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Improved synthesis of chiral pyrrolidine inhibitors and their binding properties to neuronal nitric oxide synthase.

Xue F, Kraus JM, Labby KJ, Ji H, Mataka J, Xia G, Li H, Delker SL, Roman LJ, Martásek P, Poulos TL, Silverman RB
J Med Chem 54 6399-403 (2011)
Related entries: 3pnf, 3png, 3pnh, 3svp, 3svq

Cited: 6 times
EuropePMC logo PMID: 21809851

Abstract

We report an efficient synthetic route to chiral pyrrolidine inhibitors of neuronal nitric oxide synthase (nNOS) and crystal structures of the inhibitors bound to nNOS and to endothelial NOS. The new route enables versatile structure-activity relationship studies on the pyrrolidine-based scaffold, which can be beneficial for further development of nNOS inhibitors. The X-ray crystal structures of five new fluorine-containing inhibitors bound to nNOS provide insights into the effect of the fluorine atoms on binding.

Articles - 3pne mentioned but not cited (1)

  1. Improved synthesis of chiral pyrrolidine inhibitors and their binding properties to neuronal nitric oxide synthase. Xue F, Kraus JM, Labby KJ, Ji H, Mataka J, Xia G, Li H, Delker SL, Roman LJ, Martásek P, Poulos TL, Silverman RB. J Med Chem 54 6399-6403 (2011)


Reviews citing this publication (1)

  1. Development of nitric oxide synthase inhibitors for neurodegeneration and neuropathic pain. Mukherjee P, Cinelli MA, Kang S, Silverman RB. Chem Soc Rev 43 6814-6838 (2014)

Articles citing this publication (4)

  1. Intramolecular hydrogen bonding: a potential strategy for more bioavailable inhibitors of neuronal nitric oxide synthase. Labby KJ, Xue F, Kraus JM, Ji H, Mataka J, Li H, Martásek P, Roman LJ, Poulos TL, Silverman RB. Bioorg Med Chem 20 2435-2443 (2012)
  2. Cyclopropyl- and methyl-containing inhibitors of neuronal nitric oxide synthase. Li H, Xue F, Kraus JM, Ji H, Labby KJ, Mataka J, Delker SL, Martásek P, Roman LJ, Poulos TL, Silverman RB. Bioorg Med Chem 21 1333-1343 (2013)
  3. High yielding allylation of a chiral secondary alcohol containing base sensitive functional groups. Kraus JM, Gits HC, Silverman RB. Tetrahedron Lett 53 1319-1322 (2012)
  4. Immobilization of growing Sphingomonas sp. HXN-200 to gelatin microspheres: efficient biotransformation of N-Cbz-pyrrolidine and N-Boc-pyrrolidine into hydroxypyrrolidine derivatives. Wang L, Loh KC, Tong YW. J Biotechnol 182-183 74-82 (2014)


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