Synthesis, spectral studies and antimicrobial activities of some 2-naphthyl pyrazoline derivatives

Sakthinathan, S.P.; Vanangamudi, Ganesan; Thirunarayanan, Ganesamoorthy

doi:10.1016/j.saa.2012.04.082

Cited by 68 publications

(100 citation statements)

References 23 publications

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“…P. Shaktinathan and his research group 43 synthesized a series of novel 2-naphthyl pyrazolines and also evaluated these compounds for their antimicrobial activity against bacterial strains (Gram-positive Micrococcous luteus, Bacillus substilis, Staphylococcus aureus and Gram-negative Escherichia coli and Klebsiella) and against fungal strains (Aspergillus niger and Trichoderma viride) by utilising the well-known disc diffusion technique (Table 23). The activity was confirmed by measuring the diameter of the zone of inhibition.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

“…The most extensive modification in 2-pyrazoline was the substitution of diaryl/hetroaryl groups mainly at -3, 5 position 40 since it was observed that heterocycles with functional groups greatly increased solubility in water 41,42 . The aryl substituted pyrazolines were detected to combine the activity of pyrazoline moiety with activity of heteroarene thus proving their usefulness 43 . The perpetual research carried out revealed the indispensable role N-substituents of pyrazoline play in exhibiting the biological activity.…”

Section: Introductionmentioning

confidence: 99%

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4,5-Dihydro-1H-pyrazole: an indispensable scaffold

Alex

Kumar

2013

Journal of Enzyme Inhibition and Medicinal Chemistry

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Pyrazoles, categorized as nitrogen-containing heterocycles, are well known for their interminable participation in the field of perpetual research and development of therapeutical active agents. As a consequence pyrazoles became an inevitable core of numerous drugs having diverse activities. The broad spectrum of activities portrayed by the pyrazoles instigated the researchers to modify the pyrazole ring as 4,5-dihydro-1H-pyrazoles commonly known as 2-pyrazolines. The present review is a concerted effort to retrace compounds covered from 2009-till date which owe diverse biological activities to the 2-pyrazoline scaffold and also condenses the retro-synthetic approaches employed for their synthesis. This endeavor culminated in revelation that inhibitory potential varied when the substituents in particular N-substituents of 2-pyrazolines were altered.

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Section: Antimicrobial Activitymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

4,5-Dihydro-1H-pyrazole: an indispensable scaffold

Alex

Kumar

2013

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…The correlation equations for CH 3(keto) , H 4 , H 4 ′, H 5 , CH 2 , OCH 3 and CH 3(ester) proton chemical shifts (δ, ppm) are given in equations (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22). …”

Section: Spectral Correlationsmentioning

confidence: 99%

“…Many solvent assisted and solvent-free methods including cyclization [15,16], N-acetylation, N-thio-acetylation [17], Nphenylation [15], N-thio-amination [12,13] and condensation [14] were reported in the literature for synthesis of these pyrazoline derivatives. The catalysts such as, Lewis acids, weak acids [18], polyacids [19], sodium acetate [20], clays [21], fly-ash:H 2 SO 4 [14], SiO 2 -H 3 PO 4 [22], preheated fly-ash [12], fly-ash:PTS [13], with or without microwave and ultrasound irradiation [23] were utilized for the above reactions. Now-a-days chemists and organic researchers have paid more attention to solvent-free methods.…”

Section: Introductionmentioning

confidence: 99%

“…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.…”

Section: Introductionmentioning

confidence: 99%

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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

Self Cite

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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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Novel Pyrazoline‐based Organometallic Compounds Containing Ferrocenyl and Quinoline units: Synthesis, Characterization and Microbial susceptibilities

Parveen

Alatawi

Alsharif

et al. 2018

Applied Organom Chemis

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Some novel pyrazoline-based organometallic compounds were synthesized as new leads in antimicrobial chemotherapy. The structures of compounds were elucidated by different spectroscopic techniques and elemental analyses. All compounds were investigated for in vitro antimicrobial studies against fifteen ATTC bacterial and fungal strains. The microbial susceptibility of these compounds revealed that all the tested compounds gave good minimum inhibitory concentration (MIC) values against the tested organisms that are either similar or even better than the reference drugs amoxicillin and fluconazole, which gave MIC values 8-64 μg/ml against bacterial and 64 μg/ml against fungal strains, respectively. Among all compounds, compound (4d) 1-(5-(4-chlorophenyl)-3-ferrocenyl-4,5-dihydropyrazol-1-yl)-2-quinolin-8-yloxy) ethanone, emerged out the most promising antimicrobial organometallic derivative with MIC values against all the strains ranging from 8-32 μg/ml. Other compounds gave a range of MIC values between 16-64 μg/ml against S. bovis, 16-32 μg/ml against E. coli, and C. tropicalis except compound (4d) which gave MIC 8 μg/ml against S. bovis and E. coli, whereas 32 μg/ml against C. tropicalis.Collectively, these compounds gave a lower MIC value between 32-64 μg/ml against both of the biofilm forming strains namely, P. aeruginosa and S. mutans. The results of microbial susceptibility concluded that these novel organometallic compounds are new leads in antimicrobial chemotherapy and can be very useful for further optimization work on microbial chemotherapy. KEYWORDSantibacterial studies, antifungal studies, ferrocenyl and quinoline units, new leads in microbial chemotherapy, novel pyrazoline-based organometallics

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Synthesis, spectral studies and antimicrobial activities of some 2-naphthyl pyrazoline derivatives

Cited by 68 publications

References 23 publications

4,5-Dihydro-1H-pyrazole: an indispensable scaffold

4,5-Dihydro-1H-pyrazole: an indispensable scaffold

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

Novel Pyrazoline‐based Organometallic Compounds Containing Ferrocenyl and Quinoline units: Synthesis, Characterization and Microbial susceptibilities

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