Synthesis, assessment of substituent effect and antimicrobial activities of (4E)-4-(benzylideneamino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one compounds

Senbagam, R.; Vijayakumar, R.; Rajarajan, M.; Balaji, S.; Manikandan, V.; Vanangamudi, Ganesan; Thirunarayanan, Ganesamoorthy

doi:10.1016/j.kijoms.2016.01.004

Cited by 7 publications

(8 citation statements)

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“…The diversified Schiff base structures and their different mechanisms of action can explain the wide variety of biological activities described for these compounds that deserve more attention as promising candidates for therapies are being more and more delineated. Some of the Schiff bases reported with interesting bioactivities are those derived from 4-aminoantipyrine, and early reports have shown that these compounds have also important antioxidant properties [14], as well as antifungal and antibacterial activity against several microorganisms [30,31,32,33]. However, most of these studies were performed by antibiograms.…”

Section: Introductionmentioning

confidence: 99%

Characterization of Antimicrobial, Antioxidant, and Leishmanicidal Activities of Schiff Base Derivatives of 4-Aminoantipyrine

et al. 2019

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Our main interest is the characterization of compounds to support the development of alternatives to currently marketed drugs that are losing effectiveness due to the development of resistance. Schiff bases are promising biologically interesting compounds having a wide range of pharmaceutical properties, including anti-inflammatory, antipyretic, and antimicrobial activities, among others. In this work, we have synthesized 12 Schiff base derivatives of 4-aminoantipyrine. In vitro antimicrobial, antioxidant, and cytotoxicity properties are analyzed, as well as in silico predictive adsorption, distribution, metabolism, and excretion (ADME) and bioactivity scores. Results identify two potential Schiff bases: one effective against E. faecalis and the other with antioxidant activity. Both have reasonable ADME scores and provides a scaffold for developing more effective compounds in the future. Initial studies are usually limited to laboratory in vitro approaches, and following these initial studies, much research is needed before a drug can reach the clinic. Nevertheless, these laboratory approaches are mandatory and constitute a first filter to discriminate among potential drug candidates and chemical compounds that should be discarded.

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Section: Introductionmentioning

confidence: 99%

Characterization of Antimicrobial, Antioxidant, and Leishmanicidal Activities of Schiff Base Derivatives of 4-Aminoantipyrine

et al. 2019

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“…It could be concluded that pyrazole is one of the lead compounds for antimicrobial agent. A series of Schiff's bases of substituted (4E)-4-(benzylideneamino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-ones have been prepared starting from 4-AAP and benzaldehyde derivatives [73]. Based on Kirby-Bauer protocol for antimicrobial assay, it was noted that compounds (59) and (60) exhibited the high activity against bacterial as well as fungal strains, such as B. subtilis, P. aeruginosa, and A. niger.…”

Section: Fig 4: Structure Of Compounds (48-60)mentioning

confidence: 99%

“…Based on Kirby-Bauer protocol for antimicrobial assay, it was noted that compounds (59) and (60) exhibited the high activity against bacterial as well as fungal strains, such as B. subtilis, P. aeruginosa, and A. niger. Schiff's bases containing 4-Cl and 4-NO 2 moieties presented good inhibitory activity [73].…”

Section: Fig 4: Structure Of Compounds (48-60)mentioning

confidence: 99%

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A Recent Update: Antimicrobial Agents Containing Pyrazole Nucleus

Ardiansah

2018

Asian J Pharm Clin Res

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Objective: In this review, we report antimicrobial candidates containing pyrazole nucleus integrated with various functionalities.Methods: research results by numerous scientists have been summarized from international journals indexed in reputed database such as Scopus and Web of Science.Results: Pyrazole derivatives are much of interest as potent bioactive molecules. They have shown large bioactivities especially antimicrobial performance against broad spectrum of bacterial strains.Conclusion: Several designed pyrazole derivates possessed good to superior antimicrobial activities.

