Towards the realisation of lead-oriented synthesis

Drug Discovery Today

Volumn 19, Issue 7, 2014, Pages 813-819

  Doveston, Richard ^a   Marsden, Stephen ^a   Nelson, Adam ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BROMIDE; IMIDE; LEAD; MOLECULAR SCAFFOLD; PALLADIUM; TRICHLOROACETIMIDIC ACID;

AMINATION; CATALYSIS; CENTRAL NERVOUS SYSTEM; CONCEPTUAL FRAMEWORK; DRUG DEVELOPMENT; LIPOPHILICITY; MOLECULAR SIZE; MOLECULAR WEIGHT; REVIEW; RING CLOSING METATHESIS; SYNTHESIS; ANIMAL; COMBINATORIAL CHEMISTRY; HUMAN; PROCEDURES; TRENDS;

ANIMALS; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DISCOVERY; HUMANS;

EID: 84903795444     PISSN: 13596446     EISSN: 18785832     Source Type: Journal    
DOI: 10.1016/j.drudis.2013.11.006     Document Type: Short Survey

References (40)

1. M.C. Wenlock et al. A comparison of physiochemical property profiles of development and marketed oral drugs J. Med. Chem. 46 2003 1250 1256 (Pubitemid 36428230)
2. P.D. Leeson, and B. Springthorpe The influence of drug-like concepts on decision-making in medicinal chemistry Nat. Rev. Drug Discov. 6 2007 881 890 (Pubitemid 350042396)
3. T.J. Ritchie, and S.J.F. Macdonald The impact of aromatic ring count on compound developability - are too many aromatic rings a liability in drug design? Drug Discov. Today 14 2009 1011 1020
4. F. Lovering et al. Escape from Flatland: increasing saturation as an approach to improving clinical success J. Med. Chem. 52 2009 6752 6756
5. T.I. Oprea et al. Is there a difference between leads and drugs? A historical perspective J. Chem. Inf. Comput. Sci. 41 2001 1308 1315
6. G.M. Keserü, and G.M. Makara The influence of lead discovery strategies on the properties of drug candidates Nat. Rev. Drug Discov. 8 2009 203 212
7. A. Nadin et al. Lead-oriented synthesis: a new opportunity for synthetic chemistry Angew. Chem. Int. Ed. 51 2012 1114 1122
8. A.H. Lipkus et al. Structural diversity of organic chemistry. A scaffold analysis of the CAS registry J. Org. Chem. 73 2008 4443 4451 (Pubitemid 351842458)
9. A.A. Shelat, and R.K. Guy Scaffold composition and biological relevance of screening libraries Nat. Chem. Biol. 3 2007 442 446 (Pubitemid 47080378)
10. M. Krier et al. Assessing the scaffold diversity of screening libraries J. Chem. Inf. Model. 46 2006 512 524
11. S.D. Roughley, and A.M. Jordan The medicinal chemist's toolbox: an analysis of reactions used in the pursuit of drug candidates J. Med. Chem. 54 2011 3451 3479
12. T.W.J. Cooper et al. Factors determining the selection of organic reactions by medicinal chemists and the use of these reactions in arrays (small focused libraries) Angew. Chem. Int. Ed. 49 2010 8082 8091
13. H. Wild et al. The importance of chemistry for the future of the pharma industry Angew. Chem. Int. Ed. 50 2011 7452 7453
14. M. Dow et al. Towards the systematic exploration of chemical space Org. Biomol. Chem. 10 2012 17 28
15. T.E. Nielsen, and S.L. Schreiber Towards the optimal screening collection: a synthesis strategy Angew. Chem. Int. Ed. 47 2008 48 56
16. M.D. Burke, and S.L. Schreiber A planning strategy for diversity-oriented synthesis Angew. Chem. Int. Ed. 43 2004 46 56
17. W.R.J.D. Galloway et al. Diversity-oriented synthesis as a tool for the discovery of novel biologically active small molecules Nat. Commun. 1 2010 80
18. J.T. Lowe et al. Synthesis of profiling of a diverse collection of azetidine-based scaffolds for the development of CNS-focused lead-like libraries J. Org. Chem. 77 2012 7187 7211
19. A.W. Hung et al. Route to three-dimensional fragments using diversity-oriented synthesis Proc. Natl. Acad. Sci. U. S. A. 108 2011 6799 6804
