Natural products as lead structures: Chemical transformations to create lead-like libraries

Drug Discovery Today

Volumn 19, Issue 3, 2014, Pages 215-221

  Pascolutti, Mauro ^a   Quinn, Ronald J ^a  

^a GRIFFITH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHECULARIN; ARTEMISININ; LEAD; NATURAL PRODUCT; QUINONE DERIVATIVE; SESQUITERPENE; UNCLASSIFIED DRUG; BIOLOGICAL PRODUCT; MOLECULAR LIBRARY;

CHEMICAL STRUCTURE; HUMAN; HYDROGEN BOND; MOLECULAR LIBRARY; MOLECULAR WEIGHT; PARTITION COEFFICIENT; PHYSICAL CHEMISTRY; REVIEW; CHEMISTRY; DRUG DESIGN; MEDICINAL CHEMISTRY;

BIOLOGICAL PRODUCTS; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; HUMANS; MOLECULAR WEIGHT; SMALL MOLECULE LIBRARIES;

EID: 84896402409     PISSN: 13596446     EISSN: 18785832     Source Type: Journal    
DOI: 10.1016/j.drudis.2013.10.013     Document Type: Short Survey

References (60)

1. D.J. Newman, and G.M. Cragg Natural products as sources of new drugs over the 30 years from 1981 to 2010 J. Nat. Prod. 75 2012 311 335
2. M. Feher, and J.M. Schmidt Property distributions: differences between drugs, natural products, and molecules from combinatorial chemistry J. Chem. Inf. Comput. Sci. 43 2003 218 227
3. K. Grabowski, and G. Schneider Properties and architecture of drugs and natural products revisited Curr. Chem. Biol. 1 2007 115 127
4. A. Ganesan The impact of natural products upon modern drug discovery Curr. Opin. Chem. Biol. 12 2008 306 317
5. J. Rosén et al. Novel chemical space exploration via natural products J. Med. Chem. 52 2009 1953 1962
6. J. Hert et al. Quantifying biogenic bias in screening libraries Nat. Chem. Biol. 5 2009 479 483
7. R. Breinbauer et al. From protein domains to drug candidate: natural products as guiding principles in the design and synthesis of compound libraries Angew. Chem. 41 2002 2878 2890 (Pubitemid 34966550)
8. L. Eberhardt et al. Exploring and exploiting biologically relevant chemical space Curr. Drug Targets 12 2011 1531 1546
9. E. Kellenberger et al. Similar interactions of natural products with biosynthetic enzymes and therapeutic targets could explain why nature produces such a large proportion of existing drugs Nat. Prod. Rep. 28 2011 1483 1492
10. F.E. Koehn, and G.T. Carter The evolving role of natural products in drug discovery Nat. Rev. Drug Discov. 4 2005 206 220 (Pubitemid 40372555)
11. A.L. Harvey Natural products in drug discovery Drug Discov. Today 13 2008 894 901
12. J.W.-H. Li, and J.C. Vederas Drug discovery and natural products: end of an era or an endless frontier? Science 325 2009 161 165
13. J.-Y. Ortholand, and A. Ganesan Natural products and combinatorial chemistry: back to the future Curr. Opin. Chem. Biol. 8 2004 271 280 (Pubitemid 38759402)
14. S.L. Schreiber Target-oriented and diversity-oriented organic synthesis in drug discovery Science 287 2000 1964 1969 (Pubitemid 30158663)
15. M.D. Burke, and G. Lalic Teaching target-oriented and diversity-oriented organic synthesis at Harvard University Chem. Biol. 9 2002 535 541 (Pubitemid 34593033)
16. D.S. Tan Diversity-oriented synthesis: exploring the intersections between chemistry and biology Nat. Chem. Biol. 1 2005 74 84
17. A. Nören-Müller et al. Discovery of protein phosphatase inhibitor classes by biology-oriented synthesis Proc. Natl. Acad. Sci. U. S. A. 103 2006 10606 10611 (Pubitemid 44078024)
18. S. Wetzel et al. Biology-oriented synthesis Angew. Chem. 50 2011 10800 10826
19. P.A. Wender et al. Function-oriented synthesis, step economy, and drug design Acc. Chem. Res. 41 2007 40 49
20. C.A. Lipinski et al. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Deliv. Rev. 23 1997 3 25 (Pubitemid 27046991)
21. G.R. Bickerton et al. Quantifying the chemical beauty of drugs Nat. Chem. 4 2012 90 98
22. P. Leeson Drug discovery: chemical beauty contest Nature 481 2012 455 456
23. 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)
24. S.J. Teague et al. The design of leadlike combinatorial libraries Angew. Chem. 38 1999 3743 3748 (Pubitemid 30022004)
25. 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
26. M.M. Hann, and T.I. Oprea Pursuing the leadlikeness concept in pharmaceutical research Curr. Opin. Chem. Biol. 8 2004 255 263 (Pubitemid 38759400)
27. P.D. Leeson, and A.M. Davis Time-related differences in the physical property profiles of oral drugs J. Med. Chem. 47 2004 6338 6348 (Pubitemid 39587257)
28. J.A. Lumley Compound selection and filtering in library design QSAR Comb. Sci. 24 2005 1066 1075 (Pubitemid 41736472)
29. A.M. Davis et al. Components of successful lead generation Curr. Top. Med. Chem. 5 2005 421 439 (Pubitemid 40753878)
30. H. Verheij Leadlikeness and structural diversity of synthetic screening libraries Mol. Div. 10 2006 377 388 (Pubitemid 44546689)
31. I. Collins, and P. Workman New approaches to molecular cancer therapeutics Nat. Chem. Biol. 2 2006 689 700 (Pubitemid 44764211)
