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Benzothiophene inhibitors of MK2. Part 2: improvements in kinase selectivity and cell potency.

Anderson DR, Meyers MJ, Kurumbail RG, Caspers N, Poda GI, Long SA, Pierce BS, Mahoney MW, Mourey RJ, Parikh MD
Bioorg Med Chem Lett 19 4882-4 (2009)
Related entries: 3fyj, 3fz1

Cited: 23 times
EuropePMC logo PMID: 19616942

Abstract

Optimization of kinase selectivity for a set of benzothiophene MK2 inhibitors provided analogs with potencies of less than 500 nM in a cell based assay. The selectivity of the inhibitors can be rationalized by examination of X-ray crystal structures of inhibitors bound to MK2.

Reviews - 3fyk mentioned but not cited (2)

  1. Targeting Mitogen-Activated Protein Kinase-Activated Protein Kinase 2 (MAPKAPK2, MK2): Medicinal Chemistry Efforts To Lead Small Molecule Inhibitors to Clinical Trials. Fiore M, Forli S, Manetti F. J Med Chem 59 3609-3634 (2016)
  2. Privileged diazepine compounds and their emergence as bromodomain inhibitors. Smith SG, Sanchez R, Zhou MM. Chem Biol 21 573-583 (2014)

Articles - 3fyk mentioned but not cited (4)

  1. Protein-protein docking benchmark version 4.0. Hwang H, Vreven T, Janin J, Weng Z. Proteins 78 3111-3114 (2010)
  2. Binding affinity prediction for ligands and receptors forming tautomers and ionization species: inhibition of mitogen-activated protein kinase-activated protein kinase 2 (MK2). Natesan S, Subramaniam R, Bergeron C, Balaz S. J Med Chem 55 2035-2047 (2012)
  3. Changes in protein structure at the interface accompanying complex formation. Chakravarty D, Janin J, Robert CH, Chakrabarti P. IUCrJ 2 643-652 (2015)
  4. 1,4-Thienodiazepine-2,5-diones via MCR (II): scaffold hopping by Gewald and Ugi-deprotection-cyclization strategy. Huang Y, Dömling A. Chem Biol Drug Des 76 130-141 (2010)


Articles citing this publication (17)

