Fluorination methods in drug discovery

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 modu...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autor principal: Yerien, D.E
Otros Autores: Bonesi, S., Postigo, A.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: Royal Society of Chemistry 2016
Materias:
Acceso en línea:Registro en Scopus
DOI
Handle
Registro en la Biblioteca Digital
Aporte de:Registro referencial: Solicitar el recurso aquí
LEADER 28281caa a22032177a 4500
001 PAPER-16281
003 AR-BaUEN
005 20230607131906.0
008 190411s2016 xx ||||fo|||| 00| 0 eng|d
024 7 |2 scopus  |a 2-s2.0-84988360266 
024 7 |2 cas  |a fluorine, 7782-41-4; Fluorine; Hydrocarbons, Fluorinated 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a OBCRA 
100 1 |a Yerien, D.E. 
245 1 0 |a Fluorination methods in drug discovery 
260 |b Royal Society of Chemistry  |c 2016 
270 1 0 |m Postigo, A.; Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires-CONICET, Junín 954, Argentina; email: apostigo@ffyb.uba.ar 
506 |2 openaire  |e Política editorial 
504 |a 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 
504 |a Harsanyi, A., Sandford, G., (2015) Green Chem., 17, pp. 2081-2086 
504 |a 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 
504 |a Gillis, E.P., Eastman, K.J., Hill, M.D., Donnelly, D.J., Meanwell, N.A., (2015) J. Med. Chem., 58, pp. 8315-8359 
504 |a Filler, R., Saha, R., (2009) Future Med. Chem., 1 (5), pp. 777-791 
504 |a Hagmann, W., (2008) J. Med. Chem., 51 (15), pp. 4359-4369 
504 |a Müller, K., Faeh, C., Diederich, F., (2007) Science, 317, pp. 1881-1886 
504 |a Bégué, J.-P., Bonnet-Delpon, D., (2006) J. Fluorine Chem., 127, pp. 992-1012 
504 |a Kirk, K.L., (2006) J. Fluorine Chem., 127, pp. 1013-1029 
504 |a Böhm, H.J., Banner, D., Bendels, S., Kansy, M., Kuhn, B., Müller, K., Obst-Sander, U., Stahl, M., (2004) ChemBioChem, 5, pp. 637-643 
504 |a Kirk, K.L., (2006) Curr. Top. Med. Chem., 6, pp. 1445-1543 
504 |a Gouverneur, V., Konrad, S., (2015) Chem. Rev., 115 (2), pp. 563-565 
504 |a O'Hagan, D., (2010) J. Fluorine Chem., 131, pp. 1071-1081 
504 |a Kirk, K.L., (2008) Org. Process Res. Dev., 12, pp. 305-321 
504 |a Purser, S., Moore, P.R., Swallow, S., Gouverneur, V., (2008) Chem. Soc. Rev., 37, pp. 320-330 
504 |a 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 
504 |a Ojima, I., (2009) Fluorine in Medicinal Chemistry and Chemical Biology, , ed., Blackwell Publishing, Ltd., John Wiley & Sons Publications 
504 |a Begué, J.-P., Bonnet-Delpon, D., (2008) Bioorganic and Medicinal Chemistry of Fluorine, , BioCIS-CNRS, Wiley 
504 |a 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 
504 |a Morgenthaler, M., Scheweizer, E., Hoffmann-Roder, A., Benini, F., Martin, R.E., Jaeschke, G., Wagner, B., Muller, K., (2007) ChemMedChem, 2, p. 1100 
504 |a Dawadi, S., Viswanathan, K., Boshoff, H.I., Barry, C.E., III, Aldrich, C.C., (2015) J. Org. Chem., 80, pp. 4835-4850 
504 |a 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 
504 |a 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 
504 |a 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 
504 |a 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 
504 |a Singh, R.P., Shreeve, J.-M., (2004) Acc. Chem. Res., 37, pp. 31-44 
