Linked Life Data

18322337

Source:http://linkedlifedata.com/resource/pubmed/id/18322337

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
Pt 3
pubmed:dateCreated
2008-3-6
pubmed:abstractText
Four neutral vinyl sulfones, two of which are paired with phosphonate groups, are described. The compounds are diisopropyl (2-phenylethenylsulfonylmethyl)phosphonate, C(15)H(23)O(5)PS, (I), diisopropyl {[2-(7-methoxy-1,3-benzodioxol-5-yl)ethenylsulfonyl]methylsulfonylmethyl}phosphonate, C(18)H(27)O(10)PS(2), (II), bis(trans-2-phenylethenyl) sulfone, C(16)H(14)O(2)S, (III), and bis(trans-2-phenylethenylsulfonyl)methane, C(17)H(16)O(4)S(2), (IV). Their structures can be considered as highly functionalized mimics of mono-, di- and triphosphates. These phosphate isosteres are currently of interest as agents for enzyme inhibition in both cancer and HIV therapy. All except one of the compounds has Z' > 1. The lone exception is (IV), a disulfone with twofold crystallographic symmetry. Geometrically, the sulfone functionality is found to be a good mimic for phosphate. The principal effect of the vinyl group is to shorten the S-C(vinyl) distance relative to the S-CH(2) distance by ca 0.05 A. The S-C-S and S-C-P backbones resemble the P-O-P backbone but are not identical because the S-C and P-C distances are longer than the P-O distance and the S-C-S and S-C-P angles are more acute than the P-O-P angle. No prior crystal structures of comparable compounds have been published.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Mar
pubmed:issn
1600-5759
pubmed:author
pubmed:issnType
Electronic
pubmed:volume
64
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
o132-6
pubmed:meshHeading
pubmed:year
2008
pubmed:articleTitle
Vinyl sulfones.
pubmed:affiliation
Department of Chemistry, University of California, One Shields Avenue, Davis, CA 95616, USA.
pubmed:publicationType
Journal Article, Research Support, U.S. Gov't, Non-P.H.S., Research Support, Non-U.S. Gov't