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Discovery of novel 2,3-diarylfuro[2,3-b]pyridin-4-amines as potent and selective inhibitors of Lck: synthesis, SAR, and pharmacokinetic properties.

Martin MW, Newcomb J, Nunes JJ, Bemis JE, McGowan DC, White RD, Buchanan JL, DiMauro EF, Boucher C, Faust T, Hsieh F, Huang X, Lee JH, Schneider S, Turci SM, Zhu X
Bioorg Med Chem Lett 17 2299-304 (2007)
Cited: 13 times
EuropePMC logo PMID: 17276681

Abstract

2,3-Diarylfuro[2,3-b]pyridine-4-amines are a novel class of potent and selective inhibitors of Lck. The discovery, synthesis, and structure activity relationships of this series of inhibitors are reported. The most promising compounds were also profiled to deduce their pharmacokinetic properties.

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  1. 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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  1. Mechanisms of drug resistance in kinases. Barouch-Bentov R, Sauer K. Expert Opin Investig Drugs 20 153-208 (2011)
  2. Update on lymphocyte specific kinase inhibitors: a patent survey. Martin MW, Machacek MR. Expert Opin Ther Pat 20 1573-1593 (2010)
  3. DOCKSTRING: Easy Molecular Docking Yields Better Benchmarks for Ligand Design. García-Ortegón M, Simm GNC, Tripp AJ, Hernández-Lobato JM, Bender A, Bacallado S. J Chem Inf Model 62 3486-3502 (2022)
  4. New horizons in drug discovery of lymphocyte-specific protein tyrosine kinase (Lck) inhibitors: a decade review (2011-2021) focussing on structure-activity relationship (SAR) and docking insights. Elkamhawy A, Ali EMH, Lee K. J Enzyme Inhib Med Chem 36 1574-1602 (2021)

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  1. Improving Protein-Ligand Docking Results with High-Throughput Molecular Dynamics Simulations. Guterres H, Im W. J Chem Inf Model 60 2189-2198 (2020)
  2. Kinase inhibitors for the treatment of inflammatory and autoimmune disorders. Bhagwat SS. Purinergic Signal 5 107-115 (2009)
  3. Development of novel ACK1/TNK2 inhibitors using a fragment-based approach. Lawrence HR, Mahajan K, Luo Y, Zhang D, Tindall N, Huseyin M, Gevariya H, Kazi S, Ozcan S, Mahajan NP, Lawrence NJ. J Med Chem 58 2746-2763 (2015)
  4. Subtle Dynamic Changes Accompany Hck Activation by HIV-1 Nef and are Reversed by an Antiretroviral Kinase Inhibitor. Wales TE, Hochrein JM, Morgan CR, Emert-Sedlak LA, Smithgall TE, Engen JR. Biochemistry 54 6382-6391 (2015)
  5. The discovery of (R)-2-(sec-butylamino)-N-(2-methyl-5-(methylcarbamoyl)phenyl) thiazole-5-carboxamide (BMS-640994)-A potent and efficacious p38alpha MAP kinase inhibitor. Hynes J, Wu H, Pitt S, Shen DR, Zhang R, Schieven GL, Gillooly KM, Shuster DJ, Taylor TL, Yang X, McIntyre KW, McKinnon M, Zhang H, Marathe PH, Doweyko AM, Kish K, Kiefer SE, Sack JS, Newitt JA, Barrish JC, Dodd J, Leftheris K. Bioorg Med Chem Lett 18 1762-1767 (2008)
  6. Discovery of New Pyrazolopyridine, Furopyridine, and Pyridine Derivatives as CDK2 Inhibitors: Design, Synthesis, Docking Studies, and Anti-Proliferative Activity. Abdel-Rahman AA, Shaban AKF, Nassar IF, El-Kady DS, Ismail NSM, Mahmoud SF, Awad HM, El-Sayed WA. Molecules 26 3923 (2021)
  7. QM/QM docking method based on the variational finite localized molecular orbital approximation. Anisimov VM, Bugaenko VL. J Comput Chem 30 784-798 (2009)
  8. Concise, gram-scale synthesis of furo[2,3-b]pyridines with functional handles for chemoselective cross-coupling. O'Byrne SN, Eduful BJ, Willson TM, Drewry DH. Tetrahedron Lett 61 152353 (2020)


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