Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
1
pubmed:dateCreated
2006-1-17
pubmed:abstractText
The antioxidant properties of Hantzsch 1,4-dihydropyridine esters and two dibenzo-1,4-dihydropyridines, 9,10-dihydroacridine (DHAC) and N-methyl-9,10-dihydroacridine (N-Me-DHAC), have been explored by determining whether they retard the autoxidation of styrene or cumene at 30 degrees C. Despite a claim to the contrary [(2003) Chem. Res. Toxicol. 16, 208-215], the Hantsch esters were found to be virtually inactive as chain-breaking antioxidants (CBAs), their reactivity toward peroxyl radicals being some 5 orders of magnitude lower than that of the excellent CBA, 2,2,5,7,8-pentamethyl-6-hydroxy-chroman (PMHC). DHAC was found to be about a factor of 10 less reactive than PMHC. From kinetic measurements using DHAC, N-deuterio-DHAC, and N-Me-DHAC, it is concluded that it is the N--H hydrogen in DHAC that is abstracted by peroxyl radicals, despite the fact that in DHAC the calculated C-H bond dissociation enthalpy (BDE) is about 11 kcal/mol lower than the N-H BDE. The rates of hydrogen atom abstraction by the 2,2-diphenyl-1-picrylhydrazyl radical (dpph*) have also been determined for the same series of compounds. The trends in the peroxyl and dpph* rate constants are similar.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
http://linkedlifedata.com/resource/pubmed/chemical/1,4-dihydropyridine, http://linkedlifedata.com/resource/pubmed/chemical/10-methyl-9,10-dihydroacridine, http://linkedlifedata.com/resource/pubmed/chemical/2,2,5,7,8-pentamethyl-6-hydroxychrom..., http://linkedlifedata.com/resource/pubmed/chemical/2,2-diphenyl-1-picrylhydrazyl, http://linkedlifedata.com/resource/pubmed/chemical/Acridines, http://linkedlifedata.com/resource/pubmed/chemical/Antioxidants, http://linkedlifedata.com/resource/pubmed/chemical/Benzene Derivatives, http://linkedlifedata.com/resource/pubmed/chemical/Biphenyl Compounds, http://linkedlifedata.com/resource/pubmed/chemical/Calcium Channel Blockers, http://linkedlifedata.com/resource/pubmed/chemical/Calcium Channels, L-Type, http://linkedlifedata.com/resource/pubmed/chemical/Chromans, http://linkedlifedata.com/resource/pubmed/chemical/Dihydropyridines, http://linkedlifedata.com/resource/pubmed/chemical/Free Radicals, http://linkedlifedata.com/resource/pubmed/chemical/Hydrazines, http://linkedlifedata.com/resource/pubmed/chemical/Nifedipine, http://linkedlifedata.com/resource/pubmed/chemical/Nimodipine, http://linkedlifedata.com/resource/pubmed/chemical/Peroxides, http://linkedlifedata.com/resource/pubmed/chemical/Picrates, http://linkedlifedata.com/resource/pubmed/chemical/Styrene, http://linkedlifedata.com/resource/pubmed/chemical/cumene, http://linkedlifedata.com/resource/pubmed/chemical/perhydroxyl radical
pubmed:status
MEDLINE
pubmed:month
Jan
pubmed:issn
0893-228X
pubmed:author
pubmed:issnType
Print
pubmed:volume
19
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
79-85
pubmed:dateRevised
2009-11-19
pubmed:meshHeading
pubmed:year
2006
pubmed:articleTitle
The L-type calcium channel blockers, hantzsch 1,4-dihydropyridines, are not peroxyl radical-trapping, chain-breaking antioxidants.
pubmed:affiliation
Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands, Department of Chemistry, Warsaw University, Pasteur 1, 02-093 Warsaw, Poland. peter.mulder@nrc.ca
pubmed:publicationType
Journal Article, Comparative Study, Research Support, Non-U.S. Gov't