A novel complexity-to-diversity strategy for the diversity-oriented synthesis of structurally diverse and complex macrocycles from quinine

Bioorganic and Medicinal Chemistry

Volumn 25, Issue 11, 2017, Pages 2825-2843

  Ciardiello, J J ^a   Stewart, H L ^a   Sore, H F ^a   Galloway, W R J D ^a   Spring, D R ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Chemical space; Complexity to diversity; Diversity oriented synthesis; Library synthesis; Macrocycles; Natural products; Scaffold

Indexed keywords

3 (ALLYLOXY)BENZALDEHYDE; 3 (AZIDOMETHYL)BENZOIC ACID; 5 (AZIDOMETHYL)FURAN 2 CARBOXYLIC ACID; AMIDE; DIOL; ESTER; ETHYL N [3 (ALLYLOXY)BENZYL] N [2 (THIOPHEN 2 YL)ACETYL]GLYCINATE; ETHYL [3 (ALLYLOXY)BENZYL]GLYCINATE; MACROCYCLIC COMPOUND; METHYL 5 (AZIDOMETHYL)FURAN 2 CARBOXYLATE; METHYL N [2 (4 BROMOPHENYL)ACETYL] N (PROP 2 YN 1 YL)GLYCINATE; METHYL PROP 2 YN 1 YLGLYCINATE; MOLECULAR SCAFFOLD; N [2 (4 BROMOPHENYL)ACETYL] N (PROP 2 YN 1 YL)GLYCINE; QUININE; QUINOTOXINE; UNCLASSIFIED DRUG;

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; PHYSICAL CHEMISTRY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; THIN LAYER CHROMATOGRAPHY; CHEMICAL STRUCTURE; CHEMISTRY;

MACROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; QUININE;

EID: 85014699798     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2017.02.060     Document Type: Article

References (69)

