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Synthesis of α-trinositol related analogues. Structure-activity (analgesic and anti-inflammatory) relationships

Ballereau, S ; Rehnberg, N LU orcid ; Spiess, B ; Gigg, J ; Gigg, R and Schlewer, G (1997) In European Journal of Medicinal Chemistry 32(6). p.535-540
Abstract

α-Trinositol analogues, including methyl ethers, deoxy, oxa and aza derivatives were prepared. The parent compound possesses weak analgesic and anti-inflammatory properties. Removal of the non-phosphorylated hydroxyls generates a compound devoid of analgesic activity but which retains the anti-inflammatory property of the parent compound. The protection of these hydroxyls as methyl ethers lends to compounds which keep their anti-inflammatory activity, whereas the replacement of the cyclohexane carbone backbone by a tetrahydropyrane or a piperidine ring leads to compounds which increase the pain.

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author
; ; ; ; and
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Analgesic activity, Anti-inflammatory activity, Aza-inositol, Inositol phosphate, Oxa-inositol, α-Trinositol
in
European Journal of Medicinal Chemistry
volume
32
issue
6
pages
6 pages
publisher
Elsevier Masson SAS
external identifiers
  • scopus:0031001478
ISSN
0223-5234
DOI
10.1016/S0223-5234(97)84017-2
language
English
LU publication?
no
id
5c103776-ae11-40d2-93ad-eac7fe63597f
date added to LUP
2021-11-11 13:00:38
date last changed
2022-02-02 01:16:14
@article{5c103776-ae11-40d2-93ad-eac7fe63597f,
  abstract     = {{<p>α-Trinositol analogues, including methyl ethers, deoxy, oxa and aza derivatives were prepared. The parent compound possesses weak analgesic and anti-inflammatory properties. Removal of the non-phosphorylated hydroxyls generates a compound devoid of analgesic activity but which retains the anti-inflammatory property of the parent compound. The protection of these hydroxyls as methyl ethers lends to compounds which keep their anti-inflammatory activity, whereas the replacement of the cyclohexane carbone backbone by a tetrahydropyrane or a piperidine ring leads to compounds which increase the pain.</p>}},
  author       = {{Ballereau, S and Rehnberg, N and Spiess, B and Gigg, J and Gigg, R and Schlewer, G}},
  issn         = {{0223-5234}},
  keywords     = {{Analgesic activity; Anti-inflammatory activity; Aza-inositol; Inositol phosphate; Oxa-inositol; α-Trinositol}},
  language     = {{eng}},
  number       = {{6}},
  pages        = {{535--540}},
  publisher    = {{Elsevier Masson SAS}},
  series       = {{European Journal of Medicinal Chemistry}},
  title        = {{Synthesis of α-trinositol related analogues. Structure-activity (analgesic and anti-inflammatory) relationships}},
  url          = {{http://dx.doi.org/10.1016/S0223-5234(97)84017-2}},
  doi          = {{10.1016/S0223-5234(97)84017-2}},
  volume       = {{32}},
  year         = {{1997}},
}