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Optimization of 4,6-bis-anilino-1H-pyrrolo[2,3-d]pyrimidine IGF-1R tyrosine kinase inhibitors towards JNK selectivity.

Chamberlain SD, Redman AM, Wilson JW, Deanda F, Shotwell JB, Gerding R, Lei H, Yang B, Stevens KL, Hassell AM, Shewchuk LM, Leesnitzer MA, Smith JL, Sabbatini P, Atkins C, Groy A, Rowand JL, Kumar R, Mook RA, Moorthy G, Patnaik S
Bioorg Med Chem Lett 19 360-4 (2009)
Cited: 30 times
EuropePMC logo PMID: 19071018

Abstract

The SAR of C5' functional groups with terminal basic amines at the C6 aniline of 4,6-bis-anilino-1H-pyrrolo[2,3-d]pyrimidines is reported. Examples demonstrate potent inhibition of IGF-1R with 1000-fold selectivity over JNK1 and 3 in enzymatic assays.

Reviews - 3ekn mentioned but not cited (1)

  1. Evaluation of the Anti-Diabetic Activity of Some Common Herbs and Spices: Providing New Insights with Inverse Virtual Screening. Pereira ASP, Banegas-Luna AJ, Peña-García J, Pérez-Sánchez H, Apostolides Z. Molecules 24 E4030 (2019)

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  1. Predicting new indications for approved drugs using a proteochemometric method. Dakshanamurthy S, Issa NT, Assefnia S, Seshasayee A, Peters OJ, Madhavan S, Uren A, Brown ML, Byers SW. J Med Chem 55 6832-6848 (2012)
  2. Exploring African Medicinal Plants for Potential Anti-Diabetic Compounds with the DIA-DB Inverse Virtual Screening Web Server. Pereira ASP, den Haan H, Peña-García J, Moreno MM, Pérez-Sánchez H, Apostolides Z. Molecules 24 E2002 (2019)
  3. Conformational transition paths harbor structures useful for aiding drug discovery and understanding enzymatic mechanisms in protein kinases. Wong CF. Protein Sci 25 192-203 (2016)
  4. A Drug-Target Network-Based Approach to Evaluate the Efficacy of Medicinal Plants for Type II Diabetes Mellitus. Gu J, Chen L, Yuan G, Xu X. Evid Based Complement Alternat Med 2013 203614 (2013)
  5. Computation Screening of Multi-Target Antidiabetic Properties of Phytochemicals in Common Edible Mediterranean Plants. Goulas V, Banegas-Luna AJ, Constantinou A, Pérez-Sánchez H, Barbouti A. Plants (Basel) 11 1637 (2022)
  6. Computational Study of Asian Propolis Compounds as Potential Anti-Type 2 Diabetes Mellitus Agents by Using Inverse Virtual Screening with the DIA-DB Web Server, Tanimoto Similarity Analysis, and Molecular Dynamic Simulation. Syaifie PH, Harisna AH, Nasution MAF, Arda AG, Nugroho DW, Jauhar MM, Mardliyati E, Maulana NN, Rochman NT, Noviyanto A, Banegas-Luna AJ, Pérez-Sánchez H. Molecules 27 3972 (2022)
  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. Fishing the Targets of Bioactive Compounds from Psidium guajava L. Leaves in the Context of Diabetes. Díaz-de-Cerio E, Girón F, Pérez-Garrido A, Pereira ASP, Gabaldón-Hernández JA, Verardo V, Segura Carretero A, Pérez-Sánchez H. Int J Mol Sci 24 5761 (2023)


Reviews citing this publication (6)

  1. Inhibition of the insulin-like growth factor-1 receptor (IGF1R) tyrosine kinase as a novel cancer therapy approach. Li R, Pourpak A, Morris SW. J Med Chem 52 4981-5004 (2009)
  2. JNK1, a potential therapeutic target for hepatocellular carcinoma. Chen F, Beezhold K, Castranova V. Biochim Biophys Acta 1796 242-251 (2009)
  3. ALK and ROS1 as a joint target for the treatment of lung cancer: a review. Puig de la Bellacasa R, Karachaliou N, Estrada-Tejedor R, Teixidó J, Costa C, Borrell JI. Transl Lung Cancer Res 2 72-86 (2013)
  4. Inhibitors of anaplastic lymphoma kinase: a patent review. Milkiewicz KL, Ott GR. Expert Opin Ther Pat 20 1653-1681 (2010)
  5. A Perspective on the Development of c-Jun N-terminal Kinase Inhibitors as Therapeutics for Alzheimer's Disease: Investigating Structure through Docking Studies. Cho H, Hah JM. Biomedicines 9 1431 (2021)
  6. Recent developments in the structural characterisation of the IR and IGF1R: implications for the design of IR-IGF1R hybrid receptor modulators. Turvey SJ, McPhillie MJ, Kearney MT, Muench SP, Simmons KJ, Fishwick CWG. RSC Med Chem 13 360-374 (2022)

