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Novel potent and efficacious nonpeptidic urotensin II receptor agonists

Lehmann, Fredrik ; Pettersen, Anna ; Currier, Erika A. ; Sherbukhin, Vladimir ; Olsson, Roger LU orcid ; Hacksell, Uli and Luthman, Kristina (2006) In Journal of Medicinal Chemistry 49(7). p.2232-2240
Abstract

Six different series of nonpeptidic urotensin II receptor agonists have been synthesized and evaluated for their agonistic activity in a cell-based assay (R-SAT). The compounds are ring-opened analogues of the isochromanone-based agonist AC-7954 with different functionalities constituting the linker between the two aromatic ring moieties. Several of the compounds are highly potent and efficacious, with N-[1-(4-chlorophenyl)-3-(dimethylamino)- propyl]-4-phenylbenzamide oxalate (5d) being the most potent. The pure enantiomers of 5d were obtained from the corresponding diastereomeric amides. It was shown by a combination of X-ray crystallography and chemical correlation that the activity resides in the S-enantiomer of 5d (pEC50... (More)

Six different series of nonpeptidic urotensin II receptor agonists have been synthesized and evaluated for their agonistic activity in a cell-based assay (R-SAT). The compounds are ring-opened analogues of the isochromanone-based agonist AC-7954 with different functionalities constituting the linker between the two aromatic ring moieties. Several of the compounds are highly potent and efficacious, with N-[1-(4-chlorophenyl)-3-(dimethylamino)- propyl]-4-phenylbenzamide oxalate (5d) being the most potent. The pure enantiomers of 5d were obtained from the corresponding diastereomeric amides. It was shown by a combination of X-ray crystallography and chemical correlation that the activity resides in the S-enantiomer of 5d (pEC50 7.49).

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author
; ; ; ; ; and
publishing date
type
Contribution to journal
publication status
published
in
Journal of Medicinal Chemistry
volume
49
issue
7
pages
9 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • pmid:16570919
  • scopus:33645669146
ISSN
0022-2623
DOI
10.1021/jm051121i
language
English
LU publication?
no
id
adf28454-70e4-4762-9dfe-9706dc64357a
date added to LUP
2019-10-02 10:30:50
date last changed
2025-10-14 10:35:33
@article{adf28454-70e4-4762-9dfe-9706dc64357a,
  abstract     = {{<p>Six different series of nonpeptidic urotensin II receptor agonists have been synthesized and evaluated for their agonistic activity in a cell-based assay (R-SAT). The compounds are ring-opened analogues of the isochromanone-based agonist AC-7954 with different functionalities constituting the linker between the two aromatic ring moieties. Several of the compounds are highly potent and efficacious, with N-[1-(4-chlorophenyl)-3-(dimethylamino)- propyl]-4-phenylbenzamide oxalate (5d) being the most potent. The pure enantiomers of 5d were obtained from the corresponding diastereomeric amides. It was shown by a combination of X-ray crystallography and chemical correlation that the activity resides in the S-enantiomer of 5d (pEC<sub>50</sub> 7.49).</p>}},
  author       = {{Lehmann, Fredrik and Pettersen, Anna and Currier, Erika A. and Sherbukhin, Vladimir and Olsson, Roger and Hacksell, Uli and Luthman, Kristina}},
  issn         = {{0022-2623}},
  language     = {{eng}},
  month        = {{04}},
  number       = {{7}},
  pages        = {{2232--2240}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Journal of Medicinal Chemistry}},
  title        = {{Novel potent and efficacious nonpeptidic urotensin II receptor agonists}},
  url          = {{http://dx.doi.org/10.1021/jm051121i}},
  doi          = {{10.1021/jm051121i}},
  volume       = {{49}},
  year         = {{2006}},
}