Synthesis, Spectral Correlations and Antimicrobial Activities of 2-Pyrimidine Schiff’s Bases

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

doi:10.56431/p-4w6n3u

Cited by 7 publications

(15 citation statements)

References 18 publications

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“…The results of statistical analysis [34][35][36][37] are shown in Table 2. From Table 2, it is evident that the UV absorption maximum λ max (nm) values of all the substituted (E)-1-benzylidene-2-(4chlorophenyl)hydrazines have shown poor correlations (r < 0.900) with Hammett substituent constants namely, σ, σ + , σ I, σ R and F and R parameters.…”

Section: Uv-visible Spectral Correlationsmentioning

confidence: 99%

“…The results of the statistical analysis [34][35][36][37] are presented in Table 2, it is evident that the infrared stretching frequency νC=N (cm -1 ) values of all the substituted (E)-1-benzylidene-2-(4chlorophenyl)hydrazines, except those with parent (H) and 3-NO 2 substituents have shown satisfactory correlations with Hammett constants namely, σ (r =0.905) and σ + (r =0.906). The infrared stretching frequency νC=N (cm -1 ) values of all the substituted (E)-1-benzylidene-2-(4-chlorophenyl)hydrazines, except those with 3-NO 2 substituent have shown satisfactory correlations with Hammett constant σ R (r =0.906) and Swain-Lupton R (r =0.907) parameters.…”

Section: Ir Spectral Correlationmentioning

confidence: 99%

“…The assigned chemical shift values (ppm) of all the substituted (E)-1-benzylidene-2-(4chlorophenyl)hydrazines are presented in Table 1. These CH=N (δ ppm) chemical shift values are correlated with different Hammett substituent constants and F and R parameters using single and multi-linear regression analyses [34][35][36][37]. In this correlation, the structure-parameter equation employed is shown in equation (7).…”

Section: Nmr Spectral Correlationmentioning

confidence: 99%

“…From the results of the statistical analysis [34][35][36][37] the 1 H NMR chemical shift δ CH =N (ppm) values of all the substituted (E)-1-benzylidene-2-(4-chlorophenyl)hydrazines have shown poor correlations (r < 0.900) with different Hammett constants and Swain-Lupton's F and R parameters. The failure in correlation is due to the reason that has been stated earlier.…”

Section: H Nmr Spectral Correlationmentioning

confidence: 99%

“…The results of the statistical analysis [34][35][36][37] are presented in chlorophenyl)hydrazines have shown poor correlations (r < 0.900) with different Hammett constants and Swain-Lupton's F and R parameters. The failure in correlation is due to the reason that has been stated earlier with resonance conjugative structure as shown in Fig.…”

Section: C Nmr Spectral Correlationmentioning

confidence: 99%

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Synthesis, Hammett Spectral Correlations and Antimicrobial Activities of (<i>E</i>)-1-Benzylidene-2-(4-Chlorophenyl)Hydrazines

Rajarajan¹,

Vijayakumar²,

Senbagam³

et al. 2015

ILCPA

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In the present study, a series of nine number of (E)-1-benzylidene-2-(4-chlorophenyl) hydrazine compounds have been synthesized by condensation reaction of meta and para substituted benzaldehydes with 4-chlorophenylhydrazine using acetic acid catalyst. They are characterized by their physical constants, UV (200-450 nm), Infra-Red (KBr, 4000-400 cm−1) and NMR (1H and 13C) spectral data. The observed UV, IR and NMR spectral data have been correlated with Hammett substituent constants and Swain-Lupton’s F and R parameters using single and multi-linear regression analysis. From the results of statistical analysis the effects of substituents on the spectral data have been discussed. The antimicrobial activities of all the synthesized (E)-1-benzylidene-2-(4-chlorophenyl) hydrazine compounds have been studied using Bauer–Kirby method.

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Section: Uv-visible Spectral Correlationsmentioning

confidence: 99%

Section: Ir Spectral Correlationmentioning

confidence: 99%

Section: Nmr Spectral Correlationmentioning

confidence: 99%

Section: H Nmr Spectral Correlationmentioning

confidence: 99%

Section: C Nmr Spectral Correlationmentioning

confidence: 99%

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Synthesis, Hammett Spectral Correlations and Antimicrobial Activities of (<i>E</i>)-1-Benzylidene-2-(4-Chlorophenyl)Hydrazines

Rajarajan¹,

Vijayakumar²,

Senbagam³

et al. 2015

ILCPA

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One‐Pot Three‐Component Synthesis of Some 6‐Methoxy‐2‐Naphthyl Pyrimidinones with Molecular Docking and Biological Activities Studies

Divya,

Gayathri,

Muthuvel

et al. 2024

ChemistrySelect

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A new series of 6‐methoxy‐2‐naphthalene based pyrimidinones were synthesized via one pot‐three component synthetic reaction of aryl aldehydes, 6‐methoxy‐2‐acetonapthone and urea in the presence of nano zinc ferrite catalyst under conventional method. The synthesized compounds were characterized by their spectral techniques including FT‐IR, H1, C13 NMR, LCMS, and analysis of elements. Molecular docking analysis was also performed to identify the protein‐ligand interactions and binding energy of synthesized compounds. Biological studies of all synthesized pyrimidinone compounds have been measured against bacterial and fungal strains by calculating the zone of inhibition.