Articles citing this publication (15)

  1. Identification and structure-function analysis of subfamily selective G protein-coupled receptor kinase inhibitors. Homan KT, Larimore KM, Elkins JM, Szklarz M, Knapp S, Tesmer JJ. ACS Chem Biol 10 310-319 (2015)
  2. Analysis of conditions affecting auto-phosphorylation of human kinases during expression in bacteria. Shrestha A, Hamilton G, O'Neill E, Knapp S, Elkins JM. Protein Expr Purif 81 136-143 (2012)
  3. Understanding the specificity of a docking interaction between JNK1 and the scaffolding protein JIP1. Yan C, Kaoud T, Lee S, Dalby KN, Ren P. J Phys Chem B 115 1491-1502 (2011)
  4. Enzyme kinetics and interaction studies for human JNK1β1 and substrates activating transcription factor 2 (ATF2) and c-Jun N-terminal kinase (c-Jun). Figuera-Losada M, LoGrasso PV. J Biol Chem 287 13291-13302 (2012)
  5. IGF1R regulates retrograde axonal transport of signalling endosomes in motor neurons. Fellows AD, Rhymes ER, Gibbs KL, Greensmith L, Schiavo G. EMBO Rep 21 e49129 (2020)
  6. Potent Pyrimidine and Pyrrolopyrimidine Inhibitors of Testis-Specific Serine/Threonine Kinase 2 (TSSK2). Hawkinson JE, Sinville R, Mudaliar D, Shetty J, Ward T, Herr JC, Georg GI. ChemMedChem 12 1857-1865 (2017)
  7. 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)
  8. Synthesis and fungicidal activity of pyrazole derivatives containing 1,2,3,4-tetrahydroquinoline. Lei P, Zhang X, Xu Y, Xu G, Liu X, Yang X, Zhang X, Ling Y. Chem Cent J 10 40 (2016)
  9. Radiosynthesis and evaluation of IGF1R PET ligand [11C]GSK1838705A. Solingapuram Sai KK, Prabhakaran J, Sattiraju A, Mann JJ, Mintz A, Kumar JSD. Bioorg Med Chem Lett 27 2895-2897 (2017)
  10. Cyclopentyl-pyrimidine based analogues as novel and potent IGF-1R inhibitor. Aware V, Gaikwad N, Chavan S, Manohar S, Bose J, Khanna S, B-Rao C, Dixit N, Singh KS, Damre A, Sharma R, Patil S, Roychowdhury A. Eur J Med Chem 92 246-256 (2015)
  11. Effect of Cd, Zn and Hg complexes of barbituric acid and thiouracil on rat brain monoamine oxidase-B (in vitro). Shaban NZ, Masoud MS, Awad D, Mawlawi MA, Sadek OM. Chem Biol Interact 208 37-46 (2014)
  12. JNK1β1 is phosphorylated during expression in E. coli and in vitro by MKK4 at three identical novel sites. Owen GR, Stoychev S, Achilonu I, Dirr HW. Biochem Biophys Res Commun 432 683-688 (2013)
  13. Profiling MAP kinase cysteines for targeted covalent inhibitor design. Liu R, Verma N, Henderson JA, Zhan S, Shen J. RSC Med Chem 13 54-63 (2022)
  14. Structural requirements of isoquinolones as novel selective c-Jun N-terminal kinase 1 inhibitors: 2D and 3D QSAR analyses. Du J, Xi L, Lei B, Liu H, Yao X. Chem Biol Drug Des 77 248-254 (2011)
  15. Spectral studies on a series of metal ion complexes derived from pyrimidine nucleus, TEM, biological and γ-irradiation effect. Al-Ashqer S, Abou-Melha KS, Al-Hazmi GA, Saad FA, El-Metwaly NM. Spectrochim Acta A Mol Biomol Spectrosc 132 751-761 (2014)


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