Multicomponent reactions – opportunities for the pharmaceutical industry
Tài liệu tham khảo
Paul, 2010, How to improve R&D productivity: the pharmaceutical industry's grand challenge, Nat. Rev. Drug Discov., 9, 203, 10.1038/nrd3078
Dunn, 2012, The importance of green chemistry in process research and development, Chem. Soc. Rev., 41, 1452, 10.1039/C1CS15041C
Ruijter, 2011, Multicomponent reaction design in the quest for molecular diversity & complexity, Angew. Chem. Int. Ed., 50, 6324, 10.1002/anie.201006515
Ganem, 2009, Strategies for innovation in multicomponent reaction design, Acc. Chem. Res., 42, 372, 10.1021/ar800214s
Zhu, 2005
Dömling, 2006, Recent developments in isocyanide based multicomponent reactions in applied chemistry, Chem. Rev., 106, 17, 10.1021/cr0505728
Ugi, 1959, Versuche mit isonitrilen, Angew. Chem., 71, 386
Biginelli, 1891, Ueber aldehyduramide des acetessigäthers, Ber. Dtsch Chem. Ges., 24, 1317, 10.1002/cber.189102401228
Elders, 2009, The efficient one-pot reaction of up to eight components by the union of multicomponent reactions, Angew. Chem. Int. Ed., 48, 5856, 10.1002/anie.200902683
Ramón, 2005, Asymmetric multicomponent reactions (AMCRs): the new Frontier, Angew. Chem. Int. Ed., 40, 1602, 10.1002/anie.200460548
de Graaff, 2012, Recent developments in asymmetric multicomponent reactions, Chem. Soc. Rev., 41, 3969, 10.1039/c2cs15361k
van Berkel, 2012, Recent advances in asymmetric isocyanide-based multicomponent reactions, Eur. J. Org. Chem., 3543, 10.1002/ejoc.201200030
Touré, 2009, Natural product synthesis using multicomponent reaction strategies, Chem. Rev., 109, 4439, 10.1021/cr800296p
Dömling, 2012, Chemistry and biology of multicomponent reactions, Chem. Rev., 112, 3083, 10.1021/cr100233r
Lipinski, 2004, Navigating chemical space for biology and medicine, Nature, 432, 855, 10.1038/nature03193
Koes, 2012, Enabling large-scale design, synthesis and validation of small molecule protein–protein antagonists, PLoS ONE, 7, e32839, 10.1371/journal.pone.0032839
Roughley, 2011, The medicinal chemists’ toolbox: an analysis of reactions used in the pursuit of drug candidates, J. Med. Chem., 54, 3451, 10.1021/jm200187y
Chen, 2012, Identification of diverse modulators of central and peripheral circadian clocks by high-throughput chemical screening, Proc. Natl. Acad. Sci. U.S.A., 109, 101, 10.1073/pnas.1118034108
Gewald, 1966, Heterocyclen aus CH-aciden Nitrilen, VIII. 2-Amino-thiophene aus methylenaktiven Nitrilen, Carbonylverbindungen und Schwefel, Berichte, 99, 94, 10.1002/cber.19660990116
Wyatt, 2008, Identification of an anti-MRSA dihydrofolate reductase inhibitor from a diversity-oriented synthesis, Chem. Commun., 4962, 10.1039/b812901k
Schreiber, 2000, Target-oriented and diversity-oriented organic synthesis in drug discovery, Science, 287, 1964, 10.1126/science.287.5460.1964
O’Connor, C.J., et al. Diversity-oriented synthesis: producing chemical tools for dissecting biology. Chem. Soc. Rev. (in press)
Dückert, 2012, Natural product – inspired cascade synthesis yields modulators of centrosome integrity, Nat. Chem. Biol., 8, 179, 10.1038/nchembio.758
Wetzel, 2011, Biology-oriented synthesis, Angew. Chem. Int. Ed., 50, 10800, 10.1002/anie.201007004
Pando, 2011, The multiple multicomponent approach to natural product mimics: tubugis, N-substituted anticancer peptides with picomolar activity, J. Am. Chem. Soc., 133, 7692, 10.1021/ja2022027
Henkel, 2003, Convergent multicomponent assembly of 2-acyloxymethyl thiazoles, Tetrahedron Lett., 44, 8947, 10.1016/j.tetlet.2003.10.012
Dömling, 2007, Total synthesis of tubulysin U and V, Angew. Chem. Int. Ed., 46, 2347, 10.1002/anie.200790053
Tanino, 2010, Total synthesis of (−)-muraymycin D2 and its epimer, J. Org. Chem., 75, 1366, 10.1021/jo9027193
Tanino, 2010, Synthesis and biological evaluation of muraymycin analogues active against anti-drug-resistant bacteria, ACS Med. Chem. Lett., 1, 258, 10.1021/ml100057z
Sheldon, 2007, The E factor: fifteen years on, Green Chem., 9, 1273, 10.1039/b713736m
Anastas, 1998
Trost, 1991, The atom economy – a search for synthetic efficiency, Science, 254, 1471, 10.1126/science.1962206
Wender, 2008, Function oriented synthesis, step economy, and drug design, Acc. Chem. Res., 41, 40, 10.1021/ar700155p
Isocyanides are stable organic compounds. Their toxicity is, with some exceptions, actually quite low compared to many standard chemicals
Ugi, I., Steinbrückner, C. (1959). A.B. Astra. DE-B 1103337
Bossert, 1981, 4-Aryldihydropyridines, a new class of highly active calcium antagonists, Angew. Chem. Int. Ed., 20, 762, 10.1002/anie.198107621
Rossen, 1998, An efficient asymmetric hydrogenation approach to the synthesis of the Crixivan® piperazine intermediate, Tetrahedron Lett., 39, 6823, 10.1016/S0040-4039(98)01484-1
Kalinski, 2008, Multicomponent reactions as powerful tool for generic drug synthesis, Synthesis, 4007, 10.1055/s-0028-1083239
Dömling, 2010, Praziquantel and schistosomiasis, ChemMedChem, 5, 1420, 10.1002/cmdc.201000202
Znabet, 2010, A highly efficient synthesis of telaprevir by strategic use of biocatalysis and multicomponent reactions, Chem. Commun., 46, 7918, 10.1039/c0cc02823a
Znabet, 2010, Highly stereoselective synthesis of substituted prolyl peptides by combination of biocatalytic desymmetrization and multicomponent reactions, Angew. Chem. Int. Ed., 49, 5289, 10.1002/anie.201001592
