Synthesis, Antimicrobial Activity and Molecular Modeling of Some Novel 5‐Aminopyrazole, Pyrazolo[1,5‐<i>a</i>]pyrimidine, Bispyrazole and Bispyridone Derivatives Containing Antipyrinyl Moiety

Helal, Mohamed H.; Salem, Mohamed Salem Ould Ahmedou; Aly, Hala M.

doi:10.1002/jhet.2858

Cited by 5 publications

(3 citation statements)

References 39 publications

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“…2-(4-Oxothiazolidin-2-ylidene)acetonitrile (1a) and ethyl-2-(4-oxothiazolidin-2-ylidene)acetate (1b) were prepared according to the reported method. 35 Furthermore, 1,3-diphenyl-1H-pyrazole-4-carbaldehyde (2a), 1-phenyl-3-(p-tolyl)-1H-pyrazole-4-carbaldehyde (2b), 37 2-cyano-N- (1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide ( 9), 41,56 The MIC of the target compounds (having inhibition zones > 9 mm) was then determined using the broth microdilution method. 58 Two-fold serial dilutions of the tested compounds were prepared to give a concentration range 0.125−128 μg/mL.…”

Section: Discussionmentioning

confidence: 99%

“…2-(4-Oxothiazolidin-2-ylidene)acetonitrile ( 1a ) and ethyl-2-(4-oxothiazolidin-2-ylidene)acetate ( 1b ) were prepared according to the reported method . Furthermore, 1,3-diphenyl-1 H -pyrazole-4-carbaldehyde ( 2a ), 1-phenyl-3-( p -tolyl)-1 H -pyrazole-4-carbaldehyde ( 2b ), 2-cyano- N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)acetamide ( 9 ), , and N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)carbonohydrazonoyldicyanide ( 12 ) were also prepared.…”

Section: Methodsmentioning

confidence: 99%

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In Vitro Antimicrobial Evaluation, Single-Point Resistance Study, and Radiosterilization of Novel Pyrazole Incorporating Thiazol-4-one/Thiophene Derivatives as Dual DNA Gyrase and DHFR Inhibitors against MDR Pathogens

et al. 2022

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A series of thiazol-4-one/thiophene-bearing pyrazole derivatives as pharmacologically attractive cores were initially synthesized using a hybridization approach. All structures were confirmed using spectra analysis techniques (IR, 1 H NMR, and 13 C NMR). In vitro antimicrobial activities, including the minimum inhibitory concentration (MIC), minimum bactericidal/fungicidal concentration (MBC/MFC), and time-kill assay, were evaluated for the most active derivatives 4a, 5a, 7b, 10, and 13. These derivatives were significantly active against the tested pathogens, with compound 7b as the most active derivative (MIC values range from 0.22 to 0.25 μg/mL). In the MBC and MFC, the active target pyrazole derivatives showed -cidal activities toward the pathogenic isolates. Further, the inhibition of biofilm formation of Staphylococcus aureus and Staphylococcus epidermidis was also carried out. Additionally, these derivatives displayed significant antibiofilm potential with a superior % reduction in the biofilm formation compared with Ciprofloxacin. The target derivatives behaved synergistically with Ciprofloxacin and Ketoconazole, reducing their MICs. Hemolytic results revealed that these derivatives were nontoxic with a significantly low hemolytic activity (%lysis range from 3.23 to 15.22%) compared with Triton X-100 and showed noncytotoxicity activity with IC 50 values > 60 μM. In addition, these derivatives proved to be active DNA gyrase and DHFR inhibitors with IC 50 ranging between 12.27−31.64 and 0.52−2.67 μM, respectively. Furthermore, compound 7b showed bactericidal activity at different concentrations in the time-kill assay. Moreover, a gamma radiation dose of 10.0 kGy was efficient for sterilizing compound 7b and enhancing its antimicrobial activity. Finally, molecular docking simulation of the most promising derivatives exhibited good binding energy with different interactions.

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Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

In Vitro Antimicrobial Evaluation, Single-Point Resistance Study, and Radiosterilization of Novel Pyrazole Incorporating Thiazol-4-one/Thiophene Derivatives as Dual DNA Gyrase and DHFR Inhibitors against MDR Pathogens

et al. 2022

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“…Recently, Helal et al (2017) reported that reaction of 5-aminopyrazole derivative (23) with 4-methoxybenzaldehyde and terenaphthaldehyde afforded the corresponding mono and bis-(azomethine) derivatives ( 24) and ( 25). Noteworthy, the reaction, in both cases, occurs on the exocyclic NH 2 group (Scheme 9).…”

Section: Relative Nucleophilicity Of Nh 2 Groupmentioning

confidence: 99%

Believes versus evidence-based regio-orientation in the structure assignment of pyrazolo[1,5-a]pyrimidines

2019

Japs

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This review aims to focus and highlight the regio-orientation and regioselectivity of the reactions of 3(5)-aminopyrazoles with 1,3-bielectrophilic reagents that lead to the formation of pyrazolo [1,5-a]pyrimidines. To clarify the significance of regio-orientation, reactions of 3( 5)-aminopyrazoles with symmetric 1,3-bielectrophilic reagents such as acetylacetone and malononitrile are also included. The comparable nucleophilicity of the exocyclic NH 2 group and endocyclic NH in 3( 5)-aminopyrazoles is considered as it causes literature controversy associated with regio-orientation of the substituents on the pyrimidine ring of pyrazolo[1,5-a]pyrimidine when unsymmetrical 1,3-bielectrophilic reagent reacts with 3(5)-aminopyrazole. To the best of our knowledge, this review would be the first collective and confined report to the regio-orientation of pyrazolo [1,5-a]pyrimidines.

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Organocatalytic Enantioselective Aminoalkylation of 5‐Aminopyrazole Derivatives with Cyclic Imines

et al. 2020

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In this communication, an efficient asymmetric aminoalkylation of 5‐aminopyrazole derivatives with cyclic benzoxathiazine 2,2‐dioxides catalyzed by a quinine‐derived squaramide in dichloromethane has been established. This is the first example of 5‐aminopyrazole derivatives in asymmetric catalysis. A variety of chiral sulfamidates bearing an aminopyrazole moiety were obtained in good yields (up to 98 %) and moderate to excellent enantioselectivities (up to 99 %ee).

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Synthesis, Antimicrobial Activity and Molecular Modeling of Some Novel 5‐Aminopyrazole, Pyrazolo[1,5‐a]pyrimidine, Bispyrazole and Bispyridone Derivatives Containing Antipyrinyl Moiety

Cited by 5 publications

References 39 publications

In Vitro Antimicrobial Evaluation, Single-Point Resistance Study, and Radiosterilization of Novel Pyrazole Incorporating Thiazol-4-one/Thiophene Derivatives as Dual DNA Gyrase and DHFR Inhibitors against MDR Pathogens

In Vitro Antimicrobial Evaluation, Single-Point Resistance Study, and Radiosterilization of Novel Pyrazole Incorporating Thiazol-4-one/Thiophene Derivatives as Dual DNA Gyrase and DHFR Inhibitors against MDR Pathogens

Believes versus evidence-based regio-orientation in the structure assignment of pyrazolo[1,5-a]pyrimidines

Organocatalytic Enantioselective Aminoalkylation of 5‐Aminopyrazole Derivatives with Cyclic Imines

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