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A Convenient and Practical Synthesis of Novel Pyrimidine Derivatives and its Therapeutic Potential

Arora,

Kumar,

Verma

2024

CBC

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Background:: A new series of 2-(2-(substituted aldehyde)hydrazinyl)-4-(2- chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile analogs (1–19) was prepared by using the Biginelli reaction. background: A novel series of 2-(2-(substituted aldehyde)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile analogues (1–19) was synthesized using the Biginelli reaction Methods:: TLC was employed to ensure the progress and confirmation of the reactions. Silica gel G was employed as the stationary phase, and mobile phases such as chloroform: toluene and acetone: n-hexane were used for the synthesized compounds. NMR has characterized the synthesized compound. MS IR, CHN. Results:: The prepared derivatives were evaluated in vitro for antimicrobial activity against various bacteria and fungi using the tube dilution technique. Notably, compounds 2-(2-(3-Ethoxy-4- hydroxybenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5- carbonitrile T1, 2-(2-(2-Hydroxybenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6- dihydropyrimidine-5 carbonitrile T6, and 2-(2-(4-Hydroxybenzylidene)hydrazinyl)-4-(2- chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile T16, displayed significant antibacterial activity, surpassing the standard drug Ampicillin. In the antifungal category, compounds 2-(2-(3-Ethoxy-4-hydroxybenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyri midine-5-carbonitrile T1, 2-(2-(3,4-Dimethoxybenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6- oxo-1,6-dihydropyrimidine-5-carbonitrile T2, and 2-(2-(2,4-Dichlorobenzylidene)hydrazinyl)-4-(2- chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile T13, were very much effective against both fungal strains A. niger as well as C. albicans. Furthermore, compounds 2-(2-(2- Hydroxybenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5 carbonitrile T6, 2-(2-(2-Nitrobenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyri midine-5-carbonitrile T8, 2-(2-(4-Chlorobenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo- 1,6-dihydropyrimidine-5-carbonitrile T12, and 2-(2-(4-Dimethylaminobenzylidene)hydrazinyl)-4-(2- chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile T14 demonstrated remarkable antioxidant properties, because of their low IC50 values in the DPPH assay. In the realm of anticancer activity, 2-(2-(substituted aldehyde)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6-dihydro pyrimidine-5-carbonitrile T9 outperformed the standard drug Adriamycin in terms of its effectiveness against human lung cancer cells (A-549) with a GI50 value of less than 10 according to the SRB assay. In addition, the antidiabetic assessment highlighted the excellent performance of compounds 2-(2- (2-Nitrobenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5- carbonitrile T8, 2-(2-(4-Chlorobenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6- dihydropyrimidine-5-carbonitrile T12, and 2-(2-(3-Nitrobenzylidene)hydrazinyl)-4-(2-chloro phenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile T15, with low IC50 values, when tested for their inhibition of α-amylase enzyme activity. Conclusions:: The synthesized derivatives demonstrated strong antimicrobial, antioxidant, anticancer, and antidiabetic properties when assessed using specific methods and compared to established drugs. Notably, compounds 2-(2-(3-Ethoxy-4-hydroxybenzylidene)hydrazinyl)-4-(2-chloro phenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile T1, 2-(2-(2-Hydroxybenzylidene) hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5 carbonitrile T6, and 2- (2-(2,4-Dichlorobenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine -5-carbonitrile T13, 2-(2-(4-Chlorobenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo- 1,6-dihydropyrimidine-5-carbonitrile T12 and 2-(2-(substituted aldehyde)hydrazinyl)-4-(2-chloro phenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile T9 exhibited even higher activity levels than the standard medications. The presence of electron-releasing groups in the synthesized compounds enhanced their antibacterial and antioxidant effects, particularly against B. subtilis. On the other hand, electron-withdrawing groups improved their anticancer and antidiabetic properties.

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Synthesis, Spectral Correlations and Antimicrobial Activities of 2-Pyrimidine Schiff’s Bases

Cited by 7 publications

References 18 publications

Synthesis, Hammett Spectral Correlations and Antimicrobial Activities of (<i>E</i>)-1-Benzylidene-2-(4-Chlorophenyl)Hydrazines

Synthesis, Hammett Spectral Correlations and Antimicrobial Activities of (<i>E</i>)-1-Benzylidene-2-(4-Chlorophenyl)Hydrazines

One‐Pot Three‐Component Synthesis of Some 6‐Methoxy‐2‐Naphthyl Pyrimidinones with Molecular Docking and Biological Activities Studies

A Convenient and Practical Synthesis of Novel Pyrimidine Derivatives and its Therapeutic Potential

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