Synthesis, crystal structure, spectroscopic, antidiabetic, antioxidant and computational investigations of Ethyl 5-hydroxy-1-isonicotinoyl-3-methyl-4,5-dihydro-1H-pyrazole-5-carboxylate

Karrouchi, Khalid; Mortada, Salma; Issaoui, Noureddine; El-guourrami, Otman; Arshad, Suhana; Bouatia, Mustapha; Sagaama, Abir; Benzeid, Hanane; Karbane, Miloud El; Faouzi, My El Abbes; Brandán, Silvia Antonia

doi:10.1016/j.molstruc.2021.131977

Cited by 11 publications

(8 citation statements)

References 39 publications

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“…The substituted chiral pyrazoline derivatives (27 a-j) were synthesized by reacting different chalcones (25 a-j) and hydrazine 23 to interact with Asp327, Asp542, Trp406, and Phe575 amino acid residues. 33 Another study by Karrouchi et al 36 synthesized a new chiral pyrazole derivative having α-glucosidase and α-amylase enzyme inhibitory actions. For the synthesis (Figure 7), ethyl-2,4-dioxopentanoate 28 was refluxed with isoniazid 37 to produce ethyl-5-hydroxy-1-isonicotinoyl-3-methyl-4,5-dihydro-1H-pyrazole-5-carboxylate.…”

Section: Pyrazolementioning

confidence: 99%

“…38 This compound showed in-vitro antidiabetic activity and the molecular studies revealed its interaction with Gln298, Lys254, Leu639, Lys643, Leu638, and Ile300 at the active site of α-glucosidase (PDB ID:4XP0), and with Val382, Gly383, and Ala400 at the active site of α-amylase (PDB ID:2QPU). 36 2.1.5 | Isoxazolidine Ghannay et al 39 reported the synthesis of various isoxazolidine and C-alkyl imine oxide derivatives (Figure 8) by a series of reactions. The reaction was started from chiral nitrone 40 and produced different intermediate compounds 21,[41][42][43] in different conditions, which were further converted to chiral isoxazolidine and C-alkyl imine oxide derivatives (38, 39, 40a-c, 41, 42, 43, 44, 45).…”

Section: Pyrazolementioning

confidence: 99%

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Advancement in chiral heterocycles for the antidiabetic activity

Gupta,

Rani,

Nainwal

et al. 2024

Chirality

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For the synthesis and development of pharmaceuticals, chirality is an important structural component. Chiral heterocyclic compounds have annoyed the interest of synthetic chemists who are working to create useful and efficient techniques for these molecules. As indicated by the expanding number of chiral drugs created in the last two decades, the link between chirality and pharmacological activity has become more important in the pharmaceutical and biopharmaceutical industries. Approximately 65% of currently used drugs are chiral, and many of them are promoted as racemates in many circumstances. There are a growing number of new chiral heterocyclic compounds with important biological properties and intriguing uses in medical chemistry and drug discovery. In this study, we review current breakthroughs in chiral heterocycles and their different physiological activities that have been published in the last year (from 2010 to early 2023). This study focuses on the current trends in the use of chiral heterocycles in drug design and the creation of several powerful and competent candidates for diabetic illnesses.

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Section: Pyrazolementioning

confidence: 99%

Section: Pyrazolementioning

confidence: 99%

Advancement in chiral heterocycles for the antidiabetic activity

Gupta,

Rani,

Nainwal

et al. 2024

Chirality

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“…AutoGrid was carried out for the preparation of the geometry of binding site by using a grid box with several points in (x,y,z) ¼ (60, 60,60) box, and the box spacing was 0.375 Å. The selected ligands are drawn using Chemdraw12.0 software (Hafidi et al, 2019;Karrouchi et al, 2021). In order to select the most stable conformation, the geometry of these ligands was subsequently optimized using Molecular Force Field (MMFF94) as implemented in the same Software.…”

