Synthesis and Cytotoxic Evaluation of Some 6-Arylidene-2-(α-hydroxyamino-α-arylmethyl)cyclohexanone Oximes and Related Compounds

Dimmock, Jonathan R.; Sidhu, K. K.; Quail, J. Wilson; Jia, Z.; Duffy, Michael J.; Reid, R. S.; Kirkpatrick, David; Zhu, Liping; Fletcher, S.M.

doi:10.1002/jps.2600811103

Cited by 8 publications

(2 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The enhancement of pharmacological potency of PDE IV as an anti-TNF-¬ inhibitor was demonstrated by combination of compound 6 with wellknown TNF-¬ inhibitors (Figure 3). In addition, oxime (ketone) functionality may be more enforced in tumour cells, which have low pH, because, under this condition, functional ketones can be selectively released in tumour cells (Dimmock et al 1992). The potential significance of compound 6 in anti-cancer therapy should now be carefully evaluated.…”

Section: Discussionmentioning

confidence: 99%

Effects of dialkoxylphenyl compounds with oxime group on macrophage function and the proliferation of lymphocytes

Yoo

Son

Park

et al. 2004

Journal of Pharmacy and Pharmacology

View full text Add to dashboard Cite

Dialkoxyphenyl compounds have been reported to possess anti-inflammatory activity through inhibition of phosphodieseterase (PDE) type IV. In this study, a series of derivatives of dialkoxyphenyl compounds with an oxime group, which is generally known to be one of the biologically active functional groups, were prepared and evaluated for their ability to inhibit the production of inflammatory mediators in activated macrophages and the proliferation of lymphocytes. The structure-activity relationship (SAR) study with 12 compounds on tumour necrosis factor (TNF)-alpha inhibition, analysed by the oxime geometry and different size of spacers between the oxime and phenyl group, indicated that there might be at least three possible hydrogen bonding sites in the inhibitor binding pocket of PDE IV. Of them, compound 6 clearly displayed the highest inhibitory effect on in-vitro TNF-alpha production from lipopolysaccharide (LPS)-stimulated RAW264.7 cells. Compound 6 also suppressed in-vivo TNF-alpha release from LPS-primed mice, a level comparable with that of the standard PDE IV inhibitor, rolipram. In addition, oxime compounds also significantly inhibited both nitric oxide production from activated RAW264.7 cells and T lymphocyte proliferation elicited by concanavalin A but not IL-2. The data suggest that the oxime group may act as a functional group, capable of interacting with the inhibitor-binding pocket of target PDE IV. Therefore, it is conceivable that compound 6 may have the potential either to be developed as a new anti-inflammatory drug or to be used to develop more potent analogues.

show abstract

Section: Discussionmentioning

confidence: 99%

Effects of dialkoxylphenyl compounds with oxime group on macrophage function and the proliferation of lymphocytes

Yoo

Son

Park

et al. 2004

Journal of Pharmacy and Pharmacology

View full text Add to dashboard Cite

show abstract

“…Chalcones and their analogues are either found in plants or obtained from specific synthetic pathways and have shown numerous applications as liquid crystal materials, pH sensors, , nonlinear optical materials, , as well as their remarkable biological properties: antitumor, , anti-inflammatory, antifungal, − antibacterial, ,, and antioxidant. − Some of these properties can be related to fuel applications, such as energy efficiency or additives, − and often fuels such as ethanol and biofuels are prone to suffer from degradation and oxidation problems, mainly caused by micro-organisms − or even the lower combustion capacity, therefore, a lower energy efficiency. − …”

Section: Introductionmentioning

confidence: 99%

Cyclohexanone-Based Chalcones as Alternatives for Fuel Additives

et al. 2022

View full text Add to dashboard Cite

The use of small molecules, such as chalcones and their derivatives, for more efficient fuels is in increasing demand due to environmental factors. Here, three crystal structures (BH I , II , and III ) of cyclohexanone-based chalcones were synthesized and described by single-crystal X-ray diffraction and Hirshfeld surface analysis. The supramolecular modeling analysis on the hyperconjugative interaction energies and QTAIM analysis at the ωB97XD/6-311++G(d,p) level of theory were carried out to analyze the intermolecular interactions in the solid-state. The structure–property relationship, frontier molecular orbital, molecular electrostatic potential, and the experimental calorific value analysis show that the three compounds are a good alternative to be used as an additive for some fuels. Our findings represent a further step forward in the development of cheaper and more efficient fuel additives and pose an opportunity for further investigation on similar analogues.

show abstract

ChemInform Abstract: Synthesis and Cytotoxic Evaluation of Some 6‐Arylidene‐2‐(α‐ hydroxyamino‐α‐arylmethyl)cyclohexanone Oximes and Related Compounds.

et al. 1995

View full text Add to dashboard Cite

show abstract

Synthesis and Cytotoxic Evaluation of Some 6-Arylidene-2-(α-hydroxyamino-α-arylmethyl)cyclohexanone Oximes and Related Compounds

Cited by 8 publications

References 12 publications

Effects of dialkoxylphenyl compounds with oxime group on macrophage function and the proliferation of lymphocytes

Effects of dialkoxylphenyl compounds with oxime group on macrophage function and the proliferation of lymphocytes

Cyclohexanone-Based Chalcones as Alternatives for Fuel Additives

ChemInform Abstract: Synthesis and Cytotoxic Evaluation of Some 6‐Arylidene‐2‐(α‐ hydroxyamino‐α‐arylmethyl)cyclohexanone Oximes and Related Compounds.

Contact Info

Product

Resources

About