1-Indanone chalcones and their 2,4-Dinitrophenylhydrazone derivatives: Synthesis, physicochemical properties and in vitro antibacterial activity

Fadare, Olatomide A.; Akinpelu, David A.; Ejemubu, Henry; Obafemi, Craig A.

doi:10.5897/ajpac2014.0558

Cited by 8 publications

(1 citation statement)

References 45 publications

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“…A 2,4-dinitrophenylhydrazone derivative of 1-indanone with a potent antimicrobial activity has been synthesized in 2014 by Obafemi et al utilizing unsubstituted 1-indanone as a starting material [125]. This bioactive derivative has been obtained by Claisen–Schmidt reaction of 1-indanone with benzaldehyde, followed by condensation with 2,4-dinitrophenylhydrazine (DNP).…”

Section: Reviewmentioning

confidence: 99%

Synthesis of 1-indanones with a broad range of biological activity

Turek¹,

Szczęsna²,

Koprowski³

et al. 2017

Beilstein J. Org. Chem.

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This comprehensive review describes methods for the preparation of 1-indanones published in original and patent literature from 1926 to 2017. More than 100 synthetic methods utilizing carboxylic acids, esters, diesters, acid chlorides, ketones, alkynes, alcohols etc. as starting materials, have been performed. This review also covers the most important studies on the biological activity of 1-indanones and their derivatives which are potent antiviral, anti-inflammatory, analgesic, antimalarial, antibacterial and anticancer compounds. Moreover, they can be used in the treatment of neurodegenerative diseases and as effective insecticides, fungicides and herbicides.

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Section: Reviewmentioning

confidence: 99%

Synthesis of 1-indanones with a broad range of biological activity

Turek¹,

Szczęsna²,

Koprowski³

et al. 2017

Beilstein J. Org. Chem.

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Experimental and theoretical exploration on single crystal, structural, and quantum chemical parameters of (E)‐7‐(arylidene)‐1,2,6,7‐tetrahydro‐8H‐indeno[5,4‐b]furan‐8‐one derivatives: A comparative study

Adole¹,

Jagdale²,

Pawar³

et al. 2020

J Chinese Chemical Soc

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In the present research work, biologically important halogen-substituted (E)-7-(arylidene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one derivatives are studied from a structural investigation point of view. For a detailed molecular structure description, some quantum-chemical calculations were performed by using the density functional theory method with a basis set 6-311++G(d,p). The optimized molecular geometry, bond length, atomic charges, bond angle, and harmonic vibrational frequencies have been investigated. The quantum and structural entities such as total energy, electron density distribution in highest occupied molecular orbital and lowest unoccupied molecular orbital, charge distribution, electronegativity, absolute hardness (η), softness, electrophilicity, chemical potential, and charge transfer in molecules (ΔN max) have been computed using 6-311++G(d,p) basis set. Importantly, single-crystal analysis study for (E)-7-(2-chlorobenzylidene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b] furan-8-one (CBIF) has been presented. The single-crystal examination reveals CBIF has triclinic crystal lattice with nonclassical intermolecular short contact interactions. The vibrational wavenumbers are calculated and the scaled values are compared with the experimental FT-IR spectrum. Furthermore, the molecular electrostatic potential (MEP) and some thermodynamic functions were also explored using computational work. The theoretical geometrical parameters have been compared with the experimental results obtained from the single-crystal examination.

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Unexpected Simple and Catalyst‐Free Condensation Reaction of Spiro Dihydrofurans with 2,4‐Dinitrophenylhydrazine, Thiosemicarbazide, and Hydroxylamine for the Synthesis of Novel Corresponding 4,4,6′,6′‐Tetramethyl‐3′‐aryl‐3′,5′,6′,7′‐tetrahydrospiro[cyclohexane‐1,2′‐indole]‐4′,6(1′H)‐diones: Crystal Structure

Zhian

Pesyan

Aalinejad

et al. 2018

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).The reaction of 4 0 ,4 0 ,6,6-tetramethyl-3-aryl-3,5,6,7-tetrahydro-4H-spiro[benzofuran-2,1 0 -cyclohexane]-2 0 ,4,6 0 -trione with 2,4-dinitrophenylhydrazine, thiosemicarbazone, and hydroxylamine afforded unexpectedly novel corresponding 4,4,6 0 ,6 0 -tetramethyl-3 0 -aryl-3 0 ,5 0 ,6 0 ,7 0 -tetrahydrospiro[cyclohexane-1,2 0 -indole]-4 0 , 6(1 0 H)-diones in ethylene glycol in reflux and catalyst-free condition. The structure is characterized using FT-IR, 1 H, 13 C NMR, elemental analysis, mass spectrometer, and X-ray crystallography techniques.

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1-Indanone chalcones and their 2,4-Dinitrophenylhydrazone derivatives: Synthesis, physicochemical properties and in vitro antibacterial activity

Cited by 8 publications

References 45 publications

Synthesis of 1-indanones with a broad range of biological activity

Synthesis of 1-indanones with a broad range of biological activity

Experimental and theoretical exploration on single crystal, structural, and quantum chemical parameters of (E)‐7‐(arylidene)‐1,2,6,7‐tetrahydro‐8H‐indeno[5,4‐b]furan‐8‐one derivatives: A comparative study

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