504 |a Preshlock, S., Tredwell, M., Gouverneur, V., (2016) Chem. Rev., 116, pp. 719-766 
504 |a Buckingham, F., Gouverneur, V., (2016) Chem. Sci., 7, pp. 1645-1652 
504 |a Verhoog, S., Pfeifer, L., Khotavivattana, T., Calderwood, S., Collier, T.L., Wheelhouse, K., Tredwell, M., Gouverneur, V., (2016) Synlett, pp. 25-28 
504 |a 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 
504 |a 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 
504 |a 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 
504 |a 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 
504 |a Chansaenpak, K., Vabre, B., Gabbaï, F.P., (2016) Chem. Soc. Rev., 45, pp. 954-971 
504 |a Meyer, P., Westwell, A.D., (2015) Synthesis of Fluorinated Pharmaceuticals, pp. 6-17. , (10.4155/fseb2013.14.295) 
504 |a Rehm, T.H., (2016) Chem. Eng. Technol., 39, pp. 66-80 
504 |a Samori, C., Guerrini, A., Varchi, G., Fontana, G., Bombardelli, E., Tinelli, S., Beretta, G.L., Battaglia, A., (2009) J. Med. Chem., 52, p. 1029 
504 |a Kopyra, J., Kellerb, A., Bald, I., (2014) RSC Adv., 4, p. 6825 
504 |a Middleton, W.J., (1975) J. Org. Chem., 40, p. 574 
504 |a Hayashi, H., Sonoda, H., Fukumura, K., Nagata, T., (2002) Chem. Commun., p. 1618 
504 |a Lal, G.S., Pez, G.P., Pesaresi, R.J., Prozonic, F.M., Cheng, H., (1999) J. Org. Chem., 64, p. 7048 
504 |a Kremsner, J.M., Rack, M., Pilger, C., Kappe, C.O., (2009) Tetrahedron Lett., 50, pp. 3665-3668 
504 |a Schimler, S.D., Ryan, S.J., Bland, D.C., Anderson, J.E., Sanford, M.S., (2015) J. Org. Chem., 80, pp. 12137-12145 
504 |a Taylor, S.D., Kotoris, C.C., Hum, G., (1999) Tetrahedron, 55, pp. 12431-12477 
504 |a 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 
504 |a Banks, R.E., Besheesh, M.K., Mohialdin-Khaffaf, S.N., Sharif, I., (1996) J. Chem. Soc., Perkin Trans. 1, pp. 2069-2076 
504 |a Banks, R.E., (1998) J. Fluorine Chem., 87, pp. 1-17 
504 |a Sankar Lal, G., Pez, G.P., Syvre, R.G., (1996) Chem. Rev., 96 (5), pp. 1737-1756 
504 |a Umemoto, T., Kawada, K., Tomita, K., (1986) Tetrahedron Lett., 27, pp. 4465-4468 
504 |a Umemoto, T., Fukami, S., Tomizawa, G., Harasawa, K., Kawada, K., Tomia, K., (1990) J. Am. Chem. Soc., 112, pp. 8563-8575 
504 |a Umemoto, T., Tomizawa, G., (1995) J. Org. Chem., 60, pp. 6563-6570 
504 |a Shibata, N., Tarui, T., Doi, Y., Kirk, K.L., (2001) Angew. Chem., Int. Ed., 40, pp. 4461-4463. , Angew. Chem. 2001 113 4593 
504 |a Tréguier, B., Roche, S.P., (2014) Org. Lett., 16, pp. 278-281 
504 |a Differding, E., Ofner, H., (1991) Synlett, pp. 187-189 
504 |a Fukushi, K., Suzuki, S., Kamo, T., Tokunaga, E., Sumii, Y., Kagawa, T., Kawada, K., Shibata, N., (2016) Green Chem., 18, pp. 1864-1868 
504 |a Stavber, S., Pecn, T.S., Papez, M., Zupan, M., (1996) Chem. Commun., pp. 2247-2248 
504 |a Geary, G.C., Hope, E.G., Singh, K., Stuart, A.M., (2015) RSC Adv., 5, p. 16501 
504 |a Geary, G.C., Hope, E.G., Singh, K., Stuart, A.M., (2013) Chem. Commun., 49 (81), pp. 9263-9265 
504 |a Tang, P., Wang, W., Ritter, T., (2011) J. Am. Chem. Soc., 133, pp. 11482-11484 
504 |a Sladojevich, F., Arlow, S.I., Tang, P., Ritter, T., (2013) J. Am. Chem. Soc., 135, p. 2470 
504 |a Fujimoto, T., Becker, F., Ritter, T., (2014) Org. Process Res. Dev., 18, p. 1041 
504 |a Campbell, M.G., Ritter, T., (2014) Org. Process Res. Dev., 18, pp. 474-480 
