Discovery, synthesis and molecular corroborations of medicinally important novel pyrazoles; drug efficacy determinations through in silico, in vitro and cytotoxicity validations

Thangarasu, Pandiyan; Thamaraiselvi, S.

doi:10.1016/j.bioorg.2019.02.003

Cited by 20 publications

(9 citation statements)

References 39 publications

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“…The DNA gyrase A ( S . aureus ) assay of compounds ( 4a‐l ) was carried out as we reported earlier DNA gyrase purification, supercoiling, and decatenation was executed as reported by F. Blanche 1996 …”

Section: Enzyme Inhibition Assaymentioning

confidence: 99%

“…Noticeably, the attention on DNA gyrase inhibition validation against small molecule chemical entities is growing well in search of DNA gyrase inhibition based antibiotics . Obviously, bacterial DNA gyrase and DNA topoisomerase IV is, currently, one of the main targets against the resistance of microbes . In fact, inhibition of DNA gyrase and topoisomerase IV is the fundamental mechanism of many antibacterial drugs .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and discovery of N‐(1‐methyl‐4‐oxo‐4,5‐dihydro‐1H‐imidazol‐2‐yl)‐[1,1′‐biphenyl]‐2‐carboxamide derivatives as antimicrobial agents

Ashok

Shivananda

Prakash

et al. 2020

Journal of Heterocyclic Chem

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Novel dihydro‐1H‐imidazole‐2‐yl)‐[1,1′‐biphenyl]‐2‐carboxamides (4a‐l) was achieved using a three‐step synthesis process and evaluated as antimicrobial agents. These compounds were characterized through FTIR, NMR, LCMS and evaluated for DNA gyrase inhibition potentials and antimicrobial properties against Gram‐negative bacteria Escherichia coli (MTCC 443), Pseudomonas aeruginosa (MTCC 424), Klebsiella pneumoniae MTCC 530 and Gram‐positive bacteria Staphylococcus aureus (MTCC 3160), Corynebacterium diphtheriae (MTCC 116) and Streptococcus pyogenes (MTCC 442). Excellent DNA gyrase inhibition exhibited by compound 4f (IC50 0.2 μM and relative percentage activity 96.24%). A broad spectrum of antimicrobial activity showed by compounds 4d, 4f and 4 k with a Minimal Inhibitory Constant (MIC) of 1.05, 1.35 and 1.25 μg mL−1, respectively.

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Section: Enzyme Inhibition Assaymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and discovery of N‐(1‐methyl‐4‐oxo‐4,5‐dihydro‐1H‐imidazol‐2‐yl)‐[1,1′‐biphenyl]‐2‐carboxamide derivatives as antimicrobial agents

Ashok

Shivananda

Prakash

et al. 2020

Journal of Heterocyclic Chem

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“…Pyrazole rings can be seen very rarely in natural compounds since the formation of -N-N-bond is difficult in living organisms [1]. On the other hand, there are numerous physiological and pharmacological activities of compounds containing pyrazole scaffolds in their structures [2][3][4][5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

Direct demonstration of tautomeric nature of 4‐bromo‐3(5)‐methylpyrazoles

Aleksanyan

Hakobyan

Shahkhatuni

et al. 2022

Journal of Heterocyclic Chem

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Tautomerization is the key feature of pyrazoles, which is connected with the hydrogen transfer in pyrazoles between two nitrogens. It is scholarly accepted that tautomers of 3(5)-substituted pyrazole derivatives cannot be isolated as individual compounds with the exception of certain extreme conditions. Here using the fact that N-substitution suppresses tautomerization and allows their separation and isolation, the individual isomers of N-propanoates of 3(5)pyrazole were synthesized, isolated, and further modified several times without change of initial 3-or 5-methyl configuration. However, once the group attached to the nitrogen was removed, two individual isomers gained back their tautomeric properties and became the same mixture of tautomers, as expected. Close monitoring by NMR spectroscopy vividly demonstrates the loss and then reverting of tautomeric properties of 3(5)-pyrazole derivatives along the set of chemical transformations aimed at possible isolation of two tautomers. Failure to isolate them once again proves that the dynamic equilibrium of tautomers in solution is an inherent property of 3(5)-methylpyrazole.

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“…Moraes et al, 2019), analgesic (M. Srivastava et al, 2014), anti-inflammatory (F. Shirini et al, 2015), anti-diabetic (M. Driowya et al, 2018 ), anti-hyperglycemic (F. Nemati et al, 2015), antidepressive (A.R.F. Carreira et al, 2019) and anti-angiogenic (P. Thangarasu et al, 2019) activities. Bispyrazolones have exhibited significant antioxidant agents to slow down the process of oxidation by protecting from the reactive oxygen species (ROS) (K. Niknam et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some new bis(pyrazol-5-ols), pyridones and benzo-[f]-thiochromene-2-carbonitrile derivatives bearing N-(4-chlorophenyl)-2-(4-formylphenoxy)acetamide moiety

Arafat¹,

Khalifa²,

El‐Taweel³

et al. 2022

Scientific Journal for Damietta Faculty of Science

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Novel 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) derivative 2 was synthesized via interaction of N-(4-chlorophenyl)-2-(4-formylphenoxy)acetamide (1) with diverse available reagent (two mole from 3-methyl-1H-pyrazol-5(4H)-one). Moreover, One-pot pseudo threecomponent reaction of hydrazine hydrate, ethyl acetoacetate and aldehydes in ethanole using pipridine at 70°C afforded the corresponding aminopyrazole derivative 3. on the other hand, cyanoacetamide scaffolds 4a,b was reacted with aromatic aldehyde particularly N-(4-chlorophenyl)-2-(4-formylphenoxy)acetamide (1), to afford arylidenes 5a,b that undergoes cyclization by heating in ethanol containing drops of piperidine as catalyst, and malononitrile afforded the corresponding pyridinone derivatives 6a,b. All freshly synthesized scaffolds were elucidated by considering the data of both elemental and spectral analyses.

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Discovery, synthesis and molecular corroborations of medicinally important novel pyrazoles; drug efficacy determinations through in silico, in vitro and cytotoxicity validations

Cited by 20 publications

References 39 publications

Synthesis and discovery of N‐(1‐methyl‐4‐oxo‐4,5‐dihydro‐1H‐imidazol‐2‐yl)‐[1,1′‐biphenyl]‐2‐carboxamide derivatives as antimicrobial agents

Synthesis and discovery of N‐(1‐methyl‐4‐oxo‐4,5‐dihydro‐1H‐imidazol‐2‐yl)‐[1,1′‐biphenyl]‐2‐carboxamide derivatives as antimicrobial agents

Direct demonstration of tautomeric nature of 4‐bromo‐3(5)‐methylpyrazoles

Synthesis of some new bis(pyrazol-5-ols), pyridones and benzo-[f]-thiochromene-2-carbonitrile derivatives bearing N-(4-chlorophenyl)-2-(4-formylphenoxy)acetamide moiety

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