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“…This is due to the reasons stated earlier and it is associated with the resonance-conjugated structure as shown in Figure 2 In view of the inability of some of the σ constants to produce individually satisfactory correlation for C=O, CH 3(keto) , C=N, CH 2 , C α , C β , OCH 3 , C=O (ester) , and CH 3(ester) carbons, the authors think that, it is worthwhile to seek multiple correlation involving either σ I , σ R or F and R parameters [30]. The formulated multi-correlation equations are given in (23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38)(39)(40). …”

Section: C Nmr Spectramentioning

confidence: 99%

Solvent-Free Synthesis and Spectral Correlation of 1N-Acetyl-3-(4-β-Methacrylate)-5-(Substituted Phenyl)-4,5-Dihydro-1H-Pyrazolines

Thirunarayanan¹,

Sekar²

2017

MOCR

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Abstract.A series containing fourteen 1 N-acetyl-3-(4-β-methacrylate)-5-(substituted phenyl)-4, 5-dihydro-1 H-pyrazolines were synthesized by KF/Al 2 O 3 catalyzed solvent-free condensation of 1 Nacetyl-3-(4-hydroxyphenyl)-5-(substituted phenyl)-4, 5-dihydro-1 H-pyrazolines and (E)-methyl-2-[2-(bromo methyl)-phenyl]-3-methoxyacrylate under microwave irradiation. The yields of the above 1 Nacetyl-3-(4-β-methacrylate)-5-(substituted phenyl)-4, 5-dihydro-1 H-pyrazolines were more than 90%. These pyrazolines were characterized by their physical constants, IR, NMR and Mass spectral data. The infrared spectral frequencies (ν, cm -1 ) and NMR chemical shifts (δ, ppm) of proton and carbons of these pyrazolines were assigned and correlated with Hammett substituent constants, F and R parameters. From the results of statistical analyses, the effects of substituent on the above spectral data have been discussed.Keywords: Solvent-free synthesis, KF/Al 2 O 3 , β-methacrylate-1 N-acetylpyrazolines, IR spectra, NMR spectra, Hammett correlation IntroductionThe 1 H-4,5-dihydropyrazoline and 1 N-acetyl-4,5-dihydroprazoline derivatives play structurally more important roles in pharmaceutical field of research because they possess numerous biological activities. were utilized for the above reactions. Now-a-days chemists and organic researchers have paid more attention to solvent-free methods. These methods are important and play vital role for synthesis of organics due to easy work-up procedure, technique, shorter time, less hazardousness, less pollution to the environment, higher yield. Sasikala et al.,[15] have synthesised some 5-chloro-2-thienyl based pyrazoline derivatives by solvent-free method and studied the antimicrobial activities. Sakthinathan et al.[20] have synthesised and studied the effects of substituent on 2-naphthyl based pyrazolines. Spectroscopic data were used for prediction of ground state equilibration of organic compounds such as, E, Z or cis-trans isomers of unsaturated compounds such as, alkenes, alkynes, polyenes, enol-enones, unsaturated acid chlorides, ω-halo-acyl compounds and pyrazoline derivatives. These spectroscopic data were applied for the study of spectral linear regression through Hammett equation. Thirunarayanan et al. have studied the effects of substituents and solventfree synthesis of some 5-bromo-2-thienyl based pyrazolines [22]. The solvent-free synthesis and the Modern

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Synthesis, assessment of substituent effect and antimicrobial activities of (4E)-4-(benzylideneamino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one compounds

Cited by 7 publications

References 12 publications

Characterization of Antimicrobial, Antioxidant, and Leishmanicidal Activities of Schiff Base Derivatives of 4-Aminoantipyrine

Characterization of Antimicrobial, Antioxidant, and Leishmanicidal Activities of Schiff Base Derivatives of 4-Aminoantipyrine

A Recent Update: Antimicrobial Agents Containing Pyrazole Nucleus

Solvent-Free Synthesis and Spectral Correlation of <sup>1</sup><i>N</i>-Acetyl-3-(4-β-Methacrylate)-5-(Substituted Phenyl)-4,5-Dihydro-<sup>1</sup><i>H</i>-Pyrazolines

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