1. 1 Tan, D.S., Foley, M.A., Shair, M.D., Schreiber, S.L., Stereoselective synthesis of over two million compounds having structural features both reminiscent of natural products and compatible with miniaturized cell-based assays. J Am Chem Soc 120:33 (1998), 8565–8566.
2. 2 Galloway, W.R.J.D., Spring, D.R., Is synthesis the main hurdle for the generation of diversity in compound libraries for screening?. Expert Opin Drug Disc 4:5 (2009), 467–472.
3. 3 O'Connell, K.M.G., Galloway, W.R.J.D., Ibbeson, B.M., Isidro-Llobet, A., O'Connor, C.J., Spring, D.R., Diversity-oriented synthesis. Toy, P.H., Lam, W., (eds.) Solid-Phase Organic Synthesis Concepts, Strategies, and Applications, 2012, Wiley, 131–150.
4. 4 Borman, S., Rescueing Combichem. C&EN Sci Technol 82:40 (2004), 32–40.
5. 5 Barnes, E.C., Kumar, R., Davis, R.A., The use of isolated natural products as scaffolds for the generation of chemically diverse screening libraries for drug discovery. Nat Prod Rep 33:3 (2016), 372–381.
6. 6 Grabowski, K., Baringhaus, K.H., Schneider, G., Scaffold diversity of natural products: inspiration for combinatorial library design. Nat Prod Rep 25:5 (2008), 892–904.
7. 7 Maier, M.E., Design and synthesis of analogues of natural products. Org Biomol Chem 13:19 (2015), 5302–5343.
8. 8 Wessjohann, L.A., Synthesis of natural-product-based compound libraries. Curr Opin Chem Biol 4 (2000), 303–309.
9. 9 Feher, M., Schmidt, J.M., Property distributions: differences between drugs, natural products, and molecules from combinatorial chemistry. J Chem Inf Comput Sci 43 (2003), 218–227.
10. 10 Newman, D.J., Cragg, GM, Snader, K.M., Natural Products as Sources of New Drugs over the Period 1981-2002. J Nat Prod 66 (2003), 1022–1037.
11. 11 Rouhi, A.M., Rediscovering Natural Products. C&EN. Science and Technology 81:41 (2003), 77–78.
12. 12 Wessjohann, L.A., Ruijter, E., Strategies for total and diversity-oriented synthesis of natural product (-like) macrocycles. Mulzer, J.H., (eds.) Natural Product Synthesis I: Targets, Methods, Concepts, 2005, Springer-Verlag, Berlin Heidelberg, 137.
13. 13 Henkel, T., Brunne, R.M., Müller, H., Reichel, F., Statistical investigation into the structural complementarity of natural products and synthetic compounds. Angew Chem Int Ed 38:5 (1999), 643–647.
14. 14 Link, A., Active substance development: custom-made needles from combinatoric haystacks. Pharm Ztg 146:43 (2001), 10–16.
15. 15 Newman, D.J., Cragg, G.M., Natural products as sources of new drugs over the 30 years from 1981 to 2010. J Nat Prod 75:3 (2012), 311–335.
16. 16 Camp, D., Garavelas, A., Campitelli, M., Analysis of physicochemical properties for drugs of natural origin. J Nat Prod 78:6 (2015), 1370–1382.
17. 17 Newman, D.J., Cragg, G.M., Natural products as sources of new drugs from 1981–2014. J Nat Prod 79 (2016), 629–661.
18. 18 Fürstner, A., From total synthesis to diverted total synthesis: case studies in the amphidinolide series. Isr J Chem 51 (2011), 329–345.
19. 19 Xu, L.-M., Liang, Y.-F., Ye, Q.-D., Yang, Z., Diversity-oriented syntheses of natural products and natural product-like compounds. Ding, K., Dai, L.-X., (eds.) Organic Chemistry – Breakthroughs and Perspectives, 2012, Wiley-VCH Verlag GmbH & Co, 1–31.
20. 20 Ciardiello, J.J., Galloway, W.R.J.D., O'Connor, C.J., et al. An expedient strategy for the diversity-oriented synthesis of macrocyclic compounds with natural product-like characteristics. Tetrahedron 72:25 (2016), 3567–3578.
21. 21 Morrison, K.C., Hergenrother, P.J., Natural products as starting points for the synthesis of complex and diverse compounds. Nat Prod Rep 31:1 (2014), 6–14.
22. 22 Rizzo, S., Waldmann, H., Development of a natural-product-derived chemical toolbox for modulation of protein function. Chem Rev 114:9 (2014), 4621–4639.
23. 23 Ko, S.K., Jang, H.J., Kim, E., Park, S.B., Concise and diversity-oriented synthesis of novel scaffolds embedded with privileged benzopyran motif. Chem Commun (Camb) 28 (2006), 2962–2964.
24. 24 An, H., Eum, S.-J., Koh, M., Lee, S.K., Park, S.B., Diversity-oriented synthesis of privileged benzopyranyl heterocycles from s-cis-enones. J Org Chem 73 (2008), 1752–1761.
25. 25 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 12 (2010), 548–558.
