Synthesis and biological evaluation of cyclopenten-1-one Mannich base oxovanadium compound

Tian, Jun; Li, Dongliu; Zhai, Fengying; Wang, Xiaohong; Li, Rui

doi:10.1007/s00044-009-9260-2

Cited by 8 publications

(2 citation statements)

References 20 publications

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“…For example, methylcyclopentenone (MCP) is a safe food additive as well as a flavor and pharmaceutical intermediate (Tian et al 2010). Moreover, methylcyclopentane, which is produced by MCP as an intermediate product, has a high octane number and can be used as an additive for ethanol gasoline (Sacia et al 2015).…”

Section: Introductionmentioning

confidence: 99%

Improved yields of high value-added ketones in bio-oil from biomass fast pyrolysis employing ZnO-modified magnesium aluminum spinel catalys

Yao

Zhao

et al. 2022

BioRes

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Ketones are an important class of multi-purpose products used for the production of high value-added chemicals. Herein, a novel method for the generation of methylcyclopentenone and pyridone via the modification of a magnesium aluminum spinel catalyst is proposed. In this study, zinc oxide, magnesium aluminum spinel, and ZnO-loaded magnesium aluminum spinel were used as catalysts for the catalytic pyrolysis of rape straw, corn stalk, and camphorwood powder at different reaction temperatures. Experimental results showed that different experimental temperatures and catalyst types played a crucial role in the formation of methylcyclopentenone and pyridone. Catalytic pyrolysis of rape straw with ZnO-loaded magnesium aluminum spinel increased the yield of methylcyclopentenone by greater than 6-fold compared to the yield without the catalyst, and the catalytic pyrolysis of corn stover increased the production of pyridone to 12.4%. The increase was primarily attributed to the conversion of cellulose and hemicellulose to ketones promoted by the ZnO-loaded magnesium aluminum spinel. These findings demonstrated that ZnO-loaded magnesium aluminum spinel catalysts can provide a new approach for enhancing the yield of methylcyclopentenone and pyridone during biomass fast pyrolysis.

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Section: Introductionmentioning

confidence: 99%

Improved yields of high value-added ketones in bio-oil from biomass fast pyrolysis employing ZnO-modified magnesium aluminum spinel catalys

Yao

Zhao

et al. 2022

BioRes

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“…The biological and pharmacological effects of vanadium element include coordination capability and chemical similarity between vanadate and phosphate. 2 Some inorganic vanadates show insulin-mimetic properties, as well as antitumor activities. A number of vanadium complexes with various types of organic ligands are reported to possess interesting antidiabetic activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, X-Ray Crystal Structures and Antibacterial Activities of Oxidovanadium(V) Complexes with Hydrazone and Hydroxamate Ligands

Qian

2019

ACSi

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Two new oxidovanadium(V) complexes, [VOL 1 L] (1) and [VOL 2 L]•CH 3 OH (2•CH 3 OH), where L 1 and L 2 are the dianionic form of N'-(3-bromo-2-hydroxybenzylidene)picolinohydrazide (H 2 L 1) and 2-chloro-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide (H 2 L 2), respectively, and L is the monoanionic form of 2-hydroxybenzohydroxamic acid (HL), were prepared and characterized by elemental analysis, infrared and electronic spectroscopy. Structures of the complexes were further confirmed by single crystal X-ray determination. The V atoms in the complexes are in octahedral coordination. The hydrazone ligands coordinate to the V atoms through the phenolate O, imino N, and enolate O atoms. The hydroxamate ligand coordinates to the V atom through the carbonyl and hydroxy O atoms. The complexes show effective antibacterial activity against B. subtilis, S. aureus and E. coli. The presence of Cl substitute group in the complex may enhance the antibacterial activity.

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Ab initio calculations of molecular properties of low–lying electronic states of 2–cyclopenten–1–one – link with biological activity

2012

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Geometries, vibrational frequencies, vertical and adiabatic excitation energies, dipole moments and dipole polarizabilities of the ground and the three lowest electronic excited states, S₁(n, π*), T₁(n, π*), and T₂(π, π*) of the 2-cyclopenten-1-one molecule (2CP) were calculated at the CCSD and CCSD(T) levels of approximation. Our results indicate that two triplets T₁(n, π*) and T₂(π, π*) are lying very close each to other, while the singlet S₁(n, π*) is well above them. There are dramatic changes in dipole moments for (n, π*) excited states in respect to the ground state. On the other hand the T₂(π, π*) state has a similar dipole moment as the ground state. These changes can be interpreted within the MO picture using electrostatic potential maps and changes in model IR spectra. Our CCSD(T) dipole moment data for the ground state and almost isoenergetic triplets T₁(n, π*) and T₂(π, π*) are 1.469 a.u., 0.551 a.u., and 1.124 a.u., respectively. Dipole polarizabilities of investigated excited states are much less affected by electron excitations than dipole moments. These are the first dipole moment and polarizability data of 2CP in the literature. The changes of molecular properties upon excitation to S₁(n, π*) and T₁(n, π*) correlate with the experimental data on the biological activity of 2CP related to the α, β-unsaturated carbonyl group.

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Synthesis and biological evaluation of cyclopenten-1-one Mannich base oxovanadium compound

Cited by 8 publications

References 20 publications

Improved yields of high value-added ketones in bio-oil from biomass fast pyrolysis employing ZnO-modified magnesium aluminum spinel catalys

Improved yields of high value-added ketones in bio-oil from biomass fast pyrolysis employing ZnO-modified magnesium aluminum spinel catalys

Synthesis, Characterization, X-Ray Crystal Structures and Antibacterial Activities of Oxidovanadium(V) Complexes with Hydrazone and Hydroxamate Ligands

Ab initio calculations of molecular properties of low–lying electronic states of 2–cyclopenten–1–one – link with biological activity

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