504 |a Nielsen, M.K., Ugaz, C.R., Li, W., Doyle, A.G., (2015) J. Am. Chem. Soc., 137 (30), pp. 9571-9574 
504 |a Wenz, J., Rettenmeier, C.A., Wadepohl, H., Gade, L.H., (2016) Chem. Commun., 52, pp. 202-205 
504 |a 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 
504 |a Zeng, Y., Hu, J., (2015) Rep. Org. Chem., 5, pp. 19-39 
504 |a Cernak, T., Dykstra, K.D., Tyagarajan, S., Vachal, P., Krska, S.W., (2016) Chem. Soc. Rev., 45, pp. 546-576 
504 |a Champagne, P.A., Desroches, J., Hamel, J.-D., Vandamme, M., Paquin, J.-F., (2015) Chem. Rev., 115 (17), pp. 9073-9174 
504 |a Neumann, C.N., Ritter, T., (2015) Angew. Chem., Int. Ed., 54, pp. 2-8 
504 |a 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 
504 |a 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 
504 |a Hull, K.L., Anani, W.Q., Sanford, M.S., (2006) J. Am. Chem. Soc., 128, pp. 7134-7135 
504 |a Liu, B., Jiang, H.-Z., Shi, B.-F., (2014) J. Org. Chem., 79, pp. 1521-1526 
504 |a Ma, W., Ackermann, L., (2013) Chem.-Eur. J., 19, pp. 13925-13928 
504 |a Yao, J., Feng, R., Wu, Z., Liu, Z., Zhang, Y., (2013) Adv. Synth. Catal., 355, pp. 1517-1522 
504 |a Niu, L., Yang, H., Wang, R., Fu, H., (2012) Org. Lett., 14, pp. 2618-2621 
504 |a Ackermann, L., Diers, E., Manvar, A., (2012) Org. Lett., 14, pp. 1154-1157 
504 |a Chu, J.-H., Lin, P.-S., Wu, M.-J., (2010) Organometallics, 29, pp. 4058-4065 
504 |a Jia, X., Zhang, S., Wang, W., Luo, F., Cheng, J., (2009) Org. Lett., 11, pp. 3120-3123 
504 |a Kakiuchi, F., Igi, K., Matsumoto, M., Hayamizu, T., Chatani, N., Murai, S., (2002) Chem. Lett., 3, pp. 396-397 
504 |a Campbell, M.G., Ritter, T., (2015) Chem. Rev., 115, pp. 612-633 
504 |a Yang, X., Wu, T., Phipps, R.J., Toste, F.D., (2015) Chem. Rev., 115, pp. 826-870 
504 |a Hollingworth, C., Gouverneur, V., (2012) Chem. Commun., 48, pp. 2929-2942 
504 |a Furuya, T., Kamlet, A.S., Ritter, T., (2011) Nature, 473, pp. 470-477 
504 |a Grushin, V.V., (2010) Acc. Chem. Res., 43, pp. 160-171 
504 |a Watson, D.A., Su, M.J., Teverovskiy, G., Garcia-Fortanet, Y., Kinzel, T., Buchwald, S.L., (2009) Science, 325, p. 1661 
504 |a Ye, Y.D., Sanford, M.S., (2013) J. Am. Chem. Soc., 135 (12), pp. 4648-4651 
504 |a Furuya, T., Strom, A.E., Ritter, T., (2009) J. Am. Chem. Soc., 131, p. 1662 
504 |a Tang, P.P., Furuya, T., Ritter, T., (2010) J. Am. Chem. Soc., 132, p. 12150 
504 |a Furuya, T., Kaiser, H.M., Ritter, T., (2008) Angew. Chem., Int. Ed., 47, p. 5993 
504 |a Furuya, T., Ritter, T., (2009) Org. Lett., 11, p. 2860 
504 |a Tang, P.P., Ritter, T., (2011) Tetrahedron, 67, p. 4449 
504 |a 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 
504 |a Fier, P.S., Hartwig, J.F., (2012) J. Am. Chem. Soc., 134 (26), pp. 10795-10798 
504 |a Fier, P.S., Luo, J.W., Hartwig, J.F., (2013) J. Am. Chem. Soc., 135 (7), pp. 2552-2559 
504 |a 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 
504 |a Huang, S.M., (2009) Nature, 461, p. 614 
504 |a Yamada, S., Gavryushin, A., Knochel, P., (2010) Angew. Chem., Int. Ed., 49 (12), pp. 2215-2218 
504 |a Clark, J.H., Wails, D., Bastock, T.W., (1996) Aromatic Fluorination, , CRC Press, Boca Raton, FL 
504 |a Kuduk, S.D., DiPardo, R.M., Bock, M.G., (2005) Org. Lett., 7, p. 577 
504 |a 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 
