (ppm) using CDCl 3 or DMSO-d 6 as solvents, while the coupling constants (J values) are given in Hz. Elemental analyses (C, H, N, and S) were carried out at the Microanalytical Data Centre at the Faculty of Science, Cairo University, Egypt.…”

Section: General Informationmentioning

confidence: 99%

“…The pyrazole nucleus is a ubiquitous feature of a pharmacophoric scaffold, which represents a class of heterocyclic compounds with a wide range of biological applications. Many of them are widely used as potent analgesic, antiarrhythmic and anticonvulsant [1], antidiabetic [2], anticancer [3], anti-inflammatory [4,5], anti-conceptive and antipyretic [6], muscle relaxing [7], antifungal [8,9], antibacterial activities [8], insecticidal [10], herbicidal [11], anti HIV, antagonist of OPL1, BACE inhibitors for the treatment of Alzheimer's disease, hepatitis C virus, and hypoxia inducible factor [12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and in-vitro antioxidant and antitumor evaluation of novel pyrazole-based heterocycles

Ismail

El‐Sayed

2018

J IRAN CHEM SOC

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Hydrazide-hydrazone, namely, N′-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)-2-cyanoacetohydrazide 3, was utilized as a key starting material for the construction of a variety of novel heterocyclic moieties. The newly synthesized compounds were characterized by elemental analyses and spectral data (IR, 1 H-NMR, and mass spectra). Some of the newly synthesized compounds were screened for their antitumor and antioxidant activities. The results showed clearly that compounds 6, 11, 13, 22, and 29 displayed promising in-vitro antitumor activity against two cell lines (HepG2 and MCF-7). Among these compounds, compounds 13 and 29 exhibited the highest activity as antitumor agents. On the other hand, compounds 13, 22, and 29 exhibited the highest inhibitory antioxidant activity using ABTS method. While, in case of erythrocytes hemolysis, compounds 4, 13, and 29 proved to exhibit potent antioxidative activity as vitamin C. Meanwhile, compounds 6, 11, 16, 21, and 22 showed a remarkable promising activity. In light of the highest potency of our novel compounds in targeting both antitumor and antioxidant activities, compounds 13 and 29 warrant persistent preclinical development as antitumor and antioxidant agents.

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“…Owing to increase of resistant cooperated hosts, the incidence of universal bacterial infections has increased persistently . Also, the side effects of some antibiotics are more difficult to tackle than the disease itself.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biological Evaluation, and Molecular Docking Studies of Some N‐thiazolyl Hydrazones and Indenopyrazolones

Mor

Sindhu

Nagoria

et al. 2019

Journal of Heterocyclic Chem

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Two new series of N‐thiazolyl hydrazones (3a–h) and indenopyrazolones (4a–h) were synthesized by the reaction of various 2‐acyl‐(1H)‐indene‐1,3(2H)‐diones, thiosemicarbazide, and phenacyl bromide/substituted phenacyl bromides. The in vitro antimicrobial activity of these synthesized compounds was assayed against four bacteria, namely, Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa, and two fungi, namely, Candida albicans and Aspergillus niger, by employing serial dilution method. Ciprofloxacin and fluconazole were used as antibacterial and antifungal reference drugs, respectively. Results of antimicrobial assay showed that the tested compounds have broad range of activity. The compounds 3h and 4a against C. albicans displayed more potency than fluconazole whereas 3b and 3c against B. subtilis showed activity comparable with ciprofloxacin. The synthesized indenopyrazolones (4a–h) were evaluated for their in vitro antioxidant activity by 2,2‐diphenyl‐1‐picrylhydrazyl radical scavenging assay using ascorbic acid as reference. Compound 4b exhibited the highest 2,2‐diphenyl‐1‐picrylhydrazyl radical scavenging with IC50 value 33.14 μg/mL. The observed results of antimicrobial activity were supported by molecular docking study performed to understand the binding interaction of hydrazones (3a–h) and indenopyrazolones (4a–h) with lanosterol 14α‐demethylase.

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Design, synthesis, anticonvulsant and analgesic studies of new pyrazole analogues: a Knoevenagel reaction approach

Abstract: Compounds1a,4aand7a(76.58, 79.76 and 78 94% protection) shows potent anticonvulsant activity compounds1b,5a,5b,7aand7bshowed good analgesic property.

Cited by 38 publications

References 40 publications

Pyrazolone structural motif in medicinal chemistry: Retrospect and prospect

Pyrazolone structural motif in medicinal chemistry: Retrospect and prospect

Synthesis and in-vitro antioxidant and antitumor evaluation of novel pyrazole-based heterocycles

Synthesis, Biological Evaluation, and Molecular Docking Studies of Some N‐thiazolyl Hydrazones and Indenopyrazolones

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