Natural product-like synthetic libraries

Current Opinion in Chemical Biology

Volumn 15, Issue 4, 2011, Pages 516-522

  Thomas, Gemma L ^a   Johannes, Charles W ^a  

^a INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTINE; ERIBULIN; FURANODICIN; NATURAL PRODUCT; UNCLASSIFIED DRUG;

DRUG INDUSTRY; DRUG QUALITY; DRUG RESEARCH; DRUG STRUCTURE; PROTEIN PROTEIN INTERACTION; REVIEW; STEREOCHEMISTRY; SYNTHETIC BIOLOGY;

BIOLOGICAL AGENTS; BIOLOGICAL FACTORS; COMBINATORIAL CHEMISTRY TECHNIQUES; DATABASES, FACTUAL; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; HUMANS; MOLECULAR STRUCTURE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SMALL MOLECULE LIBRARIES;

EID: 79961012396     PISSN: 13675931     EISSN: 18790402     Source Type: Journal    
DOI: 10.1016/j.cbpa.2011.05.022     Document Type: Review

References (46)

1. Rishton G.M. Molecular diversity in the context of leadlikeness: compound properties that enable effective biochemical screening. Curr Opin Chem Biol 2008, 12:340-351.
2. Jacoby E., Mozzarelli A. Chemogenomic strategies to expand the bioactive chemical space. Curr Med Chem 2009, 16:4374-4381.
3. Lipinski C.A., Lombardo F., Bominy B.W., Feeney P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Del Rev 1997, 23:3-25.
4. Veber D.F., Johnson S.R., Cheng H.Y., Smith B.R., Ward K.W., Kopple K.D. Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem 2002, 45:2615-2623.
5. Newman D.J., Craig G.M., Snader K.M. Natural products as sources for new drugs over the period 1981-2002. J Nat Prod 2003, 66:1022-1037.
6. Harvey A.L. Natural products in drug discovery. Drug Dis Today 2008, 13:894-901.
7. Dancik V., Seiler P., Young D.W., Schrebier S.L., Clemons P.A. Distinct biological network properties between the targets of natural products and disease genes. J Am Chem Soc 2010, 132:9259-9261.
8. Hajduk P.J., Galloway W.R.J.D., Spring D.R. A question of library design. Nature 2011, 470:42-43.
9. Welsch M.E., Snyder S.A., Stockwell B.R. Privileged scaffolds for library design and drug discovery. Curr Opin Drug Dis 2010, 14:347-361.
10. Kumar K., Wladman H. Synthesis of natural product inspired compound collections. Angew Chem Int Ed 2009, 48:3224-3242.
11. Lovering F., Bikker J., Humblet C. Escape from flatland: increasing saturation as an approach to improving clinical success. J Med Chem 2009, 52:6752-6756.
12. Bauer R.A., Wurst J.M., Tan D.S. Expanding the range of druggable targets with natural product-based libraries: an academic perspective. Curr Opin Chem Biol 2010, 14:308-314.
13. Dandapani S., Marcaurelle L.A. Current strategies for diversity oriented synthesis. Curr Opin Chem Biol 2010, 14:362-370.
14. Wilk W., Zimmermann T.J., Kaiser M., Waldman H. Principles, implementation, and application of biology-oriented synthesis (Bios). Biol Chem 2010, 391:491-497.
15. Kombarov R., Altieri A., Genis D., Kirpichenok M., Kochubey V., Rakitina N., Titarenko Z. BioCores: identification of a drug/natural product based privileged structural motif for small-molecule lead discovery. Mol Dis 2010, 14:193-200.
16. Wender P.A., Verma V.A., Paxton T.J., Pillow T.H. Function-oriented synthesis, step economy, and drug design. Accounts Chem Res 2008, 41:40-49.
17. Wilson R.M., Danishefsky S.J. Small molecule natural products in the discovery of therapeutic agents: the synthesis connection. J Org Chem 2006, 71:8329-8351.
18. Feher M., Schmidt J.M. Property distributions: differences between drugs, natural prod and molecules from combinatorial chemistry. J Chem Inf Comput Sci 2003, 43:218-227.
19. Ledford H. Complex synthesis yields breast-cancer therapy. Nature 2010, 468:608-609.
20. Chellappan S.K., Xiao Y., Tueckmantel W., Kellar K.J., Kozikowski A.P. Synthesis and pharmacological evaluation of novel 9- and 10-substituted cytosine derivatives. Nicotinic ligands of enhanced subtype selectivity. J Med Chem 2006, 49:2673-2676.
21. Ogata M., Hattori T., Takeuchi R., Usui T. Novel and facile synthesis of furanodictines A and B based on transformation of 2-acetamido-2-deoxy-d-glucose into 3,6-anhydro hexafuranoses. Carbohydr Res 2010, 345:230-234.
22. Kikuchi H., Saito Y., Komiya J., Takaya Y., Honma S., Nakahata N., Ito A., Oshima Y. Furanodictine A and B: amino sugar analogues produced by cellular slime mold Dictyostelium discoideum showing neuronal differentiation activity. J Org Chem 2001, 66:6982-6987.
