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Discovery, synthesis and biological evaluation of isoquinolones as novel and highly selective JNK inhibitors (2).

Asano Y, Kitamura S, Ohra T, Itoh F, Kajino M, Tamura T, Kaneko M, Ikeda S, Igata H, Kawamoto T, Sogabe S, Matsumoto S, Tanaka T, Yamaguchi M, Kimura H, Fukumoto S
Bioorg Med Chem 16 4699-714 (2008)
Cited: 24 times
EuropePMC logo PMID: 18313930

Abstract

3-Metoxycarbonyl isoquinolone derivative 1 has been identified as a potent JNK inhibitor and significantly inhibited cardiac hypertrophy in a rat pressure-overload model. Herein, a series of isoquinolones with an imidazolylmethyl or a pyrazolylmethyl group at the 2-position were designed based on X-ray crystallographic analysis of the complex between the isoquinolone compound and JNK3, as wells as the relationship between compound lipophilicity (logD) and activity in a cell-based assay. The compounds prepared showed potent JNK1 inhibitory activities in a cell-based assay. Among them the isoquinolone derivative possessing 5-[(cyclopropylamino)carbonyl]-1-methyl-1H-pyrazole (16e) exhibited significant anti-hypertrophic activity at doses of more than 1mg/kg (po) in a pressure-overload model.

Articles - 2zdt mentioned but not cited (4)

  1. Directory of useful decoys, enhanced (DUD-E): better ligands and decoys for better benchmarking. Mysinger MM, Carchia M, Irwin JJ, Shoichet BK. J Med Chem 55 6582-6594 (2012)
  2. Identification of gefitinib off-targets using a structure-based systems biology approach; their validation with reverse docking and retrospective data mining. Verma N, Rai AK, Kaushik V, Brünnert D, Chahar KR, Pandey J, Goyal P. Sci Rep 6 33949 (2016)
  3. Correlation between Virtual Screening Performance and Binding Site Descriptors of Protein Targets. Shamsara J. Int J Med Chem 2018 3829307 (2018)
  4. Effect of Binding Pose and Modeled Structures on SVMGen and GlideScore Enrichment of Chemical Libraries. Xu D, Meroueh SO. J Chem Inf Model 56 1139-1151 (2016)


Reviews citing this publication (2)

  1. C-Jun N-terminal kinase inhibitors: Structural insight into kinase-inhibitor complexes. Duong MTH, Lee JH, Ahn HC. Comput Struct Biotechnol J 18 1440-1457 (2020)
  2. Advances in Immunosuppressive Agents Based on Signal Pathway. Xu Z, Chu M. Front Pharmacol 13 917162 (2022)

Articles citing this publication (18)

