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2-aminopyridines as highly selective inducible nitric oxide synthase inhibitors. Differential binding modes dependent on nitrogen substitution

Academic Article
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Overview

authors

  • Connolly, S.
  • Aberg, A.
  • Arvai, A.
  • Beaton, H. G.
  • Cheshire, D. R.
  • Cook, A. R.
  • Cooper, S.
  • Cox, D.
  • Hamley, P.
  • Mallinder, P.
  • Millichip, I.
  • Nicholls, D. J.
  • Gunn, Robin Rosenfeld
  • St-Gallay, S. A.
  • Tainer, John
  • Tinker, A. C.
  • Wallace, A. V.

publication date

  • June 2004

journal

  • Journal of Medicinal Chemistry  Journal

abstract

  • 4-Methylaminopyridine (4-MAP) (5) is a potent but nonselective nitric oxide synthase (NOS) inhibitor. While simple N-methylation in this series results in poor activity, more elaborate N-substitution such as with 4-piperidine carbamate or amide results in potent and selective inducible NOS inhibition. Evidently, a flipping of the pyridine ring between these new inhibitors allows the piperidine to interact with different residues and confer excellent selectivity.

subject areas

  • Aminopyridines
  • Animals
  • Crystallography, X-Ray
  • Mice
  • Models, Molecular
  • Nitric Oxide Synthase
  • Nitric Oxide Synthase Type II
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Identity

International Standard Serial Number (ISSN)

  • 0022-2623

Digital Object Identifier (DOI)

  • 10.1021/jm031035n

PubMed ID

  • 15163211
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Additional Document Info

start page

  • 3320

end page

  • 3323

volume

  • 47

issue

  • 12

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