Abstract:
Fluorination reactions of medicinal and biologically-active compounds will be discussed. Late stage fluorination strategies of medicinal targets have recently attracted considerable attention on account of the influence that a fluorine atom can impart to targets of medicinal importance, such as modulation of lipophilicity, electronegativity, basicity and bioavailability, the latter as a consequence of membrane permeability. Therefore, the recourse to late-stage fluorine substitution on compounds with already known and relevant biological activity can provide the pharmaceutical industry with new leads with improved medicinal properties. The fluorination strategies will take into account different fluorinating reagents, either of nucleophilic or electrophilic, and of radical nature. Diverse families of organic compounds such as (hetero)aromatic rings, and aliphatic substrates (sp3, sp2, and sp carbon atoms) will be studied in late-stage fluorination reaction strategies. © 2014 The Royal Society of Chemistry.
Registro:
Documento: |
Artículo
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Título: | Fluorination methods in drug discovery |
Autor: | Yerien, D.E.; Bonesi, S.; Postigo, A. |
Filiación: | Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires-CONICET, Junín 954, Buenos Aires, CP 1113, Argentina Departamento de Química Orgánica, CIHIDECAR-CONICET, Pabellón II, Ciudad Universitaria, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, 1428, Argentina
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Palabras clave: | Bioactivity; Biochemistry; Carbon; Chemical bonds; Electronegativity; Fluorination; Halogenation; Aromatic rings; Biologically active compounds; Drug discovery; Fluorination reactions; Fluorine atoms; Fluorine substitution; Membrane permeability; Pharmaceutical industry; Fluorine; fluorinated hydrocarbon; fluorine; chemical structure; chemistry; drug development; halogenation; synthesis; Drug Discovery; Fluorine; Halogenation; Hydrocarbons, Fluorinated; Molecular Structure |
Año: | 2016
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Volumen: | 14
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Número: | 36
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Página de inicio: | 8398
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Página de fin: | 8427
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DOI: |
http://dx.doi.org/10.1039/c6ob00764c |
Título revista: | Organic and Biomolecular Chemistry
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Título revista abreviado: | Org. Biomol. Chem.
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ISSN: | 14770520
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CODEN: | OBCRA
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CAS: | fluorine, 7782-41-4; Fluorine; Hydrocarbons, Fluorinated
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v14_n36_p8398_Yerien |
Referencias:
- Zhou, Y., Wang, J., Gu, Z., Wang, S., Zhu, W., Aceña, J.L., Soloshonok, V.A., Liu, H., (2016) Chem. Rev., 116, pp. 422-528
- Harsanyi, A., Sandford, G., (2015) Green Chem., 17, pp. 2081-2086
