Design and synthesis of dihydroisoquinolones for fragment-based drug discovery (FBDD)

Organic and Biomolecular Chemistry

Volumn 14, Issue 5, 2016, Pages 1599-1610

  Palmer, Nick ^a   Peakman, Torren M ^a   Norton, David ^a   Rees, David C ^a  

^a ASTEX PHARMACEUTICALS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

POSITIVE IONS;

DRUG DISCOVERY; HETEROATOMS; POTENTIAL BINDING;

CHEMISTRY;

ISOQUINOLINE DERIVATIVE;

CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; DRUG DEVELOPMENT; SYNTHESIS;

DRUG DESIGN; DRUG DISCOVERY; ISOQUINOLINES; MOLECULAR STRUCTURE;

EID: 84956997912     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c5ob02461g     Document Type: Article

References (36)

1. D. Erlanson, Introduction to Fragment-Based Drug Discovery, in Fragment-Based Drug Discovery and X-Ray Crystallography, ed., T. G. Davies, and, M. Hyvönen, Springer, Berlin Heidelberg, 2012, vol. 317, pp. 1-32
2. R. E. Hubbard and J. B. Murray, Chapter twenty-Experiences in Fragment-Based Lead Discovery, in Methods in Enzymology, ed., C. K. Lawrence, Academic Press, 2011, vol. 493, pp. 509-531
3. T. V. Magee Progress in discovery of small-molecule modulators of protein-protein interactions via fragment screening Bioorg. Med. Chem. Lett. 2015 25 12 2461 2468
4. C. W. Murray D. C. Rees The rise of fragment-based drug discovery Nat. Chem. 2009 1 3 187 192
5. E. R. Zartler Fragonomics: The -Omics with Real Impact ACS Med. Chem. Lett. 2014 5 9 952 953
6. J. P. Burke Z. Bian S. Shaw B. Zhao C. M. Goodwin J. Belmar C. F. Browning D. Vigil A. Friberg D. V. Camper O. W. Rossanese T. Lee E. T. Olejniczak S. W. Fesik Discovery of Tricyclic Indoles That Potently Inhibit Mcl-1 Using Fragment-Based Methods and Structure-Based Design J. Med. Chem. 2015 58 9 3794 3805
7. M. Baker Fragment-based lead discovery grows up Nat. Rev. Drug Discovery 2013 12 1 5 7
8. G. Bollag J. Tsai J. Zhang C. Zhang P. Ibrahim K. Nolop P. Hirth Vemurafenib: the first drug approved for BRAF-mutant cancer Nat. Rev. Drug Discovery 2012 11 11 873 886
9. C. W. Murray D. C. Rees Opportunity Knocks: Organic Chemistry for Fragment-Based Drug Discovery (FBDD) Angew. Chem., Int. Ed. 2015 10.1002/anie.201506783
10. M. Congreve R. Carr C. Murray H. Jhoti A 'Rule of Three' for fragment-based lead discovery? Drug Discovery Today 2003 8 19 876 877
11. H. Jhoti G. Williams D. C. Rees C. W. Murray The 'rule of three' for fragment-based drug discovery: where are we now? Nat. Rev. Drug Discovery 2013 12 8 644 644
12. N. Baurin F. Aboul-Ela X. Barril B. Davis M. Drysdale B. Dymock H. Finch C. Fromont C. Richardson H. Simmonite R. E. Hubbard Design and Characterization of Libraries of Molecular Fragments for Use in NMR Screening against Protein Targets J. Chem. Inf. Comput. Sci. 2004 44 6 2157 2166
13. N. Blomberg D. Cosgrove P. Kenny K. Kolmodin Design of compound libraries for fragment screening J. Comput. Aided Mol. Des. 2009 23 8 513 525
14. J. Fejzo C. A. Lepre J. W. Peng G. W. Bemis Ajay M. A. Murcko J. M. Moore The SHAPES strategy: an NMR-based approach for lead generation in drug discovery Chem. Biol. 1999 6 10 755 769
15. W. Lau J. Withka D. Hepworth T. Magee Y. Du G. Bakken M. Miller Z. Hendsch V. Thanabal S. Kolodziej L. Xing Q. Hu L. Narasimhan R. Love M. Charlton S. Hughes W. van Hoorn J. Mills Design of a multi-purpose fragment screening library using molecular complexity and orthogonal diversity metrics J. Comput. Aided Mol. Des. 2011 25 7 621 636
16. A. Schuffenhauer S. Ruedisser A. Marzinzik W. Jahnke P. Selzer E. Jacoby Library Design for Fragment Based Screening Curr. Top. Med. Chem. 2005 5 8 751 762
