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Acyclic cyanamide-based inhibitors of cathepsin K.

Barrett DG, Deaton DN, Hassell AM, McFadyen RB, Miller AB, Miller LR, Payne JA, Shewchuk LM, Willard DH, Wright LL
Bioorg Med Chem Lett 15 3039-43 (2005)
Cited: 12 times
EuropePMC logo PMID: 15896958

Abstract

Conversion of the proline-derived cyanamide lead to an acyclic cyanamide capable of forming an additional hydrogen bond with cathepsin K resulted in a large increase in inhibitory activity. An X-ray structure of a co-crystal of a cyanamide with cathepsin K confirmed the enzyme interaction. Furthermore, a representative acyclic cyanamide inhibitor 6r was able to attenuate bone resorption in the rat calvarial model.

Reviews citing this publication (2)

  1. Biochemical properties and regulation of cathepsin K activity. Lecaille F, Brömme D, Lalmanach G. Biochimie 90 208-226 (2008)
  2. Cryo-EM: A new dawn in thyroid biology. Coscia F, Taler-Verčič A. Mol Cell Endocrinol 531 111309 (2021)

Articles citing this publication (10)

  1. A generally applicable method for assessing the electrophilicity and reactivity of diverse nitrile-containing compounds. Oballa RM, Truchon JF, Bayly CI, Chauret N, Day S, Crane S, Berthelette C. Bioorg Med Chem Lett 17 998-1002 (2007)
  2. New Frontiers in Druggability. Kozakov D, Hall DR, Napoleon RL, Yueh C, Whitty A, Vajda S. J Med Chem 58 9063-9088 (2015)
  3. Selective activity-based probes for cysteine cathepsins. Watzke A, Kosec G, Kindermann M, Jeske V, Nestler HP, Turk V, Turk B, Wendt KU. Angew Chem Int Ed Engl 47 406-409 (2008)
  4. Azadipeptide nitriles: highly potent and proteolytically stable inhibitors of papain-like cysteine proteases. Löser R, Frizler M, Schilling K, Gütschow M. Angew Chem Int Ed Engl 47 4331-4334 (2008)
  5. 3D QSAR studies on ketoamides of human cathepsin K inhibitors based on two different alignment methods. Pan X, Tan N, Zeng G, Huang H, Yan H. Eur J Med Chem 45 667-681 (2010)
  6. Enzymatic enantiomeric resolution of phenylethylamines structurally related to amphetamine. Muñoz L, Rodriguez AM, Rosell G, Bosch MP, Guerrero A. Org Biomol Chem 9 8171-8177 (2011)
  7. Double duty for cyanogen bromide in a cascade synthesis of cyanoepoxides. Li Z, Gevorgyan V. Angew Chem Int Ed Engl 50 2808-2810 (2011)
  8. 3-Cyano-3-aza-β-amino Acid Derivatives as Inhibitors of Human Cysteine Cathepsins. Schmitz J, Beckmann AM, Dudic A, Li T, Sellier R, Bartz U, Gütschow M. ACS Med Chem Lett 5 1076-1081 (2014)
  9. Conformational Properties of New Thiosemicarbazone and Thiocarbohydrazone Derivatives and Their Possible Targets. Georgiou N, Katsogiannou A, Skourtis D, Iatrou H, Tzeli D, Vassiliou S, Javornik U, Plavec J, Mavromoustakos T. Molecules 27 2537 (2022)
  10. Hydrodehalogenation of alkyl iodides with base-mediated hydrogenation and catalytic transfer hydrogenation: application to the asymmetric synthesis of N-protected α-methylamines. Mandal PK, Birtwistle JS, McMurray JS. J Org Chem 79 8422-8427 (2014)


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