- Wang, J., Sanchez-Roselló, M., Aceña, J.L., Del Pozo, C., Sorochinsky, A.E., Fustero, S., Soloshonok, V.A., Liu, H., (2014) Chem. Rev., 114 (4), pp. 2432-2506
- Gillis, E.P., Eastman, K.J., Hill, M.D., Donnelly, D.J., Meanwell, N.A., (2015) J. Med. Chem., 58, pp. 8315-8359
- Filler, R., Saha, R., (2009) Future Med. Chem., 1 (5), pp. 777-791
- Hagmann, W., (2008) J. Med. Chem., 51 (15), pp. 4359-4369
- Müller, K., Faeh, C., Diederich, F., (2007) Science, 317, pp. 1881-1886
- Bégué, J.-P., Bonnet-Delpon, D., (2006) J. Fluorine Chem., 127, pp. 992-1012
- Kirk, K.L., (2006) J. Fluorine Chem., 127, pp. 1013-1029
- Böhm, H.J., Banner, D., Bendels, S., Kansy, M., Kuhn, B., Müller, K., Obst-Sander, U., Stahl, M., (2004) ChemBioChem, 5, pp. 637-643
- Kirk, K.L., (2006) Curr. Top. Med. Chem., 6, pp. 1445-1543
- Gouverneur, V., Konrad, S., (2015) Chem. Rev., 115 (2), pp. 563-565
- O'Hagan, D., (2010) J. Fluorine Chem., 131, pp. 1071-1081
- Kirk, K.L., (2008) Org. Process Res. Dev., 12, pp. 305-321
- Purser, S., Moore, P.R., Swallow, S., Gouverneur, V., (2008) Chem. Soc. Rev., 37, pp. 320-330
- Gouverneur, V., (2012) Fluorine in Pharmaceuticals and Medicinal Chemistry: From Biophysical Aspects to Clinical Applications". Volume 6, Molecular Medicine and Medicinal Chemistry, , ed., Imperial College Press
- Ojima, I., (2009) Fluorine in Medicinal Chemistry and Chemical Biology, , ed., Blackwell Publishing, Ltd., John Wiley & Sons Publications
- Begué, J.-P., Bonnet-Delpon, D., (2008) Bioorganic and Medicinal Chemistry of Fluorine, , BioCIS-CNRS, Wiley
- Huchet, Q.A., Kuhn, B., Wagner, B., Kratochwil, N.A., Fischer, H., Kansy, M., Zimmerli, D., Müller, K., (2015) J. Med. Chem., 58 (22), pp. 9041-9060
- Morgenthaler, M., Scheweizer, E., Hoffmann-Roder, A., Benini, F., Martin, R.E., Jaeschke, G., Wagner, B., Muller, K., (2007) ChemMedChem, 2, p. 1100
- Dawadi, S., Viswanathan, K., Boshoff, H.I., Barry, C.E., III, Aldrich, C.C., (2015) J. Org. Chem., 80, pp. 4835-4850
- Engelhart, C.A., Drake, E.J., Wilson, D.J., Fu, P., Boshoff, H.I., Barry, C.E., III, Gulick, A.M., Aldrich, C.C., (2013) J. Med. Chem., 56, p. 2385
- Ojima, I., (2009) Section 1. Fluorine-containing Drugs for Human Use Approved by FDA in the United States. Fluorine in Medicnal Chemistry and Cheical Biology, , ed., Blackwell Publishing Ltd., ISBN 978-1-405-16720-8
- http://www.fda.gov/downloads/Drugs/DevelopmentApprovalProcess/DrugInnovation/UCM381803.pdf, New FDA approved drugs in 2013; Shimizu, M., Hiyama, T., (2005) Angew. Chem., Int. Ed., 44, pp. 214-231
- Hollingworth, C., Gouverneur, V., ; RSC Catalysis Series, 2013, 11(C-H and C-X Bond Functionalization), 193-261; Tredwell, M., Gouverneur, V., (2012) Compr. Chirality, 1, pp. 70-85
- Singh, R.P., Shreeve, J.-M., (2004) Acc. Chem. Res., 37, pp. 31-44
- Preshlock, S., Tredwell, M., Gouverneur, V., (2016) Chem. Rev., 116, pp. 719-766
- Buckingham, F., Gouverneur, V., (2016) Chem. Sci., 7, pp. 1645-1652
- Verhoog, S., Pfeifer, L., Khotavivattana, T., Calderwood, S., Collier, T.L., Wheelhouse, K., Tredwell, M., Gouverneur, V., (2016) Synlett, pp. 25-28
