V2O5/SiO2 as an efficient catalyst in the synthesis of 5-amino- pyrazole derivatives under solvent free condition

Khatab, Tamer K.; Hassan, Ashraf S.; Hafez, T. S.

doi:10.4314/bcse.v33i1.13

Cited by 30 publications

(21 citation statements)

References 24 publications

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“…The starting materials, 5-amino-N-aryl-1H-pyrazole-4-carboxamides 1a-c, were prepared according to our previous work [26]. The syntheses of the targets, 5,7-dimethylpyrazolo[1,5-a]pyrimidines 5a-c, 5,7-dihydroxypyrazolo[1,5-a]pyrimidines 9a-c and 7-aryl-pyrazolo[1,5-a]pyrimidines 13a-i, are illustrated in Schemes 1 and 2.…”

Section: Chemistrymentioning

confidence: 99%

Biological Evaluation and Molecular Docking with In Silico Physicochemical, Pharmacokinetic and Toxicity Prediction of Pyrazolo[1,5-a]pyrimidines

et al. 2020

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Pyrazolo[1,5-a]pyrimidines 5a–c, 9a–c and 13a–i were synthesized for evaluation of their in vitro antimicrobial properties against some microorganisms and their immunomodulatory activity. The biological activities of pyrazolo[1,5-a]pyrimidines showed that the pyrazolo[1,5-a]pyrimidines (5c, 9a, 9c, 13a, 13c, 13d, 13e and 13h) displayed promising antimicrobial and immunomodulatory activities. Studying the in silico predicted physicochemical, pharmacokinetic, ADMET and drug-likeness properties for the pyrazolo[1,5-a]pyrimidines 5a–c, 9a–c and 13a–i confirmed that most of the compounds (i) were within the range set by Lipinski’s rule of five, (ii) show higher gastrointestinal absorption and inhibition of some CYP isoforms, and (iii) have a carcinogenicity test that was predicted as negative and hERG test that presented medium risk. Moreover, the molecular docking study demonstrated that the compounds 5c, 9a, 9c, 13a, 13c, 13d, 13e and 13h are potent inhibitors of 14-alpha demethylase, transpeptidase and alkaline phosphatase enzymes. This study could be valuable in the discovery of a new series of drugs.

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Section: Chemistrymentioning

confidence: 99%

Biological Evaluation and Molecular Docking with In Silico Physicochemical, Pharmacokinetic and Toxicity Prediction of Pyrazolo[1,5-a]pyrimidines

et al. 2020

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“…In view of these facts and in continuation of our target [13][14][15][16][17][18][19][20][21][22][23][24][25], the metal complexes {Ni(II), Co(II) and Mn(II)} of 3-(2-(aryl)hydrazono)acetylacetone with isatin have been synthesized to evaluate their antibacterial activity against four pathogenic microorganisms {two Gram-positive (Bacillus subtilis and Staphylococcus aureus) and two Gram negative (Escherichia coli and Pseudomonas aeruginosa)}. Also, the study has been extended to calculate the physicochemical properties and drug-likeness (Lipinski's rule) of the mixed ligand metal complexes ( Figure 2).…”

Section: Introductionmentioning

confidence: 84%

Mixed isatin with 3-(2-(aryl)hydrazono)acetylacetone Mn(II), Co(II) and Ni(II) complexes: antibacterial evaluation and molecular properties prediction

Hassan¹

2021

Bull. Chem. Soc. Eth.

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The metal complexes {Ni (II), Co (II) and Mn (II)} of 3-(2-(aryl)hydrazono)acetylacetone with isatin were synthesized and screened for their in vitro antibacterial activity against four pathogenic microorganisms {two Gram‐positive and two Gram negative}. The results of antibacterial activities revealed that all the metal complexes 1-9 exhibited moderate activities. Also, Lipinski's rule of five (RO5) of the mixed ligand metal complexes were calculated by SwissADME website. KEY WORDS: Isatin, 3-(2-(Aryl)hydrazono)acetylacetone, Metal complexes, Antibacterial activities, Lipinski rules Bull. Chem. Soc. Ethiop. 2020, 34(3), 533-541. DOI: https://dx.doi.org/10.4314/bcse.v34i3.9