17. A. D. Morley A. Pugliese K. Birchall J. Bower P. Brennan N. Brown T. Chapman M. Drysdale I. H. Gilbert S. Hoelder A. Jordan S. V. Ley A. Merritt D. Miller M. E. Swarbrick P. G. Wyatt Fragment-based hit identification: thinking in 3D Drug Discovery Today 2013 18 23-24 1221 1227
18. http://www.maggichurchouseevents.co.uk/bmcs/Downloads/Fragments%20-%20Mon%201115%20Brennan%20Paul.pdf
19. B. J. Davis D. A. Erlanson Learning from our mistakes: the 'unknown knowns' in fragment screening Bioorg. Med. Chem. Lett. 2013 23 10 2844 2852
20. M. M. Hann A. R. Leach G. Harper Molecular Complexity and Its Impact on the Probability of Finding Leads for Drug Discovery J. Chem. Inf. Comput. Sci. 2001 41 3 856 864
21. A. R. Leach M. M. Hann Molecular complexity and fragment-based drug discovery: ten years on Curr. Opin. Chem. Biol. 2011 15 4 489 496
22. N. Guimond S. I. Gorelsky K. Fagnou Rhodium(III)-Catalyzed Heterocycle Synthesis Using an Internal Oxidant: Improved Reactivity and Mechanistic Studies J. Am. Chem. Soc. 2011 133 16 6449 6457
23. J. R. Huckins E. A. Bercot O. R. Thiel T.-L. Hwang M. M. Bio Rh(III)-Catalyzed C-H Activation and Double Directing Group Strategy for the Regioselective Synthesis of Naphthyridinones J. Am. Chem. Soc. 2013 135 39 14492 14495
24. T. K. Hyster D. M. Dalton T. Rovis Ligand design for Rh(III)-catalyzed C-H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones Chem. Sci. 2015 6 1 254 258
25. S. Rakshit C. Grohmann T. Besset F. Glorius Rh(III)-Catalyzed Directed C-H Olefination Using an Oxidizing Directing Group: Mild, Efficient, and Versatile J. Am. Chem. Soc. 2011 133 8 2350 2353
26. T. K. Hyster L. Knörr T. R. Ward T. Rovis Biotinylated Rh(III) Complexes in Engineered Streptavidin for Accelerated Asymmetric C-H Activation Science 2012 338 6106 500 503
27. B. Ye N. Cramer Chiral cyclopentadienyl ligands as stereocontrolling element in asymmetric C-H functionalization Science 2012 338 6106 504 506
28. N. J. Webb S. P. Marsden S. A. Raw Rhodium(III)-Catalyzed C-H Activation/Annulation with Vinyl Esters as an Acetylene Equivalent Org. Lett. 2014 16 18 4718 4721
29. B. Ye N. Cramer Asymmetric Synthesis of Isoindolones by Chiral Cyclopentadienyl-Rhodium(III)-Catalyzed C-H Functionalizations Angew. Chem., Int. Ed. 2014 53 30 7896 7899
30. D. Dou P. Viwanathan Y. Li G. He K. R. Alliston G. H. Lushington J. D. Brown-Clay R. Padmanabhan W. C. Groutas Design, Synthesis, and In Vitro Evaluation of Potential West Nile Virus Protease Inhibitors Based on the 1-Oxo-1,2,3,4-tetrahydroisoquinoline and 1-Oxo-1,2-dihydroisoquinoline Scaffolds J. Comb. Chem. 2010 12 6 836 843
31. S. Wu R. Zeng C. Fu Y. Yu X. Zhang S. Ma Rhodium-catalyzed C-H functionalization-based approach to eight-membered lactams Chem. Sci. 2015 6 4 2275 2285
32. N. Guimond C. Gouliaras K. Fagnou Rhodium(III)-Catalyzed Isoquinolone Synthesis: The N-O Bond as a Handle for C-N Bond Formation and Catalyst Turnover J. Am. Chem. Soc. 2010 132 20 6908 6909
33. M. Presset D. Oehlrich F. Rombouts G. A. Molander Complementary Regioselectivity in Rh(III)-Catalyzed Insertions of Potassium Vinyltrifluoroborate via C-H Activation: Preparation and Use of 4-Trifluoroboratotetrahydroisoquinolones Org. Lett. 2013 15 7 1528 1531
34. A. Nadin C. Hattotuwagama I. Churcher Lead-Oriented Synthesis: A New Opportunity for Synthetic Chemistry Angew. Chem., Int. Ed. 2012 51 5 1114 1122
35. Z. Zhang Y. Yu L. S. Liebeskind N-Amidation by Copper-Mediated Cross-Coupling of Organostannanes or Boronic Acids with O-Acetyl Hydroxamic Acids Org. Lett. 2008 10 14 3005 3008
36. R. D. Farrant J. C. Hollerton S. M. Lynn S. Provera P. J. Sidebottom R. J. Upton NMR quantification using an artificial signal Magn. Reson. Chem. 2010 48 10 753 762