- Buckingham, F., Kirjavainen, A.N., Forsback, S., Krzyczmonik, A., Keller, T., Newington, I.M., Glaser, M., Gouverneur, V., (2015) Angew. Chem., Int. Ed., 54 (45), pp. 13366-13369
- Khotavivattana, T., Verhoog, S., Tredwell, M., Pfeifer, L., Calderwood, S., Wheelhouse, K., Collier, T.L., Gouverneur, V., (2015) Angew. Chem., Int. Ed., 54 (34), pp. 9991-9995
- Tredwell, M., Preshlock, S.M., Taylor, N.J., Gruber, S., Huiban, M., Passchier, J., Mercier, J., Gouverneur, V., (2014) Angew. Chem., Int. Ed., 53 (30), pp. 7751-7755
- Brooks, A.F., Drake, L.R., Stewart, M.N., Cary, B.P., Jackson, I.M., Mallette, D., Mossine, A.V., Scott, P.J.H., (2016) Pharm. Pat. Anal., 5, pp. 17-47
- Chansaenpak, K., Vabre, B., Gabbaï, F.P., (2016) Chem. Soc. Rev., 45, pp. 954-971
- Meyer, P., Westwell, A.D., (2015) Synthesis of Fluorinated Pharmaceuticals, pp. 6-17. , (10.4155/fseb2013.14.295)
- Rehm, T.H., (2016) Chem. Eng. Technol., 39, pp. 66-80
- Samori, C., Guerrini, A., Varchi, G., Fontana, G., Bombardelli, E., Tinelli, S., Beretta, G.L., Battaglia, A., (2009) J. Med. Chem., 52, p. 1029
- Kopyra, J., Kellerb, A., Bald, I., (2014) RSC Adv., 4, p. 6825
- Middleton, W.J., (1975) J. Org. Chem., 40, p. 574
- Hayashi, H., Sonoda, H., Fukumura, K., Nagata, T., (2002) Chem. Commun., p. 1618
- Lal, G.S., Pez, G.P., Pesaresi, R.J., Prozonic, F.M., Cheng, H., (1999) J. Org. Chem., 64, p. 7048
- Kremsner, J.M., Rack, M., Pilger, C., Kappe, C.O., (2009) Tetrahedron Lett., 50, pp. 3665-3668
- Schimler, S.D., Ryan, S.J., Bland, D.C., Anderson, J.E., Sanford, M.S., (2015) J. Org. Chem., 80, pp. 12137-12145
- Taylor, S.D., Kotoris, C.C., Hum, G., (1999) Tetrahedron, 55, pp. 12431-12477
- Banks, R.E., Mohialdin-Khaffaf, S.N., Lal, G.S., Sharif, I., Syvret, R.G., (1992) J. Chem. Soc., Chem. Commun., 8, pp. 595-596
- Banks, R.E., Besheesh, M.K., Mohialdin-Khaffaf, S.N., Sharif, I., (1996) J. Chem. Soc., Perkin Trans. 1, pp. 2069-2076
- Banks, R.E., (1998) J. Fluorine Chem., 87, pp. 1-17
- Sankar Lal, G., Pez, G.P., Syvre, R.G., (1996) Chem. Rev., 96 (5), pp. 1737-1756
- Umemoto, T., Kawada, K., Tomita, K., (1986) Tetrahedron Lett., 27, pp. 4465-4468
- Umemoto, T., Fukami, S., Tomizawa, G., Harasawa, K., Kawada, K., Tomia, K., (1990) J. Am. Chem. Soc., 112, pp. 8563-8575
- Umemoto, T., Tomizawa, G., (1995) J. Org. Chem., 60, pp. 6563-6570
- Shibata, N., Tarui, T., Doi, Y., Kirk, K.L., (2001) Angew. Chem., Int. Ed., 40, pp. 4461-4463. , Angew. Chem. 2001 113 4593
- Tréguier, B., Roche, S.P., (2014) Org. Lett., 16, pp. 278-281
- Differding, E., Ofner, H., (1991) Synlett, pp. 187-189
- Fukushi, K., Suzuki, S., Kamo, T., Tokunaga, E., Sumii, Y., Kagawa, T., Kawada, K., Shibata, N., (2016) Green Chem., 18, pp. 1864-1868
- Stavber, S., Pecn, T.S., Papez, M., Zupan, M., (1996) Chem. Commun., pp. 2247-2248
- Geary, G.C., Hope, E.G., Singh, K., Stuart, A.M., (2015) RSC Adv., 5, p. 16501
- Geary, G.C., Hope, E.G., Singh, K., Stuart, A.M., (2013) Chem. Commun., 49 (81), pp. 9263-9265
- Tang, P., Wang, W., Ritter, T., (2011) J. Am. Chem. Soc., 133, pp. 11482-11484
- Sladojevich, F., Arlow, S.I., Tang, P., Ritter, T., (2013) J. Am. Chem. Soc., 135, p. 2470
