Vinyl sulfones

Jessica H. Wong, Marilyn M. Olmstead, James C. Fettinger, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Four neutral vinyl sulfones, two of which are paired with phosphonate groups, are described. The compounds are diisopropyl (2-phenyl-ethenylsulfonyl- meth-yl)phosphonate, C15H23O5PS, (I), diisopropyl {[2-(7-meth-oxy-1,3-benzodi- oxol-5-yl)ethenylsulfon-yl]methyl-sulfonyl-meth-yl}-phos-phon-ate, C18H27O10PS2, (II), bis-(trans-2-phenyl-ethen-yl) sulfone, C16H14O2S, (III), and bis-(trans-2-phenyl-ethenylsulfon-yl)-methane, C17H16O4S2, (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 - CH2 distance by ca 0.05 Å. 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.

Original languageEnglish (US)
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume64
Issue number3
DOIs
StatePublished - 2008

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Structural Biology

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