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Solution-phase parallel Wittig olefination : Synthesis of substituted 1,2-diarylethanes

Husemoen, Gitte ; Olsson, Roger LU orcid ; Andersson, Carl Magnus ; Harvey, Scott C. and Hansen, Henrik C. LU (2003) In Journal of Combinatorial Chemistry 5(5). p.606-609
Abstract

An efficient strategy for solution-phase parallel synthesis of substituted 1,2-diarylethanes is described. A stilbene library was initially generated by Wittig olefination utilizing amino-labeled phosphines. The stilbene analogues were obtained in high yields and excellent purities after solid-phase extraction. Subsequent reduction of the stilbene libraries simultaneously unmasked functional groups by deprotection, facilitating orthogonal synthesis and further diversification into sublibraries. The libraries from libraries were obtained in good yields and purities using parallel solution-phase alkylation and acylation methodologies. Screening of the sublibraries revealed selective 5-HT2A inverse agonists with IC-50 values... (More)

An efficient strategy for solution-phase parallel synthesis of substituted 1,2-diarylethanes is described. A stilbene library was initially generated by Wittig olefination utilizing amino-labeled phosphines. The stilbene analogues were obtained in high yields and excellent purities after solid-phase extraction. Subsequent reduction of the stilbene libraries simultaneously unmasked functional groups by deprotection, facilitating orthogonal synthesis and further diversification into sublibraries. The libraries from libraries were obtained in good yields and purities using parallel solution-phase alkylation and acylation methodologies. Screening of the sublibraries revealed selective 5-HT2A inverse agonists with IC-50 values between 10 and 100 nM.

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author
; ; ; and
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Combinatorial Chemistry
volume
5
issue
5
pages
606 - 609
publisher
The American Chemical Society (ACS)
external identifiers
  • scopus:0141795489
ISSN
1520-4766
DOI
10.1021/cc0300210
language
English
LU publication?
no
id
272317ef-8c9c-466a-b1c3-d61e6ff6abd1
date added to LUP
2019-10-02 10:34:05
date last changed
2022-03-25 23:47:13
@article{272317ef-8c9c-466a-b1c3-d61e6ff6abd1,
  abstract     = {{<p>An efficient strategy for solution-phase parallel synthesis of substituted 1,2-diarylethanes is described. A stilbene library was initially generated by Wittig olefination utilizing amino-labeled phosphines. The stilbene analogues were obtained in high yields and excellent purities after solid-phase extraction. Subsequent reduction of the stilbene libraries simultaneously unmasked functional groups by deprotection, facilitating orthogonal synthesis and further diversification into sublibraries. The libraries from libraries were obtained in good yields and purities using parallel solution-phase alkylation and acylation methodologies. Screening of the sublibraries revealed selective 5-HT<sub>2A</sub> inverse agonists with IC-50 values between 10 and 100 nM.</p>}},
  author       = {{Husemoen, Gitte and Olsson, Roger and Andersson, Carl Magnus and Harvey, Scott C. and Hansen, Henrik C.}},
  issn         = {{1520-4766}},
  language     = {{eng}},
  number       = {{5}},
  pages        = {{606--609}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Journal of Combinatorial Chemistry}},
  title        = {{Solution-phase parallel Wittig olefination : Synthesis of substituted 1,2-diarylethanes}},
  url          = {{http://dx.doi.org/10.1021/cc0300210}},
  doi          = {{10.1021/cc0300210}},
  volume       = {{5}},
  year         = {{2003}},
}