26. 26 Oh, S., Park, S.B., A design strategy for drug-like polyheterocycles with privileged substructures for discovery of specific small-molecule modulators. Chem Commun (Camb) 47:48 (2011), 12754–12761.
27. 27 Park, S., Srivastava, A., Song, H., Diversity-oriented synthesis of functionalized polyheterocycles from garner aldehyde. Synthesis 14 (2011), 2215–2222.
28. 28 Kim, H., Tung, T.T., Park, S.B., Privileged substructure-based diversity-oriented synthesis pathway for diverse pyrimidine-embedded polyheterocycles. Org Lett 15:22 (2013), 5814–5817.
29. 29 Galloway, W.R.J.D., Stokes, J.E., Spring, D.R., New advances in diversity-oriented synthesis. Czechtizky, W., Hampley, P., (eds.) Small Molecule and Medicinal Chemistry: Strategies and Technologies, 2016, John Wiley & Sons.
30. 30 Huigens, R.W. 3rd, Morrison, K.C., Hicklin, R.W., Flood, T.A. Jr., Richter, M.F., Hergenrother, P.J., A ring-distortion strategy to construct stereochemically complex and structurally diverse compounds from natural products. Nat Chem 5:3 (2013), 195–202.
31. 31 Balthaser, B.R., Maloney, M.C., Beeler, A.B., Porco, J.A., Snyder, J.K., Remodelling of the natural product fumagillol employing a reaction discovery approach. Nat Chem 3:12 (2011), 969–973.
32. 32 Rafferty, R.J., Hicklin, R.W., Maloof, K.A., Hergenrother, P.J., Synthesis of complex and diverse compounds through ring distortion of abietic acid. Angew Chem Int Ed Engl 53:1 (2014), 220–224.
33. 33 Paciaroni, N., Ratnayake, R., Matthews, J., et al. A tryptoline ring distortion strategy leads to complex and diverse biologically active molecules from the indole alkaloid yohimbine. Chemistry, 2016.
34. 34 Krieger, J.P., Ricci, G., Lesuisse, D., Meyer, C., Cossy, J., Efficient and modular synthesis of new structurally diverse functionalized [n]paracyclophanes by a ring-distortion strategy. Angew Chem Int Ed Engl 53:33 (2014), 8705–8708.
35. 35 Rivera, D.G., Pando, O., Bosch, R., Wessjohann, L.A., A biomimetic approach for polyfunctional secocholanes: tuning flexibility and functionality on peptidic and macrocyclic scaffolds derived from bile acids. J Org Chem 73 (2008), 6229–6238.
36. 36 Ricardo, M.G., Morales, F.E., Garay, H., et al. Bidirectional macrocyclization of peptides by double multicomponent reactions. Org Biomol Chem 13:2 (2015), 438–446.
37. 37 Eschenauer, G., DePestel, D.D., Carver, P.L., Comparison of echinocandin antifungals. Ther Clin Risk Manag 3:1 (2007), 71–97.
38. 38 Scheinfeld, N., Telithromycin: a brief review of a new ketolide antibiotic. J Drugs Dermatol 3:4 (2004), 409–413.
39. 39 Wessjohann, L.A., Ruijter, E., Garcia-Rivera, D., Brandt, W., What can a chemist learn from nature's macrocycles?–A brief, conceptual view. Mol Diversity 9 (2005), 171–186.
40. 40 Nicolaou, K.C., Ninkovic, S., Sarabia, F., et al. Total syntheses of epothilones A and B via a macrolactonization-based strategy. J Am Chem Soc. 119 (1997), 7974–7991.
41. 41 O'Connell, K.M., Beckmann, H.S., Laraia, L., et al. A two-directional strategy for the diversity-oriented synthesis of macrocyclic scaffolds. Org Biomol Chem 10:37 (2012), 7545–7551.
42. 42 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 7:7 (2008), 608–624.
43. 43 Mallinson, J., Collins, I., Macrocycles in new drug discovery. Future Med Chem 4:11 (2012), 1409–1438.
44. 44 Marsault, E., Peterson, M.L., Macrocycles are great cycles: applications, opportunities, and challenges of synthetic macrocycles in drug discovery. J Med Chem 54:7 (2011), 1961–2004.
45. 45 Xie, J., Bogliotti, N., Synthesis and applications of carbohydrate-derived macrocyclic scaffolds. Chem Rev 114:15 (2014), 7678–7739.
46. 46 Terrett, N.K., Methods for the synthesis of macrocycle libraries for drug discovery. Drug Discov Today Technol 7:2 (2010), e97–e104.
47. 47 Isidro-Llobet, A., Murillo, T., Bello, P., et al. Diversity-oriented synthesis of macrocyclic peptidomimetics. Proc Natl Acad Sci USA 108:17 (2011), 6793–6798.
48. 48 Delorbe, J.E., Clements, J.H., Whiddon, B.B., Martin, S.F., Thermodynamic and structural effects of macrocyclization as a constraining method in protein-ligand interactions. ACS Med Chem Lett 1:8 (2010), 448–452.
49. 49 Aquino, C., Sarkar, M., Chalmers, M.J., Mendes, K., Kodadek, T., Micalizio, G.C., A biomimetic polyketide-inspired approach to small-molecule ligand discovery. Nat Chem 4:2 (2011), 99–104.