23. Morton D., Leach S., Cordier C., Warriner S., Nelson A. Synthesis of natural-product-like molecules with over eighty distinct scaffolds. Angew Chem Int Ed 2008, 48:104-109.
24. Burke M.B., Schrieber S.L. A planning strategy for Diversity-Oriented Synthesis. Angew Chem Int Ed 2008, 43:46-58.
25. Comer E., Rohan E., Deng L., Porco J.A. An approach to skeletal diversity using functional group pairing of multifunctional scaffolds. Org Lett 2007, 9:2123-2126.
26. Singh S.B., Culberson C. Chemical space and the difference between natural products and synthetics. Nat Prod Chem Drug Dis 2010, 18:28-43.
27. Driggers E.M., Hale S.P., Lee J., Terrett N.K. The exploration of macrocycles for drug discovery - an underexploited structural class. Nat Rev Drug Disc 2008, 7:608-624.
28. Peng L.F., Stanton B.Z., Maloof N., Wang X., Schreiber S.L. Synthesis of aminoalcohol-derived macrocycles leading to a small-molecule binder to an inhibitor of Sonic Hedgehog. Bioorg Med Chem Lett 2009, 19:6319-6325.
29. Burke M.D., Berger E.M., Schreiber S.L. A synthesis strategy yielding skeletally diverse small molecules combinatorially. J Am Chem Soc 2004, 126:14095-14104.
30. Marcaurelle L.A., Comer E., Dandapani S., Duvall J.R., Garard B., Kesavan S., Lee M.D., Liu H., Lowe J.T., Marie J.C., 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 2010, 132:16962-16976.
31. Pizzirani D., Kaya T., Clemons P.A., Schreiber S.L. Stereochemical and skeletal diversity arising from amino propargylic alcohols. Org Lett 2010, 12:2822-2825.
32. Bauer R.A., DiBlasi C.M., Tan D.S. The tert-butylsulfinamide lynchpin in transition-metal-mediated multiscaffold library synthesis. Org Lett 2010, 12:2084-2087.
33. Horton D.A., Bourne G.T., Smythe M.L. The combinatorial synthesis of bicyclic privileged structures or privileged substructures. Chem Rev 2003, 103:893-930.
34. Li D., Duan S., Hu Y. Three-component one-pot approach to synthesize benzopyrano[4,3-d]pyrimidines. J Comb Chem 2010, 12:895-899.
35. Oh S., Jang H.J., Ko S.K., Ko Y., Park S.B. Construction of a polyheterocyclic benzopyran library with diverse core skeletons through Diversity-Oriented Synthesis Pathway. J Comb Chem 2010, 12:548-558.
36. Kumar A., Srivastava S., Gupta G., Chaturvedi V., Sinha S., Srivastava R. Natural product inspired diversity oriented synthesis of tetrahydroquinline scaffolds as antitubercular agent. ACS Comb Sci 2010, 13:65-71.
37. Kumar A., Sharma S., Maurya R.A., Sarkar J. Diversity oriented synthesis of benzoxanthene and benzochromene libraries via one-pot, three-component reactions and their anti-proliferative activity. J Comb Chem 2010, 12:20-24.
38. Cheng C., Pan L., Chen Y., Song H., Qin Y., Li R. Total synthesis of (±)-Marinopyrrole A and its library as potential antibiotic and anticancer agents. J Comb Chem 2010, 12:541-547.
39. Nodwell M., Zimmerman C., Roberge M., Andersen R.J. Synthetic analogues of the microtubule-stabilizing sponge alkaloid Ceratamine A are more active than the natural product. J Med Chem 2010, 53:7843-7851.
40. Marcaurelle L.A., Johannes C., Yohannes D., Tillotson B.P., Mann D. Diversity-oriented synthesis of a cytisine-inspired pyridone library leading to the discovery of novel inhibitor of Bcl-2. Bioorg Med Chem Lett 2009, 19:2500-2503.
41. Drewry D.H., Macarron R. Enhancements of screening collections to address areas of unmet medical need: an industry perspective. Curr Opin Chem Biol 2010, 14:289-298.
42. Dandapani S., Marcaurelle L.A. Current strategies for diversity-oriented synthesis. Curr Opin Chem Biol 2010, 14:362-370.
43. Johannes C.W., Marcaurelle L.A. Application of natural product inspired diversity-oriented synthesis to drug discovery. Prog Drug Res Nat Prod Drugs 2008, 2:188-216.
44. Castro C U.S. Patent Application No. 11/842,581, 2008.
45. Hanessian S. Total Synthesis of Natural Products: The 'Chiron' Approach 1983, Pergamon, Oxford, UK. J.E. Baldwin (Ed.).
46. Abbenante G., Becker B., Blanc S., Clark C., Condie G., Fraser G., Grathwohl M., Halliday J., Henderson S., Lam A., et al. Biological diversity from a structurally diverse library: systematically scanning conformational space using a pyranose scaffold. J Med Chem 2010, 53:5576-5586.