504 |a Furuya, T., Klein, J.E.M.N., Ritter, T., (2010) Synthesis, p. 1804 
504 |a Miller, J., (1968) Aromatic Nucleophilic Substitution, , Elsevier, London 
504 |a Terrier, F., (2013) Modern Nucleophilic Aromatic Substitution, , Wiley-VCH, Weinheim, Germany 
504 |a Smith, D.A., Jones, R.M., (2008) Curr. Opin. Drug Discovery Dev., 11, pp. 72-79 
504 |a 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 
504 |a Fier, P.S., Hartwig, J.F., (2013) Science, 342, pp. 956-960 
504 |a Izawa, K., Acena, J.L., Wang, J., Soloshonok, V.A., Liu, H., (2016) Eur. J. Org. Chem., pp. 8-16 
504 |a Leahy, D.K., (2012) Org. Process Res. Dev., 16, pp. 244-249 
504 |a Serdyuk, O.V., Muzalevskiy, V.M., Nenajdenko, V.G., (2012) Synthesis, pp. 2115-2137 
504 |a Albertshofer, K., Mani, N.S., (2016) J. Org. Chem., 81 (3), pp. 1269-1276 
504 |a Jiang, Z., Ni, T., Wei, C., Tian, S., Li, Y., Dai, L., Liu, H., Zhang, D., (2013) Synlett, pp. 0215-0218 
504 |a Liu, P., Gao, Y., Gu, W., Shen, Z., Sun, P., (2015) J. Org. Chem., 80 (22), pp. 11559-11565 
504 |a Greenblatt, D.J., Roth, T., (2012) Expert Opin. Pharmacother., 13, p. 879 
504 |a Langer, S.Z., Arbilla, S., Benavides, J., Scatton, B., (1990) Adv. Biochem. Psychopharmacol., 46, p. 61 
504 |a Yamane, I., Hagino, H., Okano, T., Enokida, M., Yamasaki, D., Teshima, R., (2003) Arthritis Rheum., 48, p. 1732 
504 |a Mizushige, K., Ueda, T., Yukiiri, K., Suzuki, H., (2002) Cardiovasc. Drug Rev., 20, p. 163 
504 |a Katsura, Y., Nishino, S., Takasugi, H., (1991) Chem. Pharm. Bull., 39, p. 2937 
504 |a Nyffeler, P.T., Durón, S.G., Burkart, M.D., Vincent, S.P., Wong, C.H., (2005) Angew. Chem., Int. Ed., 44, p. 192 
504 |a Lin, R.-Y., Ding, S.-T., Shi, Z.-Z., Jiao, N., (2011) Org. Lett., 13, p. 4498 
504 |a Arcadi, A., Pietropaolo, E., Alvino, A., Michelet, V., (2013) Org. Lett., 15, p. 2766 
504 |a Yang, L., Ma, Y.-H., Song, F.-J., You, J.-S., (2014) Chem. Commun., 50, p. 3024 
504 |a Wang, M.-L., Liu, X.-X., Zhou, L., Zhu, J.-D., Sun, X., (2015) Org. Biomol. Chem., 13, p. 3190 
504 |a Breen, J.R., Sandford, G., Patel, B., Fray, J., (2015) Synlett, p. 51 
504 |a O'Leary, E.M., Jones, D.J., O'Donovan, F.P., O'Sullivan, T.P., (2015) J. Fluorine Chem., 176, pp. 93-120 
504 |a Zhang, H., Wang, B., Cui, L., Bao, X., Qu, J., Song, Y., (2015) Eur. J. Org. Chem., pp. 2143-2147 
504 |a Lam, Y.-H., Houk, K.N., (2014) J. Am. Chem. Soc., 136 (27), pp. 9556-9559 
504 |a Zhao, J.-F., Duan, X.-H., Yang, H., Guo, L.-N., (2015) J. Org. Chem., 80 (21), pp. 11149-11155 
504 |a 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 
504 |a Wolstenhulme, J.R., Gouverneur, V., (2014) Acc. Chem. Res., 47 (12), pp. 3560-3570 
504 |a 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 
504 |a 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 
504 |a Vasdev, N., Cao, P., Van Oosten, E.M., Wilson, A.A., Houle, S., Hao, G., Sun, X., Kulkarni, P., (2012) MedChemComm, 3, p. 1228 
504 |a Keri, R.S., Patil, S.A., Budagumpi, S., Srinivasa, B.M., (2015) Chem. Biol. Drug Des., 86 (4), pp. 410-423 
504 |a Wang, D., Sun, W., Chu, T., (2015) Eur. J. Org. Chem., pp. 4114-4118 
504 |a Isanbor, C., O'Hagan, D., (2006) J. Fluorine Chem., 127, pp. 303-319 
504 |a Codington, J.F., Doerr, I., Praag, D.V., Bendich, A., Fox, J.J., (1961) J. Am. Chem. Soc., 83, p. 5030 