- Fujimoto, T., Becker, F., Ritter, T., (2014) Org. Process Res. Dev., 18, p. 1041
- Campbell, M.G., Ritter, T., (2014) Org. Process Res. Dev., 18, pp. 474-480
- Nielsen, M.K., Ugaz, C.R., Li, W., Doyle, A.G., (2015) J. Am. Chem. Soc., 137 (30), pp. 9571-9574
- Wenz, J., Rettenmeier, C.A., Wadepohl, H., Gade, L.H., (2016) Chem. Commun., 52, pp. 202-205
- L'Heureux, A., Beaulieu, F., Bennett, C., Bill, D.R., Clayton, S., LaFlamme, F., Mirmehrabi, M., Couturier, M., (2010) J. Org. Chem., 75 (10), pp. 3401-3411
- Zeng, Y., Hu, J., (2015) Rep. Org. Chem., 5, pp. 19-39
- Cernak, T., Dykstra, K.D., Tyagarajan, S., Vachal, P., Krska, S.W., (2016) Chem. Soc. Rev., 45, pp. 546-576
- Champagne, P.A., Desroches, J., Hamel, J.-D., Vandamme, M., Paquin, J.-F., (2015) Chem. Rev., 115 (17), pp. 9073-9174
- Neumann, C.N., Ritter, T., (2015) Angew. Chem., Int. Ed., 54, pp. 2-8
- Lou, S.-J., Chen, Q., Wang, Y.-F., Xu, D.-Q., Du, X.-H., He, J.-Q., Mao, Y.-J., Xu, Z.-Y., (2015) ACS Catal., 5 (5), pp. 2846-2849
- Bach, P., Boström, J., Brickmann, K., Burgess, L.E., Clarke, D., Groneberg, R.D., Harvey, D.M., Laird, E.R., (2013) Future Med. Chem., 5, pp. 2037-2056
- Hull, K.L., Anani, W.Q., Sanford, M.S., (2006) J. Am. Chem. Soc., 128, pp. 7134-7135
- Liu, B., Jiang, H.-Z., Shi, B.-F., (2014) J. Org. Chem., 79, pp. 1521-1526
- Ma, W., Ackermann, L., (2013) Chem.-Eur. J., 19, pp. 13925-13928
- Yao, J., Feng, R., Wu, Z., Liu, Z., Zhang, Y., (2013) Adv. Synth. Catal., 355, pp. 1517-1522
- Niu, L., Yang, H., Wang, R., Fu, H., (2012) Org. Lett., 14, pp. 2618-2621
- Ackermann, L., Diers, E., Manvar, A., (2012) Org. Lett., 14, pp. 1154-1157
- Chu, J.-H., Lin, P.-S., Wu, M.-J., (2010) Organometallics, 29, pp. 4058-4065
- Jia, X., Zhang, S., Wang, W., Luo, F., Cheng, J., (2009) Org. Lett., 11, pp. 3120-3123
- Kakiuchi, F., Igi, K., Matsumoto, M., Hayamizu, T., Chatani, N., Murai, S., (2002) Chem. Lett., 3, pp. 396-397
- Campbell, M.G., Ritter, T., (2015) Chem. Rev., 115, pp. 612-633
- Yang, X., Wu, T., Phipps, R.J., Toste, F.D., (2015) Chem. Rev., 115, pp. 826-870
- Hollingworth, C., Gouverneur, V., (2012) Chem. Commun., 48, pp. 2929-2942
- Furuya, T., Kamlet, A.S., Ritter, T., (2011) Nature, 473, pp. 470-477
- Grushin, V.V., (2010) Acc. Chem. Res., 43, pp. 160-171
- Watson, D.A., Su, M.J., Teverovskiy, G., Garcia-Fortanet, Y., Kinzel, T., Buchwald, S.L., (2009) Science, 325, p. 1661
- Ye, Y.D., Sanford, M.S., (2013) J. Am. Chem. Soc., 135 (12), pp. 4648-4651
- Furuya, T., Strom, A.E., Ritter, T., (2009) J. Am. Chem. Soc., 131, p. 1662
- Tang, P.P., Furuya, T., Ritter, T., (2010) J. Am. Chem. Soc., 132, p. 12150
- Furuya, T., Kaiser, H.M., Ritter, T., (2008) Angew. Chem., Int. Ed., 47, p. 5993
- Furuya, T., Ritter, T., (2009) Org. Lett., 11, p. 2860
- Tang, P.P., Ritter, T., (2011) Tetrahedron, 67, p. 4449
- Eunsung, L., Kamlet, A.S., Powers, D.C., Neumann, C.N., Boursalian, G.B., Furuya, T., Choi, D.C., Ritter, T., (2011) Science, 334, pp. 639-642
- Fier, P.S., Hartwig, J.F., (2012) J. Am. Chem. Soc., 134 (26), pp. 10795-10798
- Fier, P.S., Luo, J.W., Hartwig, J.F., (2013) J. Am. Chem. Soc., 135 (7), pp. 2552-2559
