PubMed Health⌕ Search
Home/Archive/PubMed

PubMed · 15911266

Quantitative structure-activity relationship studies for antioxidant hydroxybenzalacetones by quantum chemical- and 3-D-QSAR(CoMFA) analyses.

Chisako Yamagami·Miki Akamatsu·Noriko Motohashi·Shogo Hamada·Takao Tanahashi
View original source ↗Export metadata ↓

Abstract

Antioxidant activities for a series of hydroxybenzalacetones, OH-BZ, evaluated by their inhibitory potencies against lipid peroxidation induced by gamma-ray irradiation or t-BuOOH, were analyzed quantitatively using quantum-chemical parameters calculated by semi-empirical molecular orbital (MO) calculations. The energy of the highest occupied molecular orbital (E(HOMO)) and frontier electron densities (HOMO) on the phenolic oxygen atom (F(H,O)), together with the steric parameter (E(s)) for the substituent ortho to the phenolic oxygen, showed excellent correlations. We also performed 3D-QSAR studies by using the comparative molecular field analysis (CoMFA) model. The results were compared with the corresponding classical QSAR correlations.

Explore related subjects

AcetoneAntioxidantsQuantitative Structure-Activity RelationshipQuantum TheoryJournal ArticleResearch Support, Non-U.S. Gov't

Keep this discovery

Explore connections, maps & timelines

BibTeXRIS

Chisako Yamagami, Miki Akamatsu, Noriko Motohashi, Shogo Hamada, Takao Tanahashi. 2005-06-02. Quantitative structure-activity relationship studies for antioxidant hydroxybenzalacetones by quantum chemical- and 3-D-QSAR(CoMFA) analyses.. https://doi.org/10.1016/j.bmcl.2005.03.087

Cite the original work for its findings. Save a collection to share your selection of sources.

KEEP EXPLORING

Related citations

PubMed2007

The production of (R)-2-hydroxy-1-phenyl-propan-1-one derivatives by benzaldehyde lyase from Pseudomonas fluorescens in a continuously operated membrane reactor.

Benzaldehyde lyase (BAL; E.C. 4.1.2.38) from Pseudomonas fluorescens Biovar I catalyzes the reversible formation of benzoins from aromatic aldehydes, and, moreover, the coupling of aromatic with aliphatic aldehydes yielding derivatives of (R)-2-hydroxy-1-phenyl- propan-1-one (R)-HPPs), which are important chiral building blocks. In this paper, we report on the development of a reactor system that allows the selective production of substituted (R)-HPP-derivatives. The reaction systems yielding (R)-1-(3-chloro-phenyl)-2-hydroxy- propan-1-one, (R)-2-hydroxy-3-methoxy-1-(4-methoxy-phenyl)-propan-1-one, and (R)-2-hydroxy-3,3-dimethoxy-1-phenyl-propan-1-one were investigated. A kinetic model optimized by batch experiments was developed, for the description of both batch and continuously operated reactors. This model was used to describe the HPP production in a continuously operated enzyme membrane reactor. The reactor type used combines the advantages of high conversion and excellent selectivity with high space-time yields and total turnover numbers of up to ttn=43,000. Products were obtained in high yield on a gram scale.

Acetone↗
PubMed2007

Analysis of the inter-molecular interactions between amino acids and acetone by THz spectroscopy.

The THz spectra of amino acids after application of spots of acetone were measured. The 0.6 THz band was commonly observed in many amino acids that formed the intra-molecular salt structure. The band can be attributed to the interaction vibration from the common structural configuration of amino acids and acetone molecules. The evidence suggests that the vibration between the amino acids with intra-molecular salt structure and acetone has a peak at 0.6 THz. A model of the interaction vibration of acetone and the functional groups of amino acids is proposed.

Acetone↗
PubMed2007

Two-directional elaboration of hydroxyacetone under thermodynamically controlled conditions: allylation or 2-propynylation and aldol reaction.

Enolate generated from O-(tetrahydropyran-2-yl)hydroxyacetone under thermodynamically controlled conditions (1.3 equiv of NaH, THF, 0 degrees C to rt) was allylated at the carbon bearing the protected hydroxy group with very high regioselectively. When tert-BuOH, equivalent to the excessive portion of initially added NaH, was introduced into the mixture followed by addition of aldehyde, aldol reaction took place on the methyl group to give 1-substituted 4-hydroxy-(1E),6-heptadien-3-one in acceptable yields after acidic treatment of the mixture for dehydration and deprotection. Introducing a chiral auxiliary protecting group into hydroxyacetone led to asymmetric allylation though stereoselectivity was around 50% ee. Thus, the hidden aspect of the chemoselective nature of protected hydroxyacetone-derived enolate generated under thermodynamically controlled conditions has opened a new avenue for two-directional elaboration of hydroxyacetone that should be potentially useful in organic synthesis.

Acetone↗