Vinyl sulfones

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

Research output: Contribution to journalArticle

1 Citation (Scopus)

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

Fingerprint

Organophosphonates
Sulfones
sulfones
Phosphates
Enzyme inhibition
Diphosphates
Methane
phosphates
Crystal structure
HIV
diphosphates
human immunodeficiency virus
Enzymes
enzymes
therapy
Neoplasms
methane
cancer
crystal structure
divinyl sulfone

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Structural Biology

Cite this

Vinyl sulfones. / Wong, Jessica H.; Olmstead, Marilyn M.; Fettinger, James C.; Gervay-Hague, Jacquelyn.

In: Acta Crystallographica Section C: Crystal Structure Communications, Vol. 64, No. 3, 2008.

Research output: Contribution to journalArticle

Wong, Jessica H. ; Olmstead, Marilyn M. ; Fettinger, James C. ; Gervay-Hague, Jacquelyn. / Vinyl sulfones. In: Acta Crystallographica Section C: Crystal Structure Communications. 2008 ; Vol. 64, No. 3.
@article{cb530673eb464048a8a4cfda3ca63c83,
title = "Vinyl sulfones",
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 {\AA}. 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.",
author = "Wong, {Jessica H.} and Olmstead, {Marilyn M.} and Fettinger, {James C.} and Jacquelyn Gervay-Hague",
year = "2008",
doi = "10.1107/S0108270108002692",
language = "English (US)",
volume = "64",
journal = "Acta Crystallographica Section C: Crystal Structure Communications",
issn = "0108-2701",
publisher = "International Union of Crystallography",
number = "3",

}

TY - JOUR

T1 - Vinyl sulfones

AU - Wong, Jessica H.

AU - Olmstead, Marilyn M.

AU - Fettinger, James C.

AU - Gervay-Hague, Jacquelyn

PY - 2008

Y1 - 2008

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=40449096297&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=40449096297&partnerID=8YFLogxK

U2 - 10.1107/S0108270108002692

DO - 10.1107/S0108270108002692

M3 - Article

VL - 64

JO - Acta Crystallographica Section C: Crystal Structure Communications

JF - Acta Crystallographica Section C: Crystal Structure Communications

SN - 0108-2701

IS - 3

ER -