Linked Life Data

7359523

Source:http://linkedlifedata.com/resource/pubmed/id/7359523

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
1
pubmed:dateCreated
1980-5-14
pubmed:abstractText
5-(4-Chlorobenzoyl)-4-(hydroxymethyl)-1-methyl-1H-pyrrole-2-acetic acid (2), the major oxidative metabolite of zomepirac (1), was synthesized starting with ethyl 5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetate (3), the ethyl ester of 1. Compound 3 was oxidized with selenium dioxide to afford the alpha-oxoester, 5. Bromination of 5 with N-bromosuccinimide produced bromomethylpyrrole 7, and reaction of 7 with acetate produced by corresponding acetoxymethylpyrrole 8. Hydrogen sulfide effected the selective reduction of the side-chain carbonyl group if 8 to give 9. Saponification of 9 gave the title compound, 2. Synthetic 2 was identical with the isolated metabolite of zomepirac (1). Biological testing revealed that the metabolite was essentially devoid of the biological activity associated with zomepirac.
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
23
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
98-100
pubmed:dateRevised
2006-11-15
pubmed:meshHeading
pubmed:year
1980
pubmed:articleTitle
Synthesis and biological activity of 5-(4-chlorobenzoyl)-4-(hydroxymethyl)-1-methyl-1H-pyrrole-2-acetic acid, a major metabolite of zomepirac sodium.
pubmed:publicationType
Journal Article, In Vitro