- Sather, A.C., Lee, H.G., De La Rosa, V.Y., Yang, Y., Müller, P., Buchwald, S.L., (2015) J. Am. Chem. Soc., 137 (41), pp. 13433-13438
- Huang, S.M., (2009) Nature, 461, p. 614
- Yamada, S., Gavryushin, A., Knochel, P., (2010) Angew. Chem., Int. Ed., 49 (12), pp. 2215-2218
- Clark, J.H., Wails, D., Bastock, T.W., (1996) Aromatic Fluorination, , CRC Press, Boca Raton, FL
- Kuduk, S.D., DiPardo, R.M., Bock, M.G., (2005) Org. Lett., 7, p. 577
- Sydonie, D., Schimler, D., Ryan, S.J., Bland, D.C., Anderson, J.E., Sanford, M.S., (2015) J. Org. Chem., 80 (24), pp. 12137-12145
- Furuya, T., Klein, J.E.M.N., Ritter, T., (2010) Synthesis, p. 1804
- Miller, J., (1968) Aromatic Nucleophilic Substitution, , Elsevier, London
- Terrier, F., (2013) Modern Nucleophilic Aromatic Substitution, , Wiley-VCH, Weinheim, Germany
- Smith, D.A., Jones, R.M., (2008) Curr. Opin. Drug Discovery Dev., 11, pp. 72-79
- Buckingham, F., Calderwood, S., Checa, B., Keller, T., Tredwell, M., Lee Collier, T., Newington, I.M., Gouverneur, V., (2015) J. Fluorine Chem., 180, pp. 33-39
- Fier, P.S., Hartwig, J.F., (2013) Science, 342, pp. 956-960
- Izawa, K., Acena, J.L., Wang, J., Soloshonok, V.A., Liu, H., (2016) Eur. J. Org. Chem., pp. 8-16
- Leahy, D.K., (2012) Org. Process Res. Dev., 16, pp. 244-249
- Serdyuk, O.V., Muzalevskiy, V.M., Nenajdenko, V.G., (2012) Synthesis, pp. 2115-2137
- Albertshofer, K., Mani, N.S., (2016) J. Org. Chem., 81 (3), pp. 1269-1276
- Jiang, Z., Ni, T., Wei, C., Tian, S., Li, Y., Dai, L., Liu, H., Zhang, D., (2013) Synlett, pp. 0215-0218
- Liu, P., Gao, Y., Gu, W., Shen, Z., Sun, P., (2015) J. Org. Chem., 80 (22), pp. 11559-11565
- Greenblatt, D.J., Roth, T., (2012) Expert Opin. Pharmacother., 13, p. 879
- Langer, S.Z., Arbilla, S., Benavides, J., Scatton, B., (1990) Adv. Biochem. Psychopharmacol., 46, p. 61
- Yamane, I., Hagino, H., Okano, T., Enokida, M., Yamasaki, D., Teshima, R., (2003) Arthritis Rheum., 48, p. 1732
- Mizushige, K., Ueda, T., Yukiiri, K., Suzuki, H., (2002) Cardiovasc. Drug Rev., 20, p. 163
- Katsura, Y., Nishino, S., Takasugi, H., (1991) Chem. Pharm. Bull., 39, p. 2937
- Nyffeler, P.T., Durón, S.G., Burkart, M.D., Vincent, S.P., Wong, C.H., (2005) Angew. Chem., Int. Ed., 44, p. 192
- Lin, R.-Y., Ding, S.-T., Shi, Z.-Z., Jiao, N., (2011) Org. Lett., 13, p. 4498
- Arcadi, A., Pietropaolo, E., Alvino, A., Michelet, V., (2013) Org. Lett., 15, p. 2766
- Yang, L., Ma, Y.-H., Song, F.-J., You, J.-S., (2014) Chem. Commun., 50, p. 3024
- Wang, M.-L., Liu, X.-X., Zhou, L., Zhu, J.-D., Sun, X., (2015) Org. Biomol. Chem., 13, p. 3190
- Breen, J.R., Sandford, G., Patel, B., Fray, J., (2015) Synlett, p. 51
- O'Leary, E.M., Jones, D.J., O'Donovan, F.P., O'Sullivan, T.P., (2015) J. Fluorine Chem., 176, pp. 93-120
- Zhang, H., Wang, B., Cui, L., Bao, X., Qu, J., Song, Y., (2015) Eur. J. Org. Chem., pp. 2143-2147
- Lam, Y.-H., Houk, K.N., (2014) J. Am. Chem. Soc., 136 (27), pp. 9556-9559
- Zhao, J.-F., Duan, X.-H., Yang, H., Guo, L.-N., (2015) J. Org. Chem., 80 (21), pp. 11149-11155
- Nguyen, N., Fakra, E., Pradel, V., Jouve, E., Alquier, C., Le Guern, M.E., Micallef, J., Blin, O., (2006) Hum. Psychopharmacol., 21 (3), pp. 139-149
