Synthesis, antioxidant and antimicrobial activity of novel vanillin derived piperidin-4-one oxime esters: Preponderant role of the phenyl ester substituents on the piperidin-4-one oxime core

Harini, Salakatte Thammaiah; Kumar, Hemant; Rangaswamy, Javarappa; Naik, Nagaraja

doi:10.1016/j.bmcl.2012.10.019

Cited by 77 publications

(44 citation statements)

References 20 publications

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“…On the basis of the promising initial data and also due to our interests in synthesis of biologically active heterocycles [8][9][10][11] , here a library of novel analogues was synthesized. Along with identifying the structural parameters that govern the antioxidant and antibacterial properties.…”

Section: Figure 1 General Structure Of Bioactive Quinazolinesmentioning

confidence: 99%

Novel Phenyl and Purine Substituted Derivatives of Quinazolinones: Synthesis, Antioxidant and Antibacterial Features

2018

Chem Sci Trans

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A one-pot three-component protocol for the preparation of novel phenyl and purine substituted derivatives of quinazolinones through the reaction of 7H-purin-6-amine, cyclohexane-1,3-diketone and aromatic aldehydes in acetic acid is reported. A broad range of quinazolinones were obtained in 55−82% overall yield. In this article, we describe the identification of the good oxidation inhibitors (IC 50 values of 13, 16, 22 and 25 µM, respectively). Compounds IVf and IVg exhibited excellent in vitro radical inhibition activity against a DPPH radical, providing new opportunities for the series. In vitro antibacterial activity toward bacterial strain was also examined, compounds IVb, IVc and IVi exhibits stronger bacterial activity. Overall, the obtained results suggest that further optimization of activity of the series could provide a strong lead for a new antioxidant and antibacterial drug development program.

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Section: Figure 1 General Structure Of Bioactive Quinazolinesmentioning

confidence: 99%

Novel Phenyl and Purine Substituted Derivatives of Quinazolinones: Synthesis, Antioxidant and Antibacterial Features

2018

Chem Sci Trans

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“…Significant secondary bonding interactions are also frequently observed in these derivatives, as a result of M─X σ* antibonding orbital which has the potential to act as an acceptor orbital towards another donor atom . Antimony derivatives are more valuable from the medicinal chemistry point of view and in drug designing as different oximes and their metal derivatives are found to be important and exhibit significant bioactivity in chelating therapeutic drugs, as inhibitors of enzymes and as intermediates in biosynthesis of nitrogen oxides, and have antimicrobial, anticancer, fungicidal, bactericidal and antioxidant activities. In addition, dithiocarbamate derivatives with various metals have also been extensively studied because of their biological activities and use in analytical chemistry and as medicines as antidotes and antioxidants .…”

Section: Introductionmentioning

confidence: 99%

Syntheses, characterization, antibacterial activity and molecular modelling of phenylantimony(III) heteroleptic derivatives containing substituted oximes and piperidine dithiocarbamate

Beniwal

Chhimpa

Gaur

et al. 2017

Applied Organom Chemis

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Six new heteroleptic phenylantimony(III) derivatives containing substituted oximes and dithiocarbamate moieties of the type (where R = ─C 6 H 5 , X = ─CH 3 (2a); R = ─C 6 H 4 CH 3 , X = ─CH 3 (2b); R = ─C 6 H 4 Cl, X = ─CH 3 (2c); R = ─C 6 H 4 Br, X = ─CH 3 (2d); R = ─C 6 H 4 OH, X = ─H (2e); R(X)C = (2f)) have been synthesized by the reactions of phenylantimony(III) dichloride with the sodium salt of substituted oximes and dithiocarbamate moiety in unimolar ratio with stirring in dichloromethane. All these newly synthesized derivatives have been characterized using physicochemical and elemental analyses. Structures have been proposed on the basis of infrared, 1 H NMR, 13 C NMR and LC-MS spectral studies and molecular modelling. In these derivatives the oxime behaves in an unidentate manner whereas dithiocarbamate behaves in a monofunctional anisobidentate manner. Pseudo-trigonal bipyramidal (ψ-TBP) geometry around the antimony metal centre is proposed for these phenylantimony(III) heteroleptic derivatives. The geometry of a representative complex has been optimized through molecular modelling. These newly synthesized derivatives were screened against Bacillus subtilis (Gram-positive) and Escherichia coli (Gram-negative) bacteria to evaluate their antibacterial potential. The structureactivity relationship for antibacterial activity among the four derivatives 2a, 2c, 2e and 2f is discussed.

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“…Their derivatives are used for the prevention and treatment of cardiovascular disease (Jeong et al, 2013(Jeong et al, , 2006. These compounds are good antioxidants and are used in pharmaceutical compositions for their anti-microbial activity (Liu et al, 2008;Harini et al, 2012;Ahluwalia et al, 2017). In view of this interest, we have synthesized the title oxime ester derivative and report herein on its crystal structure.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of (E)-furan-2-carbaldehydeO-benzoyloxime

2017

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In the title compound, C 12 H 9 NO 3 , the benzoate and furan rings are almost coplanar, making a dihedral angle of 11.68 (9) . The twist angle between the -COO group and the benzene ring is only 2.79 (16) . In the crystal, molecules are linked by C-HÁ Á ÁO hydrogen bonds, forming chains along [100]. The molecules stack in a herringbone fashion and inversion-related chains are linked by offset -interactions [intercentroid distance = 3.931 (1) Å ], forming ribbons propagating along the a-axis direction.

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Synthesis, antioxidant and antimicrobial activity of novel vanillin derived piperidin-4-one oxime esters: Preponderant role of the phenyl ester substituents on the piperidin-4-one oxime core

Cited by 77 publications

References 20 publications

Novel Phenyl and Purine Substituted Derivatives of Quinazolinones: Synthesis, Antioxidant and Antibacterial Features

Novel Phenyl and Purine Substituted Derivatives of Quinazolinones: Synthesis, Antioxidant and Antibacterial Features

Syntheses, characterization, antibacterial activity and molecular modelling of phenylantimony(III) heteroleptic derivatives containing substituted oximes and piperidine dithiocarbamate

Crystal structure of (E)-furan-2-carbaldehydeO-benzoyloxime

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