  1. A benzothiophene inhibitor of mitogen-activated protein kinase-activated protein kinase 2 inhibits tumor necrosis factor alpha production and has oral anti-inflammatory efficacy in acute and chronic models of inflammation. Mourey RJ, Burnette BL, Brustkern SJ, Daniels JS, Hirsch JL, Hood WF, Meyers MJ, Mnich SJ, Pierce BS, Saabye MJ, Schindler JF, South SA, Webb EG, Zhang J, Anderson DR. J Pharmacol Exp Ther 333 797-807 (2010)
  2. MAPK-activated protein kinase 2 contributes to Clostridium difficile-associated inflammation. Bobo LD, El Feghaly RE, Chen YS, Dubberke ER, Han Z, Baker AH, Li J, Burnham CA, Haslam DB. Infect Immun 81 713-722 (2013)
  3. Novel 3-aminopyrazole inhibitors of MK-2 discovered by scaffold hopping strategy. Velcicky J, Feifel R, Hawtin S, Heng R, Huppertz C, Koch G, Kroemer M, Moebitz H, Revesz L, Scheufler C, Schlapbach A. Bioorg Med Chem Lett 20 1293-1297 (2010)
  4. Inhibition of the protein kinase MK-2 protects podocytes from nephrotic syndrome-related injury. Pengal R, Guess AJ, Agrawal S, Manley J, Ransom RF, Mourey RJ, Benndorf R, Smoyer WE. Am J Physiol Renal Physiol 301 F509-19 (2011)
  5. A three-step protocol for lead optimization: quick identification of key conformational features and functional groups in the SAR studies of non-ATP competitive MK2 (MAPKAPK2) inhibitors. Huang X, Zhu X, Chen X, Zhou W, Xiao D, Degrado S, Aslanian R, Fossetta J, Lundell D, Tian F, Trivedi P, Palani A. Bioorg Med Chem Lett 22 65-70 (2012)
  6. In vivo and in vitro SAR of tetracyclic MAPKAP-K2 (MK2) inhibitors. Part II. Revesz L, Schlapbach A, Aichholz R, Dawson J, Feifel R, Hawtin S, Littlewood-Evans A, Koch G, Kroemer M, Möbitz H, Scheufler C, Velcicky J, Huppertz C. Bioorg Med Chem Lett 20 4719-4723 (2010)
  7. Novel ATP competitive MK2 inhibitors with potent biochemical and cell-based activity throughout the series. Oubrie A, Kaptein A, de Zwart E, Hoogenboom N, Goorden R, van de Kar B, van Hoek M, de Kimpe V, van der Heijden R, Borsboom J, Kazemier B, de Roos J, Scheffers M, Lommerse J, Schultz-Fademrecht C, Barf T. Bioorg Med Chem Lett 22 613-618 (2012)
  8. Adaptive Cartesian and torsional restraints for interactive model rebuilding. Croll TI, Read RJ. Acta Crystallogr D Struct Biol 77 438-446 (2021)
  9. Facile synthesis of tetracyclic azepine and oxazocine derivatives and their potential as MAPKAP-K2 (MK2) inhibitors. Rao AU, Xiao D, Huang X, Zhou W, Fossetta J, Lundell D, Tian F, Trivedi P, Aslanian R, Palani A. Bioorg Med Chem Lett 22 1068-1072 (2012)
  10. In vivo and in vitro SAR of tetracyclic MAPKAP-K2 (MK2) inhibitors. Part I. Revesz L, Schlapbach A, Aichholz R, Feifel R, Hawtin S, Heng R, Hiestand P, Jahnke W, Koch G, Kroemer M, Möbitz H, Scheufler C, Velcicky J, Huppertz C. Bioorg Med Chem Lett 20 4715-4718 (2010)
  11. Microwave-assisted synthesis of 3-aminobenzo[b]thiophene scaffolds for the preparation of kinase inhibitors. Bagley MC, Dwyer JE, Molina MD, Rand AW, Rand HL, Tomkinson NC. Org Biomol Chem 13 6814-6824 (2015)
  12. A computational study on thiourea analogs as potent MK-2 inhibitors. Hao M, Ren H, Luo F, Zhang S, Qiu J, Ji M, Si H, Li G. Int J Mol Sci 13 7057-7079 (2012)
  13. Antimalarials with Benzothiophene Moieties as Aminoquinoline Partners. Konstantinović J, Videnović M, Srbljanović J, Djurković-Djaković O, Bogojević K, Sciotti R, Šolaja B. Molecules 22 E343 (2017)
  14. Discovery of a Potent Dihydrooxadiazole Series of Non-ATP-Competitive MK2 (MAPKAPK2) Inhibitors. Qin J, Dhondi P, Huang X, Aslanian R, Fossetta J, Tian F, Lundell D, Palani A. ACS Med Chem Lett 3 100-105 (2012)
  15. Microwave-Assisted Synthesis of a MK2 Inhibitor by Suzuki-Miyaura Coupling for Study in Werner Syndrome Cells. Bagley MC, Baashen M, Chuckowree I, Dwyer JE, Kipling D, Davis T. Pharmaceuticals (Basel) 8 257-276 (2015)
  16. Pharmacological and genetic inhibition of downstream targets of p38 MAPK in experimental nephrotic syndrome. Nie X, Chanley MA, Pengal R, Thomas DB, Agrawal S, Smoyer WE. Am J Physiol Renal Physiol 314 F602-F613 (2018)
  17. Structural analysis of an MK2-inhibitor complex: insight into the regulation of the secondary structure of the Gly-rich loop by TEI-I01800. Fujino A, Fukushima K, Namiki N, Kosugi T, Takimoto-Kamimura M. Acta Crystallogr D Biol Crystallogr 66 80-87 (2010)


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