- Wolstenhulme, J.R., Gouverneur, V., (2014) Acc. Chem. Res., 47 (12), pp. 3560-3570
- Hicken, E.J., Marmsater, F.P., Munson, M.C., Schlachter, S.T., Robinson, J.E., Allen, S., Burgess, L.E., Lyssikatos, J.P., (2014) ACS Med. Chem. Lett., 5, p. 78
- Duncan, K.W., Chesworth, R., Boriack-Sjodin, P.A., Munchhof, M.J., Jin, L., Prmt5 inhibitors containing a dihydro- or tetrahydroisoquinoline and uses thereof (2014) Patent WO, pp. 2014100730A1
- Vasdev, N., Cao, P., Van Oosten, E.M., Wilson, A.A., Houle, S., Hao, G., Sun, X., Kulkarni, P., (2012) MedChemComm, 3, p. 1228
- Keri, R.S., Patil, S.A., Budagumpi, S., Srinivasa, B.M., (2015) Chem. Biol. Drug Des., 86 (4), pp. 410-423
- Wang, D., Sun, W., Chu, T., (2015) Eur. J. Org. Chem., pp. 4114-4118
- Isanbor, C., O'Hagan, D., (2006) J. Fluorine Chem., 127, pp. 303-319
- Codington, J.F., Doerr, I., Praag, D.V., Bendich, A., Fox, J.J., (1961) J. Am. Chem. Soc., 83, p. 5030
- Thibaudeau, C., Plavec, J., Chattopadhyaya, J., (1998) J. Org. Chem., 63, p. 4967
- Barchi, J.J., Jr., Jeong, L.-S., Siddiqui, S.A., Marquez, V.E., (1997) J. Biochem. Biophys. Methods, 34, p. 11
- Lee, K., Choi, Y., Gumina, G., Zhou, W., Schinazi, R.F., Chu, C.K., (2002) J. Med. Chem., 45, p. 1313
- Chong, Y., Gumina, G., Mathew, J.S., Schinazi, R.F., Chu, C.K., (2003) J. Med. Chem., 46, p. 3245
- Zhou, W., Gumina, G., Chong, Y., Wang, J., Schinazi, R.F., Chu, C.K., (2004) J. Med. Chem., 47, p. 3399
- Biffinger, J.C., Kim, H.W., DiMagno, S.G., (2004) ChemBioChem, 5, p. 622
- Hu, X.-G., Hunter, L., (2013) Beilstein J. Org. Chem., 9, pp. 2696-2708
- Shaw, S.J., Golf, D.A., Boralsky, L.A., Irving, M., Singh, R., (2013) J. Org. Chem., 78, pp. 8892-8897
- Rowley, M., Hallett, D.J., Goodacre, S., Moyes, C., Crawforth, J., Sparey, T.J., Patel, S., MacLeod, A.M., (2001) J. Med. Chem., 44, pp. 1603-1614
- Nash, R.J., Kato, A., Yu, C.-Y., Fleet, G.W., (2011) Future Med. Chem., 3, pp. 1513-1521
- Prell, E., Korb, C., Kluge, R., Ströhl, D., Csuk, R., (2010) Arch. Pharm., 343, pp. 583-589
- Sankar Lal, G., (1995) Synth. Commun., 25 (5), pp. 725-737
- Wójtowicz-Rajche, H., (2012) J. Fluorine Chem., 143, pp. 11-48
- Brown, K., Dixey, M., Weymouth-Wilson, A., Linclau, B., (2014) Carbohydr. Res., 387, pp. 59-73
- Chen, P., Liu, G., (2015) Eur. J. Org. Chem., pp. 4295-4309
- Peifer, M., Berger, R., Shurtleff, V.W., Conrad, J.C., MacMillan, D.W.C., (2014) J. Am. Chem. Soc., 136, pp. 5900-5903
- Kwiatkowski, P., Beeson, T.D., Conrad, J.C., MacMillan, D.W., (2011) J. Am. Chem. Soc., 133, pp. 1738-1741
- Martin, J.A., Bushnell, D.J., Duncan, I.B., Dunsdon, S.J., Hall, M.J., MacHin, P.J., Merrett, J.H., Kinchington, D.J., (1990) J. Med. Chem., 33, pp. 2137-2145
- Balzarini, J., Baba, M., Pauwels, R., Herdewijn, P., De Clercq, E., (1988) Biochem. Pharmacol., 37, pp. 2847-2856
- Bonate, P.L., Arthaud, L., Stephenson, K., Secrist, J.A., Weitman, S., (2006) Nat. Rev. Drug Discovery, 5, pp. 855-863
- Faderl, S., Gandhi, V., Keating, M.J., Jeha, S., Plunket, W., Kantarjian, H.M., (2005) Cancer, 103, pp. 1985-1995