20. D. Robbins et al. Synthesis of natural-product-like scaffolds in unprecedented efficiency via a 12-fold branching pathway Chem. Sci. 2 2011 2232 2235
21. N. Kumagai et al. Short synthesis of skeletally and stereochemically diverse small molecules by coupling Petasis condensation reactions to cyclization reactions Angew. Chem. Int. Ed. 45 2006 3635 3638 (Pubitemid 44105728)
22. H. Oguri, and S.L. Schreiber Skeletal diversity via a folding pathway: synthesis of indole alkaloid-like skeletons Org. Lett. 7 2005 47 50 (Pubitemid 40138308)
23. M.D. Burke et al. A synthesis strategy yielding skeletally diverse small molecules combinatorially J. Am. Chem. Soc. 126 2004 14095 14104 (Pubitemid 39447088)
24. D. Morton et al. Synthesis of natural-product-like molecules with over eighty distinct scaffolds Angew. Chem. Int. Ed. 48 2009 104 109
25. L.A. Marcaurelle et al. An aldol-based build/couple/pair strategy for the synthesis of medium- and large-sized rings: discovery of macrocyclic histone deacetylase inhibitors J. Am. Chem. Soc. 132 2010 16962 16976
26. R.A. Brawn et al. An efficient synthesis of bridged heterocycles from an Ir(I) bis-amination/ring-closing metathesis sequence Org. Lett. 14 2012 4802 4805
27. P. MacLellan, and A. Nelson A conceptual framework for analysing and planning synthetic approaches to diverse lead-like scaffolds Chem. Commun. 49 2013 2383 2393
28. J.S. Nakhla et al. Palladium-catalyzed alkene carboamination reactions for the synthesis of substituted piperazines Tetrahedron 65 2009 6549 6570
29. M.B. Bertrand et al. Mild conditions for the synthesis of functionalized pyrrolidines via Pd-catalyzed carboamination reactions Org. Lett. 9 2007 457 460
30. M.B. Bertrand et al. Mild conditions for Pd-catalyzed carboamination of N-protected hex-4-enylamines and 1-, 3-, and 4-substituted pent-4-enylamines. Scope, limitations, and mechanism of pyrrolidine formation J. Org. Chem. 73 2008 8851 8860
31. M.L. Leathen et al. New strategy for the synthesis of substituted morpholines J. Org. Chem. 74 2009 5107 5110
32. J.E. Ney, and J.P. Wolfe Selective synthesis of 5- or 6-aryl octahydrocyclopenta[b]pyrroles from a common precursor through control of competing pathways in a Pd-catalyzed reaction J. Am. Chem. Soc. 127 2005 8644 8651 (Pubitemid 40868246)
33. D.M. Schultz, and J.P. Wolfe Intramolecular alkene carboamination reactions for the synthesis of enantiomerically enriched tropane derivatives Org. Lett. 13 2011 2962 2965
34. A. Rolfe et al. Formal [4 + 3] epoxide cascade reaction via a complementary ambiphilic pairing strategy Org. Lett. 12 2010 1216 1219
35. J. Horn et al. Convergent, regiospecific synthesis of quinolines from o-aminophenylboronates Org. Lett. 10 2008 4117 4120
36. J. Horn et al. Convergent synthesis of dihydroquinolones from o-aminoarylboronates Tetrahedron 65 2009 9002 9007
37. A. Klapars et al. Synthesis of medium ring nitrogen heterocycles via a tandem copper-catalyzed CN bond formation-ring-expansion process J. Am. Chem. Soc. 126 2004 3529 3533 (Pubitemid 38366742)
38. J. Zhou et al. Multicomponent approach in the synthesis of 2,2,6-trisubstituted morpholine derivatives Org. Lett. 14 2012 5250 5253
39. C. O'Leary-Steele et al. Synthesis of small molecules with high scaffold diversity: exploitation of metathesis cascades in combination with inter- and intramolecular Diels-Alder reactions Chem. Eur. J. 16 2010 9563 9571
40. S.M. Paul et al. How to improve R&D productivity: the pharmaceutical industry's grand challenge Nat. Rev. Drug Discov. 9 2010 203 214