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| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
2
|
| pubmed:dateCreated |
1989-8-18
|
| pubmed:abstractText |
3-H-1-Carbacephem nuclei with or without a 2 alpha- or 2 beta-methyl group were prepared via 2 + 2 cycloaddition followed by intramolecular Horner-Emmons cyclization. Optically active 3-H-1-carbacephem compounds were efficiently prepared by employing a penicillin acylase-producing microorganism in two ways. That is, the 7-phenylacetamide of a racemic carbacephem nucleus was hydrolyzed enantioselectively with the enzyme to afford the optically pure nucleus, which was then acylated to give antimicrobial compounds. Alternatively, a racemic carbacephem nucleus was directly and enantioselectively phenylglycylated with the enzyme. 3-H-1-Carbacephem nuclei appeared to be better substrates for penicillin acylase than penam or cephem nuclei of natural origin. 3-H-1-Carbacephem compounds showed potent antimicrobial activity; compound 32a exhibited activity comparable to that of ceftizoxime, a cephem analog with the same acyl group. It is of interest that the 3-H-1-carbacephem compound turned out to have more potent antimicrobial activity than its 3-substituted methyl analog.
|
| pubmed:language |
eng
|
| pubmed:journal | |
| pubmed:citationSubset |
IM
|
| pubmed:chemical | |
| pubmed:status |
MEDLINE
|
| pubmed:month |
Feb
|
| pubmed:issn |
0009-2363
|
| pubmed:author | |
| pubmed:issnType |
Print
|
| pubmed:volume |
37
|
| pubmed:owner |
NLM
|
| pubmed:authorsComplete |
Y
|
| pubmed:pagination |
315-21
|
| pubmed:dateRevised |
2008-11-21
|
| pubmed:meshHeading | |
| pubmed:year |
1989
|
| pubmed:articleTitle |
Synthesis and biological evaluation of optically active 3-H-1-carbacephem compounds.
|
| pubmed:publicationType |
Journal Article
|