- Martínez-Monteroa, S., Fernándeza, S., Sanghvic, Y.S., Theodorakisb, E.A., Detoriod, M.A., McBrayere, T.R., Whitakere, T., Ferrero, M., (2012) Bioorg. Med. Chem., 20 (23), pp. 6885-6893
- Ghosh, A.K., Lagisetty, P., Zajc, B., (2007) J. Org. Chem., 72, pp. 8222-8226
- Bertolini, G., Deleo, M., Frigerio, M., Losa, M., Velati, M., Process and intermediates for preparing emtricitabine (2011) US Pat., p. 7939660B2
- Koperniku, A., Liu, H., Hurley, P.B., (2016) Eur. J. Org. Chem., pp. 871-886
- Thompson, W.J., Anderson, P.S., Britcher, S.F., Lyle, T.A., Thies, J.E., Magill, C.A., Varga, S.L., Christy, M.E., (1990) J. Med. Chem., 33, p. 789
- Andres, J.I., Alonso, J.M., Diaz, A., Fernandez, J., Iturrino, L., Martinez, P., Matesanz, E., De Chaffoy, D., (2002) Bioorg. Med. Chem. Lett., 12, p. 653
- Nodwell, M.B., Bagai, A., Halperin, S.D., Martin, R.E., Knust, H., Britton, R., (2015) Chem. Commun., 51 (59), pp. 11783-11786
- Liu, W., Groves, J.T., (2013) Angew. Chem., Int. Ed., 52, pp. 1-5
- Liu, W., Huang, X., Groves, J.T., (2013) Nat. Protoc., 8, pp. 2348-2354
- Liu, W., Huang, X., Cheng, M.J., Nielsen, R.J., Goddard, W.A., III, Groves, J.T., (2012) Science, 337, pp. 1322-1325
- Zhu, Q., Ji, D., Liang, T., Wang, X., Xu, Y., (2015) Org. Lett., 17, pp. 3798-3801
- Godard J-I, ; (1994) From Fluorine Med. 21st Century, Conf. Pap., , Strategies for introducing fluorine into corticosteroids Paper 10, 16
- O'Hagan, D., (2010) J. Fluorine Chem., 131, pp. 1071-1081
- Lee, H.J., Taraporewala, I.B., Heiman, A.S., (1989) Drugs Today, 25, pp. 577-588
- Li, J., Goto, M., Yang, X., Morris-Natschke, S.L., Huang, L., Chen, C.-H., Lee, K.-H., (2016) Bioorg. Med. Chem. Lett., 26, pp. 68-71
- Ishida, N., Kawabata, N.O., Shimazaki, A., Hara, H., (2006) Cardiovasc. Drug Rev., 24, pp. 1-10
- Markovskii, L.N., Pashinnik, V.E., Kirsanov, A.V., (1973) Synthesis, p. 787
- Matsumura, Y., Mori, N., Nakano, T., Sasakura, H., Matsugi, T., Harab, H., Morizawa, Y., (2004) Tetrahedron Lett., 45, pp. 1527-1529
- Zhang, X., Guo, S., Tang, P., (2015) Org. Chem. Front., 2, pp. 806-810
- House, D.A., (1962) Chem. Rev., 62, p. 185
- Nyffeler, P.T., Durón, S.G., Burkhart, M.D., Vincent, S.P., Wong, C.H., (2004) Angew. Chem., 117, p. 196. , Angew. Chem., Int. Ed. 2004 44 192
- Rueda-Becerril, M., Sazepin, C.C., Leung, J.C.T., Okbinoglu, T., Kennepohl, P., Paquin, J., Sammis, G.M., (2012) J. Am. Chem. Soc., 134, p. 4026
- Yin, F., Wang, Z., Li, Z., Li, C., (2012) J. Am. Chem. Soc., 134, p. 10401
- Barker, T.J., Boger, D.L., (2012) J. Am. Chem. Soc., 134, p. 13588
- Zhang, C., Li, Z., Zhu, L., Yu, L., Wang, Z., Li, C., (2013) J. Am. Chem. Soc., 135, p. 14082
- Rueda-Becerril, M., Mahé, O., Drouin, M., Majewski, M.B., West, J.G., Wolf, M.O., Sammis, G.M., Paquin, J., (2014) J. Am. Chem. Soc., 136, p. 2637
- Halperin, S.D., Kwon, D., Holmes, M., Regalado, E.L., Campeau, L.-C., DiRocco, D.A., Britton, R., (2015) Org. Lett., 17, pp. 5200-5203
- Baumann, M., Baxendale, I.R., Ley, S.V., (2011) Mol. Diversity, 15, pp. 613-630
- Stavber, G., Zupan, M., Stavber, S., (2009) Synlett, p. 589
- Ahlsten, N., Martin-Matute, B., (2011) Chem. Commun., 47, p. 8331