  1. Concise copper-catalyzed one-pot tandem synthesis of benzimidazo[1,2-b]isoquinolin-11-one derivatives. Lu J, Gong X, Yang H, Fu H. Chem Commun (Camb) 46 4172-4174 (2010)
  2. Cinchonamine Squaramide Catalyzed Asymmetric aza-Michael Reaction: Dihydroisoquinolines and Tetrahydropyridines. Roy TK, Parhi B, Ghorai P. Angew Chem Int Ed Engl 57 9397-9401 (2018)
  3. A simple access to N-(un)substituted isoquinolin-1(2H)-ones: unusual formation of regioisomeric isoquinolin-1(4H)-ones. Chary RG, Dhananjaya G, Prasad KV, Vaishaly S, Ganesh YS, Dulla B, Kumar KS, Pal M. Chem Commun (Camb) 50 6797-6800 (2014)
  4. Letter Development of indole/indazole-aminopyrimidines as inhibitors of c-Jun N-terminal kinase (JNK): optimization for JNK potency and physicochemical properties. Gong L, Han X, Silva T, Tan YC, Goyal B, Tivitmahaisoon P, Trejo A, Palmer W, Hogg H, Jahagir A, Alam M, Wagner P, Stein K, Filonova L, Loe B, Makra F, Rotstein D, Rapatova L, Dunn J, Zuo F, Dal Porto J, Wong B, Jin S, Chang A, Tran P, Hsieh G, Niu L, Shao A, Reuter D, Hermann J, Kuglstatter A, Goldstein D. Bioorg Med Chem Lett 23 3565-3569 (2013)
  5. Discovery of a novel series of 4-quinolone JNK inhibitors. Gong L, Tan YC, Boice G, Abbot S, McCaleb K, Iyer P, Zuo F, Dal Porto J, Wong B, Jin S, Chang A, Tran P, Hsieh G, Niu L, Shao A, Reuter D, Lukacs CM, Ursula Kammlott R, Kuglstatter A, Goldstein D. Bioorg Med Chem Lett 22 7381-7387 (2012)
  6. An expedient approach to 1,2-dihydroisoquinoline derivatives via cobalt catalysed 6-endo dig cyclization followed by Mannich condensation of o-alkynylarylaldimines. Urvashi, Rastogi GK, Ginotra SK, Agarwal A, Tandon V. Org Biomol Chem 13 1000-1007 (2015)
  7. Efficient copper-catalyzed synthesis of poly-N-heterocycles containing amino acid residues. Liu T, Wang R, Yang H, Fu H. Chemistry 17 6765-6771 (2011)
  8. Palladium-catalyzed carbonylative reactions of 1-bromo-2-fluorobenzenes with various nucleophiles: effective combination of carbonylation and nucleophilic substitution. Chen J, Natte K, Neumann H, Wu XF. Chemistry 20 16107-16110 (2014)
  9. Synthesis of functionalized isoquinolin-1(2H)-ones by copper-catalyzed α-arylation of ketones with 2-halobenzamides. Shi Y, Zhu X, Mao H, Hu H, Zhu C, Cheng Y. Chemistry 19 11553-11557 (2013)
  10. A facile palladium catalysed 3-component cascade route to functionalised isoquinolinones and isoquinolines. Grigg R, Elboray EE, Akkarasamiyo S, Chuanopparat N, Dondas HA, Abbas-Temirek HH, Fishwick CW, Aly MF, Kongkathip B, Kongkathip N. Chem Commun (Camb) 52 164-166 (2016)
  11. A new access to 3-substituted-1(2H)-isoquinolone by tandem palladium-catalyzed intramolecular aminocarbonylation annulation. Dieudonné-Vatran A, Azoulay M, Florent JC. Org Biomol Chem 10 2683-2691 (2012)
  12. A novel 3-acyl isoquinolin-1(2H)-one induces G2 phase arrest, apoptosis and GSDME-dependent pyroptosis in breast cancer. Ma L, Bian M, Gao H, Zhou Z, Yi W. PLoS One 17 e0268060 (2022)
  13. Isoquinolone-4-Carboxylic Acids by Ammonia-Ugi-4CR and Copper-Catalyzed Domino Reaction. Wang Q, Mgimpatsang KC, Li X, Dömling A. J Org Chem 86 9771-9780 (2021)
  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. An integration of condensation/Ullmann-type coupling/bicyclization sequences: copper-catalyzed three-component direct synthesis of [1,2,4]triazolo[1,5-b]isoquinolin-5(1H)-ones. Jia FC, Xu C, Cai Q, Wu AX. Chem Commun (Camb) 50 9914-9916 (2014)
  16. Cobalt-Catalyzed C-H Activation/Annulation of Benzamides with Fluorine-Containing Alkynes: A Route to 3- and 4-Fluoroalkylated Isoquinolinones. Kumon T, Wu J, Shimada M, Yamada S, Agou T, Fukumoto H, Kubota T, Hammond GB, Konno T. J Org Chem 86 5183-5196 (2021)
  17. Novel indolo [3,2-c]isoquinoline-5-one-6-yl [1,2,4]triazolo [3,4-b] [1,3,4]thiadiazole analogues: Design, synthesis, anticancer activity, docking with SARS-CoV-2 Omicron protease and MESP/TD-DFT approaches. Verma VA, Saundane AR, Shamrao R, Meti RS, Shinde VM. J Mol Struct 1264 133153 (2022)
  18. Harnessing Vinyl Acetate as an Acetylene Equivalent in Redox-Neutral Cp*Co(III)-Catalyzed C-H Activation/Annulation for the Synthesis of Isoquinolones and Pyridones. Rana T, Ghosh A, Aher YN, Pawar AB. ACS Omega 8 25262-25271 (2023)


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