Creation and manipulation of common functional groups en route to a skeletally diverse chemical library

Proceedings of the National Academy of Sciences of the United States of America

Volumn 108, Issue 17, 2011, Pages 6763-6768

  Cui, Jiayue ^a   Hao, Jason ^a   Ulanovskaya, Olesya A ^a   Dundas, Joseph ^a,b   Liang, Jie ^a,b   Kozmin, Sergey A ^a  

^a UNIVERSITY OF CHICAGO   (United States)

^b University of Illinois at Chicago   (United States)

Author keywords

Diversity oriented synthesis; Glycolysis; Skeletal diversity

Indexed keywords

ADENOSINE TRIPHOSPHATE; ALKENE; CHEMICAL COMPOUND;

ANIMAL CELL; ARTICLE; BIOLOGICAL ACTIVITY; CARBAMOYLATION; CHEMICAL ANALYSIS; CHEMICAL STRESS; CHO CELL; CHO K1 CELL; CONTROLLED STUDY; CYCLOADDITION; GLYCOLYSIS; ISOMERIZATION; MOLECULAR LIBRARY; MOLECULE; NONHUMAN; PRIORITY JOURNAL; SYNTHESIS;

ADENOSINE TRIPHOSPHATE; ANIMALS; CHO CELLS; CRICETINAE; CRICETULUS; GLYCOLYSIS; HETEROCYCLIC COMPOUNDS, 3-RING;

EID: 79955557935     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1015253108     Document Type: Article

References (36)

