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Proline isosteres in a series of 2,4-disubstituted pyrrolo[1,2-f][1,2,4]triazine inhibitors of IGF-1R kinase and IR kinase.

Sampognaro AJ, Wittman MD, Carboni JM, Chang C, Greer AF, Hurlburt WW, Sack JS, Vyas DM
Bioorg Med Chem Lett 20 5027-30 (2010)
Related entries: 3nw5, 3nw6

Cited: 15 times
EuropePMC logo PMID: 20675137

Abstract

Pyrrolidine, pyrrolidinone, carbocyclic, and acyclic groups were used as isosteric proline replacements in a series of insulin-like growth factor I receptor kinase/insulin receptor kinase inhibitors. Examples that were similar in potency to proline-containing reference compounds were shown to project a key fluoropyridine amide into a common space, while less potent compounds were not able to do so for reasons of stereochemistry or structural rigidity.

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  4. Identifying three-dimensional structures of autophosphorylation complexes in crystals of protein kinases. Xu Q, Malecka KL, Fink L, Jordan EJ, Duffy E, Kolander S, Peterson JR, Dunbrack RL. Sci Signal 8 rs13 (2015)
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Articles citing this publication (9)

  1. Serine phosphorylation of the insulin-like growth factor I (IGF-1) receptor C-terminal tail restrains kinase activity and cell growth. Kelly GM, Buckley DA, Kiely PA, Adams DR, O'Connor R. J. Biol. Chem. 287 28180-28194 (2012)
  2. A highly selective dual insulin receptor (IR)/insulin-like growth factor 1 receptor (IGF-1R) inhibitor derived from an extracellular signal-regulated kinase (ERK) inhibitor. Anastassiadis T, Duong-Ly KC, Deacon SW, Lafontant A, Ma H, Devarajan K, Dunbrack RL, Wu J, Peterson JR. J. Biol. Chem. 288 28068-28077 (2013)
  3. Dynamic, structural and thermodynamic basis of insulin-like growth factor 1 kinase allostery mediated by activation loop phosphorylation. Li Y, Nam K. Chem Sci 8 3453-3464 (2017)
  4. Synthesis of pyrrolo[2,1-f][1,2,4]triazin-4(3H)-ones: Rearrangement of pyrrolo[1,2-d][1,3,4]oxadiazines and regioselective intramolecular cyclization of 1,2-biscarbamoyl-substituted 1H-pyrroles. Son K, Park SJ. Beilstein J Org Chem 12 1780-1787 (2016)
  5. Possible mechanisms of Leukoagglutinin induced apoptosis in human cells in vitro. Kochubei T, Kitam V, Maksymchuk O, Piven O, Lukash L. Cell Biol. Int. 40 1313-1319 (2016)
  6. PyrrolylBODIPYs: Syntheses, Properties, and Application as Environment-Sensitive Fluorescence Probes. Yu C, Miao W, Wang J, Hao E, Jiao L. ACS Omega 2 3551-3561 (2017)
  7. Virtual screening of specific insulin-like growth factor 1 receptor (IGF1R) inhibitors from the National Cancer Institute (NCI) molecular database. Fan C, Huang YX, Bao YL, Sun LG, Wu Y, Yu CL, Zhang Y, Song ZB, Zheng LH, Sun Y, Wang GN, Li YX. Int J Mol Sci 13 17185-17209 (2012)
  8. Synthetic strategies for pyrrolo[2,1-f][1,2,4]triazine: the parent moiety of antiviral drug remdesivir. Rai GS, Maru JJ. Chem Heterocycl Compd (N Y) 1-6 (2021)
  9. TWN-FS method: A novel fragment screening method for drug discovery. Yoon HR, Park GJ, Balupuri A, Kang NS. Comput Struct Biotechnol J 21 4683-4696 (2023)


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