50. 50 Madsen, C.M., Clausen, M.H., Biologically active macrocyclic compounds – from natural products to diversity-oriented synthesis. Eur J Org Chem 2011:17 (2011), 3107–3115.
51. 51 Wells, J.A., McClendon, C.L., Reaching for high-hanging fruit in drug discovery at protein-protein interfaces. Nature 450:7172 (2007), 1001–1009.
52. 52 Cummings, M.D., Lin, T., Tahri, A., et al. Structure-based macrocyclization yields hepatitis C virus NS5B inhibitors with improved binding affinities and pharmacokinetic properties. Angew Chem Int Ed 51 (2012), 4637–4640.
53. 53 Ishii, Y., Fujimoto, R., Mikami, M., Murakami, S., Miki, Y., Furukawa, Y., Practical syntheses of chiral α-amino acids and chiral half-esters by kinetic resolution of urethane-protected α-amino acid n-carboxyanhydrides and desymmetrization of cyclic meso-anhydrides with new modified cinchona alkaloid catalysts. Org Process Res Dev 11:3 (2007), 609–615.
54. 54 Dogo-Isonagie, C., Bekele, T., France, S., et al. Scalable methodology for the catalytic, asymmetric r-bromination of acid chlorides. J Org Chem 71 (2006), 8946–8949.
55. 55 Zhang, T., He, W., Zhao, X., Jin, Y., Asymmetric oxaziridination catalyzed by cinchona alkaloid derivatives containing sulfide. Tetrahedron 69:35 (2013), 7416–7422.
56. 56 Sanders, N.G., Meyers, D.J., Sullivan, D.J., Antimalarial efficacy of hydroxyethylapoquinine (SN-119) and its derivatives. Antimicrob Agents Chemother 58:2 (2014), 820–827.
57. 57 Zhao, M.-X., Tang, W.-H., Chen, M.-X., Wei, D.-K., Dai, T.-L., Shi, M., Highly enantioselective Michael addition of 3-aryloxindoles to phenyl vinyl sulfone catalyzed by cinchona alkaloid-derived bifunctional amine-thiourea catalysts bearing sulfonamide as multiple hydrogen-bonding donors. Eur J Org Chem 2011:30 (2011), 6078–6084.
58. 58 Dinio, T., Gorka, A.P., McGinniss, A., Roepe, P.D., Morgan, J.B., Investigating the activity of quinine analogues versus chloroquine resistant Plasmodium falciparum. Bioorg Med Chem 20:10 (2012), 3292–3297.
59. 59 Rowan, S.J., Brady, P.A., Sanders, J.K.M., Structure-directed synthesis under thermodynamic control: macrocyclic trimers from cinchona alkaloids. Angew Chem Int Ed 35:18 (1996), 2143–2145.
60. 60 Debarge, S., Thibaudeau, S., Violeau, B., et al. Rearrangement or gem-difluorination of quinine and 9-epiquinine and their acetates in superacid. Tetrahedron 61:8 (2005), 2065–2073.
61. 61 Abdel-Magid, A.F., Carson, K.G., Harris, B.D., Maryanoff, C.A., Shah, R.D., Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures. J Org Chem 61 (1996), 3849–3862.
62. 62 Beckmann, H.S., Nie, F., Hagerman, C.E., et al. A strategy for the diversity-oriented synthesis of macrocyclic scaffolds using multidimensional coupling. Nat Chem 5:10 (2013), 861–867.
63. 63 Schawrz, M.K., Sauer, W.H.B., Molecular shape diversity of combinatorial libraries: a prerequisite for broad bioactivity. J Chem Inf Comput Sci 43 (2003), 987–1003.
64. 64 Galloway, W.R., Isidro-Llobet, A., Spring, D.R., Diversity-oriented synthesis as a tool for the discovery of novel biologically active small molecules. Nat Commun, 2010, 1–80.
65. 65 Isidro-Llobet, A., Hadje Georgiou, K., Galloway, W.R.J.D., et al. Spring DROBC, 13,4570. A diversity-oriented synthesis strategy enabling the combinatorial-type variation of macrocyclic peptidomimetic scaffolds. Org Biomol Chem 13 (2015), 4570–4580.
66. 66 Memeo MG. University of Cambridge, 2012.
67. 67 Khalil, N.S.A.M., Efficient synthesis of novel 1,2,4-trazole fused acyclic and 21–28 membered macrocyclic and/or lariat macrocyclic oxaazathia crown compounds with potential microbial activity. Eur J Med Chem 45:11 (2010), 5265–5277.
68. 68 Walker, D.P., Wishka, D.G., Beagley, P., Turner, G., Solesbury, N., Synthesis of (±)-8-oxa-3-azabicyclo[3.2.1]octan-2-thione and (±)-2-oxa-5-azabicyclo[2.2.1]heptan-6-thione: potential synthons for the preparation of novel heteroaryl-annulated bicyclic morpholines. Synthesis 7 (2011), 1113–1119.
69. 69 Struthers, H., Spingler, B., Mindt, T.L., Schibli, R., “Click-to-Chelate”: Design and incorporation of triazole-containing metal-chelating systems into biomolecules of diagnostic and therapeutic interest. Chem Eur J 14 (2008), 6173–6183.