| pubmed-article:15588091 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:15588091 | lifeskim:mentions | umls-concept:C1704689 | lld:lifeskim |
| pubmed-article:15588091 | lifeskim:mentions | umls-concept:C0205103 | lld:lifeskim |
| pubmed-article:15588091 | lifeskim:mentions | umls-concept:C0038477 | lld:lifeskim |
| pubmed-article:15588091 | lifeskim:mentions | umls-concept:C1167622 | lld:lifeskim |
| pubmed-article:15588091 | lifeskim:mentions | umls-concept:C1373040 | lld:lifeskim |
| pubmed-article:15588091 | lifeskim:mentions | umls-concept:C0678594 | lld:lifeskim |
| pubmed-article:15588091 | pubmed:issue | 26 | lld:pubmed |
| pubmed-article:15588091 | pubmed:dateCreated | 2004-12-13 | lld:pubmed |
| pubmed-article:15588091 | pubmed:abstractText | The design and synthesis of a series of seven tricyclic 6-methylidene penems as novel class A and C serine beta-lactamase inhibitors is described. These compounds proved to be very potent inhibitors of the TEM-1 and AmpC beta-lactamases and less so against the class B metallo-beta-lactamase CcrA. In combination with piperacillin, their in vitro activities enhanced susceptibility of all class C resistant strains from various bacteria. Crystallographic structures of a serine-bound reaction intermediate of 17 with the class A SHV-1 and class C GC1 enzymes have been established to resolutions of 2.0 and 1.4 A, respectively, and refined to R-factors equal 0.163 and 0.145. In both beta-lactamases, a seven-membered 1,4-thiazepine ring has formed. The stereogenic C7 atom in the ring has the R configuration in the SHV-1 intermediate and has both R and S configurations in the GC1 intermediate. Hydrophobic stacking interactions between the tricyclic C7 substituent and a tyrosine side chain, rather than electrostatic or hydrogen bonding by the C3 carboxylic acid group, dominate in both complexes. The formation of the 1,4- thiazepine ring structures is proposed based on a 7-endo-trig cyclization. | lld:pubmed |
| pubmed-article:15588091 | pubmed:grant | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:15588091 | pubmed:language | eng | lld:pubmed |
| pubmed-article:15588091 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:15588091 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:15588091 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:15588091 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
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| pubmed-article:15588091 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:15588091 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:15588091 | pubmed:month | Dec | lld:pubmed |
| pubmed-article:15588091 | pubmed:issn | 0022-2623 | lld:pubmed |
| pubmed-article:15588091 | pubmed:author | pubmed-author:WeissWilliam... | lld:pubmed |
| pubmed-article:15588091 | pubmed:author | pubmed-author:NukagaMichiyo... | lld:pubmed |
| pubmed-article:15588091 | pubmed:author | pubmed-author:KnoxJames RJR | lld:pubmed |
| pubmed-article:15588091 | pubmed:author | pubmed-author:HujerAndrea... | lld:pubmed |
| pubmed-article:15588091 | pubmed:author | pubmed-author:BonomoRobert... | lld:pubmed |
| pubmed-article:15588091 | pubmed:author | pubmed-author:PetersenPeter... | lld:pubmed |
| pubmed-article:15588091 | pubmed:author | pubmed-author:AgarwalAtulA | lld:pubmed |
| pubmed-article:15588091 | pubmed:author | pubmed-author:YangYoujunY | lld:pubmed |
| pubmed-article:15588091 | pubmed:author | pubmed-author:MansourTarek... | lld:pubmed |
| pubmed-article:15588091 | pubmed:author | pubmed-author:GuYansongY | lld:pubmed |
| pubmed-article:15588091 | pubmed:author | pubmed-author:AbeTakaoT | lld:pubmed |
| pubmed-article:15588091 | pubmed:author | pubmed-author:VenkatesanAra... | lld:pubmed |
| pubmed-article:15588091 | pubmed:author | pubmed-author:Dos... | lld:pubmed |
| pubmed-article:15588091 | pubmed:issnType | Print | lld:pubmed |
| pubmed-article:15588091 | pubmed:day | 16 | lld:pubmed |
| pubmed-article:15588091 | pubmed:volume | 47 | lld:pubmed |
| pubmed-article:15588091 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:15588091 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:15588091 | pubmed:pagination | 6556-68 | lld:pubmed |
| pubmed-article:15588091 | pubmed:dateRevised | 2007-11-14 | lld:pubmed |
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| pubmed-article:15588091 | pubmed:year | 2004 | lld:pubmed |
| pubmed-article:15588091 | pubmed:articleTitle | Structure-activity relationship of 6-methylidene penems bearing tricyclic heterocycles as broad-spectrum beta-lactamase inhibitors: crystallographic structures show unexpected binding of 1,4-thiazepine intermediates. | lld:pubmed |
| pubmed-article:15588091 | pubmed:affiliation | Wyeth Research, 401 N. Middletown Road, Pearl River, New York 10965, USA. | lld:pubmed |
| pubmed-article:15588091 | pubmed:publicationType | Journal Article | lld:pubmed |
| pubmed-article:15588091 | pubmed:publicationType | Research Support, U.S. Gov't, P.H.S. | lld:pubmed |
| pubmed-article:15588091 | pubmed:publicationType | Research Support, U.S. Gov't, Non-P.H.S. | lld:pubmed |
| http://linkedlifedata.com/r... | http://linkedlifedata.com/r... | pubmed-article:15588091 | lld:chembl |
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