- Yang, Q., Mao, L., Yang, B., Yang, S., (2014) Org. Lett., 16, p. 3460
- Wang, W., Jasinski, W.J., Hammond, G.B., Xu, B., (2010) Angew. Chem., Int. Ed., 49, p. 7247
- Rajawinslin, R.R., Raihan, M.J., Janreddy, D., Kavala, V., Kuo, C., Kuo, T., Chen, M., Yao, C., (2013) Eur. J. Org. Chem., p. 5743
- Zhang, M., Gong, Y., Wang, W., (2013) Eur. J. Org. Chem., p. 7372
- Yang, H., Xu, B., Hammond, G.B., (2008) Org. Lett., 10, p. 5589
- Shibata, N., Ishimaru, T., Nakamura, S., Toru, T., (2007) J. Fluorine Chem., 128, pp. 469-483
- Ishimaru, T., Shibata, N., Horikawa, T., Yasuda, N., Nakamura, S., Toru, T., Shiro, M., (2008) Angew. Chem., Int. Ed., 120, pp. 4225-4229
- Shibata, N., Suzuki, E., Asahi, T., Shiro, M., (2001) J. Am. Chem. Soc., 123 (29), pp. 7001-7009
- Saadi, J., Wennemers, H., (2016) Nat. Chem., 8, pp. 276-280
- Dias, L.C., Vieiraand Eliezer, A.S., Barreiro, J., (2016) Org. Biomol. Chem., 14, pp. 2291-2296
- Willis, N.J., Fisher, C.A., Alder, C.M., Harsanyi, A., Shukla, L., Adams, J.P., Sandford, G., (2016) Green Chem., 18, pp. 1313-1318
- Curtis, N.R., Davies, S., Gray, M., Leach, S.G., McKie, R.A., Vernon, L.E., Walkington, A., (2015) Org. Process Res. Dev., 19, pp. 865-871
- Van Pelt, S., Teeuwen, R.L.M., Janssen, M.H.A., Sheldon, R.A., Dunn, P.J., Howard, R.M., Kumar, R., Wong, J.W., (2011) Green Chem., 13, pp. 1791-1798
- Surmont, R., Verniest, G., De Kimpe, N., (2010) Org. Lett., 12, pp. 4648-4651
- Fustero, S., Sanz-Cervera, J.F., Aceña, J.L., Sánchez-Roselló, M., (2009) Synlett, pp. 525-549
- Britton, R.G., Horner-Glister, E., Pomenya, O.A., Smith, E.E., Denton, R., Jenkins, P.R., Steward, W.P., Sale, S., (2012) Eur. J. Med. Chem., 54, pp. 952-958
- Dong, X., Yang, W., Hu, W., Sun, J., (2015) Angew. Chem., Int. Ed., 54, pp. 660-663
- Cooper, J.B., (2002) Curr. Drug Targets, 3, p. 155
- Hu, X.-G., Lawer, A., Peterson, M.B., Iranmanesh, H., Ball, G.E., Hunter, L., (2016) Org. Lett., 18 (4), pp. 662-665
- Chen, G., Song, J., Yu, Y., Luo, X., Li, C., Huang, X., (2016) Chem. Sci., 7, pp. 1786-1790
- Kong, W., Merino, E., Nevado, C., (2014) Chimia, 68 (6), pp. 430-435
- Wu, L., Chen, P., Liu, G., (2016) Org. Lett., 18 (5), pp. 960-963
- Ulmer, A., Brunner, C., Arnold, A.M., Pçthig, A., Gulder, T., (2016) Chem.-Eur. J., 22, pp. 3660-3664
- Xu, T., Liu, G., (2012) Org. Lett., 14, pp. 5416-6519
Citas:
---------- APA ----------
Yerien, D.E., Bonesi, S. & Postigo, A.
(2016)
. Fluorination methods in drug discovery. Organic and Biomolecular Chemistry, 14(36), 8398-8427.
http://dx.doi.org/10.1039/c6ob00764c---------- CHICAGO ----------
Yerien, D.E., Bonesi, S., Postigo, A.
"Fluorination methods in drug discovery"
. Organic and Biomolecular Chemistry 14, no. 36
(2016) : 8398-8427.
http://dx.doi.org/10.1039/c6ob00764c---------- MLA ----------
Yerien, D.E., Bonesi, S., Postigo, A.
"Fluorination methods in drug discovery"
. Organic and Biomolecular Chemistry, vol. 14, no. 36, 2016, pp. 8398-8427.
http://dx.doi.org/10.1039/c6ob00764c---------- VANCOUVER ----------
Yerien, D.E., Bonesi, S., Postigo, A. Fluorination methods in drug discovery. Org. Biomol. Chem. 2016;14(36):8398-8427.
http://dx.doi.org/10.1039/c6ob00764c