Linked Life Data

6317861

Source:http://linkedlifedata.com/resource/pubmed/id/6317861

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
1
pubmed:dateCreated
1984-2-20
pubmed:abstractText
Two palladium-catalyzed carbon-carbon bond forming reactions were found to be useful for the modification of a protected amino acid derivative containing a sterically hindered isopropenyl group. Arylation of the terminal methylene group of the dimethyl ester of N-(ethoxycarbonyl)kainic acid (3) was accomplished by treatment with an aromatic amine, palladium(II) acetate, and tert-butyl nitrite. Substitution of the allylic methyl group of 3 was accomplished by conversion to the pi-(allyl)palladium complex (5) which, on subsequent treatment with the carbanions of tert-butyl acetoacetate or phenylthioacetone, gave the alkylated products. Both the (Z)- and (E)-3-nitrophenyl derivatives (8a,b) of kainic acid were active in the standard binding assay. Unexpectedly, the cis compound in the nitrophenyl series (8a), which more closely resembles the extended conjugation found in domoic acid, was found to be 20 times less potent than the trans derivative 8b. The latter had one-fifth the receptor-binding affinity of kainic acid.
pubmed:grant
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Jan
pubmed:issn
0022-2623
pubmed:author
pubmed:issnType
Print
pubmed:volume
27
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
52-6
pubmed:dateRevised
2008-11-21
pubmed:meshHeading
pubmed:year
1984
pubmed:articleTitle
Palladium (II)-catalyzed olefin-coupling reactions of kainic acid: effects of substitution on the isopropenyl group on receptor binding.
pubmed:publicationType
Journal Article, Research Support, U.S. Gov't, P.H.S., Research Support, Non-U.S. Gov't