Section: Molecular Docking Studymentioning

confidence: 99%

Biological, toxicological and molecular docking evaluations of isoxazoline-thiazolidine-2,4-dione analogues as new class of anti-hyperglycemic agents

Fettach

Thari

Hafidi

et al. 2021

Journal of Biomolecular Structure and Dynamics

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In this work, three isoxazoline-thiazolidine-2,4-dione derivatives were synthesized and characterized by FT-IR, 1 H-NMR, 13 C-NMR and ESI-MS spectrometry. All compounds have been investigated for their a-amylase and a-glucosidase inhibitory activities. In vitro enzymatic evaluation revealed that all compounds were inhibitory potent against a-glucosidase with IC 50 values varied from 40.67 ± 1.81 to 92.54 ± 0.43 mM, and a-amylase with IC 50 in the range of 07.01 ± 0.02 to 75.10 ± 1.06 mM. One of the tested compounds were found to be more potent inhibitor compared to other compounds and standard drug Acarbose (IC 50 glucosidase ¼ 97.12 ± 0.35 mM and IC 50 amylase ¼ 2.97 ± 0.01 lM). All compounds were then evaluated for their acute toxicity in vivo and shown their safety at a high dose with LD > 2000mg/kg BW. A cell-based toxicity evaluation was performed to determine the safety of compounds on liver cells, using the MTT assay against HepG2 cells, and the results shown that all compounds have non-toxic impact against cell viability and proliferation compared to reference drug (Pioglitazone). Furthermore, the molecular homology analysis, SAR and the molecular binding properties of compound with the active site of a-amylase and a-glucosidase were confirmed through computational analysis. This study has identified the inhibitory potential of a new class of synthesized isoxazoline-thiazolidine-2,4-dione derivatives in controlling both hyperglycemia and type 2 diabetes mellitus without any hepatic toxicity.

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“…[10] The pyrazole and thiazole moieties are crucial components of antiviral medications, as illustrated in Figure 1. In addition, pyrazole and thiazole have been demonstrated to exhibit broad biological activity, including anticancer, [26,27] antioxidant, [28,29] antidiabetic, [30,31] antituberculosis, [32,33] antibacterial, [34,35] antifungal, [36,37] and anticonvulsant [38,39] properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Virtual Screening of Pyrazolothiazole Conjugates as Promising SARS‐CoV‐2 Inhibitors

Seliem

2023

ChemistrySelect

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The current coronavirus outbreak has highlighted the significance of continuing to develop novel antiviral agents. The SARS‐CoV‐2 main protease (Mpro), essential for virus replication, has been recognized as a potential target for developing novel COVID‐19 therapeutics. Herein, we report synthesizing a series of pyrazolothiazole conjugates and in silico molecular docking screening of their interactions with the COVID‐19 protease 6LU7 protein. The new hybrids were obtained by condensing substituted pyrazole‐4‐carbaldehyde with N‐phenyl‐hydrazinecarbothioamide and subsequent refluxing with selected α‐haloketones in a basic medium. The structures of the novel pyrazolothiazoles were fully verified by FTIR, 1H NMR, 13C NMR, and elemental analyses. Molecular docking and free energy analyses using the MM/GBSA approach revealed that 5 a–c and 7 a–c formed stable interactions within the protease 6LU7 pocket, thus, could be potential inhibitors of SARS‐CoV‐2.

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Synthesis, crystal structure, spectroscopic, antidiabetic, antioxidant and computational investigations of Ethyl 5-hydroxy-1-isonicotinoyl-3-methyl-4,5-dihydro-1H-pyrazole-5-carboxylate

Cited by 11 publications

References 39 publications

Advancement in chiral heterocycles for the antidiabetic activity

Advancement in chiral heterocycles for the antidiabetic activity

Biological, toxicological and molecular docking evaluations of isoxazoline-thiazolidine-2,4-dione analogues as new class of anti-hyperglycemic agents

Synthesis and Virtual Screening of Pyrazolothiazole Conjugates as Promising SARS‐CoV‐2 Inhibitors

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