Multiple biological activities and molecular docking studies of newly synthesized 3-(pyridin-4-yl)-1H-pyrazole-5-carboxamide chalcone hybrids

Sribalan, Rajendran; Banuppriya, Govindharasu; Kirubavathi, Maruthan; Jayachitra, A.; Padmini, Vediappen

doi:10.1016/j.bmcl.2016.10.075

Cited by 43 publications

(11 citation statements)

References 37 publications

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“…Recently, the study of pyrazole as a pharmacophore for the development of potential antioxidants has led to the synthesis of several compounds containing pyrazole core in their structures. Among the reported synthetic pyrazoles: 3-(Pyridin-4-yl)-1H-pyrazole-5-carboxamide chalcones VII showed potent radical scavenging activity (RSA) against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical 28 , Moreover, in comparison with the standard ascorbic acid, 1,5-diarylpyrazoles VIII showed good DPPH RSA 29 . It was found that 3,5-diarylpyrazole IX has shown potent RSA as well.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, molecular modelling and biological evaluation of novel 3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives as potent antioxidants and 15-Lipoxygenase inhibitors

Ali

Awad

Said

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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Oxidative stress is one of the main causes of significant severe diseases. The discovery of new potent antioxidants with high efficiency and low toxicity is a great demand in the field of medicinal chemistry. Herein, we report the design, synthesis molecular modelling and biological evaluation of novel hybrids containing pyrazole, naphthalene and pyrazoline/isoxazoline moiety. Chalcones 2a-e were synthesized efficiently and were used as starting materials for synthesis of a variety of heterocycles. A novel series of pyrazoline 3a-e, phenylpyrazoline 4a-e, isoxazoline 5a-e and pyrazoline carbothioamide derivatives 6a-e were synthesized and screened for in vitro antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH), nitric oxide (NO) and superoxide radical scavenging assay as well as 15-lipoxygenase (15-LOX) inhibition activity. Compounds 3a, 4e, 5b, 5c, 6a, 6c, and 6e showed excellent radical scavenging activity in all three methods in comparison with ascorbic acid and 15-LOX inhibition potency using quercetin as standard then were subjected to in vivo study. Catalase (CAT) activity, glutathione (GSH) and malondialdehyde (MDA) levels were assayed in liver of treated rats. Compounds 5b, 5c, and 6e showed significant in vivo antioxidant potentials compared to control group at dose of 100 mg/kg B.W. Molecular docking of compound 6a endorsed its proper binding at the active site pocket of the human 15-LOX which explains its potent antioxidant activity in comparison with standard ascorbic acid.

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Section: Introductionmentioning

confidence: 99%

Design, synthesis, molecular modelling and biological evaluation of novel 3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives as potent antioxidants and 15-Lipoxygenase inhibitors

Ali

Awad

Said

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Pyrazole derivatives have broad application, from engineering and polymers [1,2,3,4,5,6,7,8], to biological activity [9]; thus, new synthetic strategies are constantly developed [10,11,12,13,14,15,16,17]. Among them, there are 1 H -pyrazoles with substituents at positions 3 and 5, which reveal interesting applications [18,19,20,21,22,23,24,25], and some of them are depicted in Figure 1. The substitution at positions 3 and 5 by amide, ester, or generally a carbonyl linkage makes a convenient structural building block of potentially broad usage.…”

Section: Introductionmentioning

confidence: 99%

Annular Tautomerism of 3(5)-Disubstituted-1H-pyrazoles with Ester and Amide Groups

et al. 2019

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A series of disubstituted 1H-pyrazoles with methyl (1), amino (2), and nitro (3) groups, as well as ester (a) or amide (b) groups in positions 3 and 5 was synthesized, and annular tautomerism was investigated using X-ray, theoretical calculations, NMR, and FT-IR methods. The X-ray experiment in the crystal state showed for the compounds with methyl (1a, 1b) and amino (2b) groups the tautomer with ester or amide groups at position 3 (tautomer 3), but for those with a nitro group (3b, 4), tautomer 5. Similar results were obtained in solution by NMR NOE experiments in CDCl3, DMSO-d6, and CD3OD solvents. However, tautomer equilibrium was observed for 2b in DMSO. The FT-IR spectra in chloroform and acetonitrile showed equilibria, which can be ascribed to conformational changes of the cis/trans arrangement of the ester/amide group and pyrazole ring. Theoretical analysis using the M06-2X/6-311++G(d,p) method (in vacuo, chloroform, acetonitrile, and water) and measurement of aromaticity (NICS) showed dependence on internal hydrogen bonds, the influence of the environment, and the effect of the substituent. These factors, pyrazole aromaticity and intra- and inter-molecular interactions, seem to have a considerable influence on the choice of tautomer.

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“…It has low toxicity and low residue, and it has different flexibility due to its molecular structure . Combined, it exhibits a wide range of biological activities such as antibacterial, insecticidal, anticancer, antiviral, anti‐inflammatory and other biological activities. Therefore, chalcone has potential research value in the field of new pesticide synthesis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biological Activity and Action Mechanism Study of Novel Chalcone Derivatives Containing Malonate

Guo

Xia

Liu

et al. 2020

Chemistry & Biodiversity

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A series of novel chalcone malonate derivatives were synthesized and their antibacterial and antiviral activities were evaluated. All target compounds were characterized by spectral data. The results of antimicrobial bioassay showed that one compound (diethyl [3-(naphthalen-2-yl)-1-(3-nitrophenyl)-3-oxopropyl]propanedioate) showed excellent antibacterial activity against Xanthomonas oryzae pv. oryzae (Xoo), with an EC 50 value of 10.2 μg/mL, which is significantly superior to bismerthiazol (71.7 μg/mL) and thiodiazole copper (97.8 μg/mL). At the same time, the mechanism of two compounds was confirmed by scanning electron microscopy. In addition, another compound (diethyl [3-(naphthalen-2-yl)-1-(4-nitrophenyl)-3-oxopropyl]propanedioate) showed significant curative activity to tobacco mosaic virus, with a value of 74.3 %, which was superior to 53.3 % of ningnanmycin. The results of microscale thermophoresis also showed that the Kd value of the combination of two compounds with the coat protein of tobacco mosaic virus was 0.211 and 0.166 μmol/L, which was better than 0.596 μmol/L of ningnanmycin. At the same time, the molecular docking of two compounds with tobacco mosaic virus-coat protein shows that the compound is well embedded in the pocket between the two subunits of tobacco mosaic virus-coat protein. These results show that chalcone derivatives containing malonate group can be considered as activators in the design of antibacterial and antiviral agents.

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Multiple biological activities and molecular docking studies of newly synthesized 3-(pyridin-4-yl)-1H-pyrazole-5-carboxamide chalcone hybrids

Cited by 43 publications

References 37 publications

Design, synthesis, molecular modelling and biological evaluation of novel 3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives as potent antioxidants and 15-Lipoxygenase inhibitors

Design, synthesis, molecular modelling and biological evaluation of novel 3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives as potent antioxidants and 15-Lipoxygenase inhibitors

Annular Tautomerism of 3(5)-Disubstituted-1H-pyrazoles with Ester and Amide Groups

Synthesis, Biological Activity and Action Mechanism Study of Novel Chalcone Derivatives Containing Malonate

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