1. Stockwell BR (2000) Chemical genetics: Ligand-based discovery of gene function. Nat Rev Genet 1:116-125.
2. Bredel M, Jacoby E (2004) Chemogenomics: An emerging strategy for rapid target and drug discovery. Nat Rev Genet 5:262-275. (Pubitemid 38435622)
3. Burke MD, Schreiber SL (2004) A planning strategy for diversity-oriented synthesis. Angew Chem Int Edit 43:46-58. (Pubitemid 38063470)
4. Aubert C, Buisine O, Malacria M (2002) The behavior of 1,n-enynes in the presence of transition metals. Chem Rev 102:813-834. (Pubitemid 35377615)
5. Zhang L, Sun J, Kozmin S (2006) Gold and platinum catalysis of enyne cycloisomerization. Adv Synth Catal 348:2271-2296. (Pubitemid 44865607)
6. Michelet V, Toullec P, Genêt JP (2008) Cycloisomerization of 1,n-enynes: challenging metal-catalyzed rearrangements and mechanistic insights. Angew Chem Int Edit 47:4268-4315.
7. Schramm MP, Reddy DS, Kozmin SA (2001) Siloxyalkyne-alkene metathesis: Rapid access to highly functionalized enones. Angew Chem Int Edit 40:4274-4277.
8. Zhang L, Kozmin SA (2004) Gold-catalyzed cycloisomerizations of siloxy enynes to cyclohexadienes. J Am Chem Soc 126:11806-11807. (Pubitemid 39298325)
9. Zhang L, Kozmin SA (2005) Gold-catalyzed assembly of heterobicyclic systems. J Am Chem Soc 127:6962-6963. (Pubitemid 40676719)
10. Sun J, Conley MP, Zhang L, Kozmin SA (2006) Gold and platinum-catalyzed cycloisomerizations of 1,5-enynes to cyclohexadienes with a broad alkyne scope. J Am Chem Soc 128:9705-9710. (Pubitemid 44147954)
11. Micalizio GC, Schreiber SL (2002) A boronic ester annulation strategy for diversity-oriented organic synthesis. Angew Chem Int Edit 41:152-154. (Pubitemid 34076129)
12. Spiegel DA, Schroeder FC, Duvall JR, Schreiber SL (2006) An oligomer-based approach to skeletal diversity in small molecule synthesis. J Am Chem Soc 128:14766-14767. (Pubitemid 44851590)
13. Kumagai N, Muncipinto G, Schreiber SL (2006) Short synthesis of skeletally and stereo-chemically diverse small molecules by coupling petasis condensation reactions to cyclization reactions. Angew Chem Int Edit 45:3635-3638. (Pubitemid 44105728)
14. Luo T, Schreiber SL (2009) Gold(I)-catalyzed coupling reactions for the synthesis of diverse small molecules using the build/couple/pair strategy. J Am Chem Soc 131:5667-5674.
15. Pizzirani D, Kaya T, Clemons PA, Schreiber SL (2010) Stereochemical and skeletal diversity arising from amino propargylic alcohols. Org Lett 12:2822-2825.
16. Brummond KM, Mitasev B (2004) Allenes and transition metals: A diverging approach to heterocycles. Org Lett 6:2245-2248. (Pubitemid 38918710)
17. Brummond KM, Mao S, Shinde SN, Johnston PJ, Day BW (2009) Design and synthesis of a library of tetracyclic hydroazuleneisoindoles. J Comb Chem 11:486-494.
18. Morton D, Leach S, Cordier C, Warriner S, Nelson A (2009) Synthesis of natural-product- like molecules with over eighty distinct scaffolds. Angew Chem Int Edit 48:104-109.
19. Patel MC, Livinghouse T, Pagenkopf BL (2003) The catalytic intramolecular Pauson-Khand reaction: 2,3,3α,4-tetrahydro-2-(4methylbenzene)sulfonyl] cyclopenta[c]pyrrol-5(1H)-one[(cyclopenta[b]pyrrol-5(1H)-one, 2,3,3α,4-tetrahydro-1-[(4-methylphenyl) sulfonyl]-)]. Org Synth 80:93-103.
20. Hamada T, Suzuki D, Urabe H, Sato F (1999) Titanium alkoxide-based method for stereoselective synthesis of functionalized conjugated dienes. J Am Chem Soc 121:7342-7344.
21. Oh CH, Sung HR, Jung SH, Lim YM(2001) Rhodium-catalyzed [2 + 2 + 2] cyclizations of 1,6-enynes. Tetrahedron Lett 42:5493-5495.
22. 2RuCHR olefin metathesis catalysts: An organometallic success story. Acc Chem Res 34:18-29.
23. Mori M, Sakakibara N, Kinoshita A (1998) Remarkable effect of ethylene gas in the intramolecular enyne metathesis of terminal alkynes. J Org Chem 63:6082-6083.
24. Trost BM, Chen SF (1986) A synthesis of substituted pyrrolidines via a palladium(2+)- catalyzed cyclization. An unusual approach to a carbapenem. J Am Chem Soc 108:6053-6054. (Pubitemid 16023964)
25. Mori M, Saito N, Tanaka D, Takimoto M, Sato Y (2003) Novel alkenylative cyclization using a ruthenium catalyst. J Am Chem Soc 125:5606-5607. (Pubitemid 36592864)
26. Kealy TJ (1962) The chemistry of diazaquinones. 3,6-pyridazinedione and 1,4-phthalazinedione. J Am Chem Soc 84:966-973.
27. Handy ST, Grieco PA, Mineur C, Ghosez L (1995) Lithium trifluoromethanesulfonimide in acetone or diethyl ether as a safe alternative to lithium perchlorate in diethyl ether for effecting Diels-Alder reactions. Unexpected influence of the counterion on exo/ endo selectivity. Synlett 1995:565-567.
28. Li G, Chang H-T, Sharpless KB (1996) Catalytic asymmetric aminohydroxylation (AA) of olefins. Angew Chem Int Edit 35:451-454.
29. Bodkin JA, McLeod MD (2002) The Sharpless asymmetric aminohydroxylation. J Chem Soc Perk T 1 2733-2746.
30. Ganesan A (2008) The impact of natural products upon modern drug discovery. Curr Opin Chem Biol 12:306-317.
31. Cheng T, et al. (2007) Computation of octanol-water partition coefficients by guiding an additive model with knowledge. J Chem Inf Model 47:2140-2148. (Pubitemid 350275080)
32. Sauer WHB, Schwarz MK (2003) Molecular shape diversity of combinatorial libraries: A prerequisite for broad bioactivity. J Chem Inf Comp Sci 43:987-1003.
33. OEChem, version 1.3.4 (OpenEye Scientific Software, Santa Fe, NM), available at www.eyesopen.com.
34. Irwin JJ, Shoichet BK (2005) ZINC-A free database of commercially available compounds for virtual screening. J Chem Inf Model 45:177-182.
35. Vander Heiden MG, Cantley LC, Thompson CB (2009) Understanding the Warburg effect: The metabolic requirements of cell proliferation. Science 324:1029-1033.
36. Ulanovskaya OA, Cui J, Kron SJ, Kozmin SA (2011) A pairwise chemical genetic screen identifies new inhibitors of glucose transport. Chem Biol 18, in press.