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“…The starting material, 5-amino-N-aryl-3-(4-methoxyphenylamino)-1H-pyrazole-4-carboxamide 1a-d, was prepared according to the reported method [51][52][53]. New Schiff bases with hybrid active core pyrazole derivatives were synthetized by the reaction of pyrazole derivatives 1a-d with different aldehyde containing different pharmacophore atoms or groups that are represented in Scheme 1 namely 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carbaldehyde (2), 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (3), 4-(piperidin-1-yl)benzaldehyde (4), and 3,4,5-trimethoxybenzaldehyde (5) hoping to be effective as antimicrobial and anticancer activities.…”

Section: Chemistrymentioning

confidence: 99%

Discovery of New Schiff Bases Tethered Pyrazole Moiety: Design, Synthesis, Biological Evaluation, and Molecular Docking Study as Dual Targeting DHFR/DNA Gyrase Inhibitors with Immunomodulatory Activity

et al. 2020

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A series of Bis-pyrazole Schiff bases (6a–d and 7a–d) and mono-pyrazole Schiff bases (8a–d and 9a–d) were designed and synthesized through the reaction of 5-aminopyrazoles 1a–d with aldehydes 2–5 using mild reaction condition with a good yield percentage. The chemical structure of newly formed Schiff bases tethered pyrazole core was confirmed based on spectral and experimental data. All the newly formed pyrazole Schiff bases were evaluated against eight pathogens (Gram-positive, Gram-negative, and fungi). The result exhibited that, most of them have good and broad activities. Among those, only six Schiff bases (6b, 7b, 7c, 8a, 8d, and 9b) displayed MIC values (0.97–62.5 µg/mL) compared to Tetracycline (15.62–62.5 µg/mL) and Amphotericin B (15.62–31.25 µg/mL), MBC values (1.94–87.5 µg/mL) and selectivity to tumor cell than normal cells. Immunomodulatory activities showed that the promising Schiff bases increase the immunomodulator effect of defense cell and the Schiff base 8a is the highest one by (Intra. killing activity = 136.5 ± 0.3%) having a pyrazole moiety as well as amide function (O=C-NH2) and piperidinyl core. Furthermore, the most potent one exhibited broad activity depending on both MIC and MBC values. Moreover, to study the mechanism of these pyrazole Schiff bases, two active Schiff bases 8a and 9b from six derivatives were introduced to study the enzyme assay as dihydrofolate reductase (DHFR) on E. coli organism and DNA gyrase with two different organisms, S. aureus and B. subtilis, to determine the inhibitory activities with lower values in the case of DNA gyrase (8a and 9b) or nearly as DHFR compound 9b, while pyrazole 8a showed excellent inhibitory against all enzyme assay. The molecular docking study against dihydrofolate reductase and DNA gyrase were performed to study the binding between active site in the pocket with the two Schiff bases (8a and 9b) that exhibited good binding affinity with different bond types as H-bonding, aren-aren, and arene-cation interaction as well as study the physicochemical and pharmacokinetic properties of the two active Schiff bases 8a and 9b.

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V2O5/SiO2 as an efficient catalyst in the synthesis of 5-amino- pyrazole derivatives under solvent free condition

Cited by 30 publications

References 24 publications

Biological Evaluation and Molecular Docking with In Silico Physicochemical, Pharmacokinetic and Toxicity Prediction of Pyrazolo[1,5-a]pyrimidines

Biological Evaluation and Molecular Docking with In Silico Physicochemical, Pharmacokinetic and Toxicity Prediction of Pyrazolo[1,5-a]pyrimidines

Mixed isatin with 3-(2-(aryl)hydrazono)acetylacetone Mn(II), Co(II) and Ni(II) complexes: antibacterial evaluation and molecular properties prediction

Discovery of New Schiff Bases Tethered Pyrazole Moiety: Design, Synthesis, Biological Evaluation, and Molecular Docking Study as Dual Targeting DHFR/DNA Gyrase Inhibitors with Immunomodulatory Activity

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