32. T. Oprea et al. Lead-like, drug-like or 'Pub-like': how different are they? J. Comput. Aided Mol. Des. 21 2007 113 119 (Pubitemid 46416670)
33. R. Brenk et al. Lessons learnt from assembling screening libraries for drug discovery for neglected diseases ChemMedChem 3 2008 435 444
34. G.M. Keseru, and G.M. Makara The influence of lead discovery strategies on the properties of drug candidates Nat. Rev. Drug Discov. 8 2009 203 212
35. S.M. Khersonsky, and Y.-T. Chang Forward chemical genetics: library scaffold design Comb. Chem. High Throughput Screen. 7 2004 645 652 (Pubitemid 39371212)
36. I.D. Jenkins et al. Synthesis of four novel natural product inspired scaffolds for drug discovery J. Org. Chem. 74 2008 1304 1313
37. D.R. Dragoli et al. Parallel synthesis of prostaglandin E1 analogues J. Comb. Chem. 1 1999 534 539
38. K.C. Nicolaou et al. Natural product-like combinatorial libraries based on privileged structures. 1. General principles and solid-phase synthesis of benzopyrans J. Am. Chem. Soc. 122 2000 9939 9953
39. A.M. Boldi et al. Solid-phase library synthesis of alkoxyprolines J. Comb. Chem. 3 2001 367 373 (Pubitemid 33614515)
40. M.C. Pirrung et al. Synthesis of 2,5-dihydroxy-3-(indol-3-yl) benzoquinones by acid-catalysed condensation of indoles with 2,5-dichlorobenzoquinone J. Org. Chem. 67 2002 8374 8388 (Pubitemid 35402983)
41. A.G. Myers, and B.A. Lanman A solid-supported, enantioselective synthesis suitable for the rapid preparation of large numbers of diverse structural analogues of (-)-saframycin A J. Am. Chem. Soc. 124 2002 12969 12971 (Pubitemid 35247107)
42. D.R. Spring et al. Diversity-oriented synthesis of biaryl-containing medium rings using a one bead/one stock solution platform J. Am. Chem. Soc. 124 2002 1354 1363 (Pubitemid 34169142)
43. W. Zhang et al. Solution-phase preparation of a 560-compound library of individual pure mappicine analogues by fluorous mixture synthesis J. Am. Chem. Soc. 124 2002 10443 10450 (Pubitemid 34977397)
44. L. Kissau et al. Development of natural product-derived receptor tyrosine kinase inhibitors based on conservation of protein domain fold J. Med. Chem. 46 2003 2917 2931 (Pubitemid 36775917)
45. Y. Liao et al. Diversity oriented synthesis and branching reaction pathway to generate natural product-like compounds Curr. Med. Chem. 10 2003 2285 2316 (Pubitemid 37236387)
46. M.C. Pirrung, and H. Liu Modular, parallel synthesis of an illudinoid combinatorial library Org. Lett. 5 2003 1983 1985 (Pubitemid 37161974)
47. O. Barun et al. Natural product-guided synthesis of a spiroacetal collection reveals modulators of tubulin cytoskeleton integrity Eur. J. Org. Chem. 2005 2005 4773 4788 (Pubitemid 41659441)
48. C. Mang et al. Natural products in combinatorial chemistry: an andrographolide-based library J. Comb. Chem. 8 2006 268 274 (Pubitemid 43503936)
49. S.-C. Lee, and S.B. Park Solid-phase parallel synthesis of natural product-like diaza-bridged heterocycles through Pictet-Spengler intramolecular cyclization J. Comb. Chem. 8 2006 50 57 (Pubitemid 43166081)
50. S. Su, and J.A. Porco Synthesis of pyrrolo-isoquinolines related to the lamellarins using silver-catalysed cycloisomerization/dipolar cycloaddition J. Am. Chem. Soc. 129 2007 7744 7745 (Pubitemid 46998159)
51. C.S. Mizuno et al. Design, synthesis, biological evaluation and docking studies of pterostilbene analogs inside PPARα Bioorg. Med. Chem. 16 2008 3800 3808 (Pubitemid 351484033)
52. S. Barluenga et al. Divergent synthesis of a pochonin library targeting HSP90 and in vivo efficacy of an identified inhibitor Angew. Chem. 47 2008 4432 4435
53. A. Nören-Müller et al. Discovery of a new class of inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase b by biology-oriented synthesis Angew. Chem. 47 2008 5973 5977
54. S. Amslinger, and S.K. Lindner Limno-CP: a natural-product-inspired 5-aryl-3(2H)-furanone as scaffold for a library of α-modified enones Synthesis 16 2011 2671 2683
55. H. Oguri et al. Generation of anti-trypanosomal agents through concise synthesis and structural diversification of sesquiterpene analogues J. Am. Chem. Soc. 133 2011 7096 7105
56. L.A. Smyth et al. Design and evaluation of 3-aminopyrazolopyridinone kinase inhibitors inspired by the natural product indirubin Bioorg. Med. Chem. 19 2011 3569 3578
57. G. Viault et al. Synthesis of a focused chemical library based on derivatives of embelin, a natural product with proapoptotic and anticancer properties Eur. J. Org. Chem. 2011 2011 1233 1241
58. E.C. Barnes et al. Design and synthesis of screening libraries based on the muurolane natural product scaffold Org. Biomol. Chem. 10 2012 4015 4023
59. V.R. Rao et al. Synthesis and biological evaluation of new piplartine analogues as potent aldose reductase inhibitors (ARIs) Eur. J. Med. Chem. 57 2012 344 361
60. C. Dockendorff et al. Macrocyclic Hedgehog pathway inhibitors: optimization of cellular activity and mode of action studies ACS Med. Chem. Lett. 3 2012 808 813