504 |a Thibaudeau, C., Plavec, J., Chattopadhyaya, J., (1998) J. Org. Chem., 63, p. 4967 
504 |a Barchi, J.J., Jr., Jeong, L.-S., Siddiqui, S.A., Marquez, V.E., (1997) J. Biochem. Biophys. Methods, 34, p. 11 
504 |a Lee, K., Choi, Y., Gumina, G., Zhou, W., Schinazi, R.F., Chu, C.K., (2002) J. Med. Chem., 45, p. 1313 
504 |a Chong, Y., Gumina, G., Mathew, J.S., Schinazi, R.F., Chu, C.K., (2003) J. Med. Chem., 46, p. 3245 
504 |a Zhou, W., Gumina, G., Chong, Y., Wang, J., Schinazi, R.F., Chu, C.K., (2004) J. Med. Chem., 47, p. 3399 
504 |a Biffinger, J.C., Kim, H.W., DiMagno, S.G., (2004) ChemBioChem, 5, p. 622 
504 |a Hu, X.-G., Hunter, L., (2013) Beilstein J. Org. Chem., 9, pp. 2696-2708 
504 |a Shaw, S.J., Golf, D.A., Boralsky, L.A., Irving, M., Singh, R., (2013) J. Org. Chem., 78, pp. 8892-8897 
504 |a 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 
504 |a Nash, R.J., Kato, A., Yu, C.-Y., Fleet, G.W., (2011) Future Med. Chem., 3, pp. 1513-1521 
504 |a Prell, E., Korb, C., Kluge, R., Ströhl, D., Csuk, R., (2010) Arch. Pharm., 343, pp. 583-589 
504 |a Sankar Lal, G., (1995) Synth. Commun., 25 (5), pp. 725-737 
504 |a Wójtowicz-Rajche, H., (2012) J. Fluorine Chem., 143, pp. 11-48 
504 |a Brown, K., Dixey, M., Weymouth-Wilson, A., Linclau, B., (2014) Carbohydr. Res., 387, pp. 59-73 
504 |a Chen, P., Liu, G., (2015) Eur. J. Org. Chem., pp. 4295-4309 
504 |a Peifer, M., Berger, R., Shurtleff, V.W., Conrad, J.C., MacMillan, D.W.C., (2014) J. Am. Chem. Soc., 136, pp. 5900-5903 
504 |a Kwiatkowski, P., Beeson, T.D., Conrad, J.C., MacMillan, D.W., (2011) J. Am. Chem. Soc., 133, pp. 1738-1741 
504 |a 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 
504 |a Balzarini, J., Baba, M., Pauwels, R., Herdewijn, P., De Clercq, E., (1988) Biochem. Pharmacol., 37, pp. 2847-2856 
504 |a Bonate, P.L., Arthaud, L., Stephenson, K., Secrist, J.A., Weitman, S., (2006) Nat. Rev. Drug Discovery, 5, pp. 855-863 
504 |a Faderl, S., Gandhi, V., Keating, M.J., Jeha, S., Plunket, W., Kantarjian, H.M., (2005) Cancer, 103, pp. 1985-1995 
504 |a 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 
504 |a Ghosh, A.K., Lagisetty, P., Zajc, B., (2007) J. Org. Chem., 72, pp. 8222-8226 
504 |a Bertolini, G., Deleo, M., Frigerio, M., Losa, M., Velati, M., Process and intermediates for preparing emtricitabine (2011) US Pat., p. 7939660B2 
504 |a Koperniku, A., Liu, H., Hurley, P.B., (2016) Eur. J. Org. Chem., pp. 871-886 
504 |a 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 
504 |a 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 
504 |a Nodwell, M.B., Bagai, A., Halperin, S.D., Martin, R.E., Knust, H., Britton, R., (2015) Chem. Commun., 51 (59), pp. 11783-11786 
504 |a Liu, W., Groves, J.T., (2013) Angew. Chem., Int. Ed., 52, pp. 1-5 
504 |a Liu, W., Huang, X., Groves, J.T., (2013) Nat. Protoc., 8, pp. 2348-2354 
504 |a Liu, W., Huang, X., Cheng, M.J., Nielsen, R.J., Goddard, W.A., III, Groves, J.T., (2012) Science, 337, pp. 1322-1325 
504 |a Zhu, Q., Ji, D., Liang, T., Wang, X., Xu, Y., (2015) Org. Lett., 17, pp. 3798-3801 
504 |a Godard J-I, ; (1994) From Fluorine Med. 21st Century, Conf. Pap., , Strategies for introducing fluorine into corticosteroids Paper 10, 16 
504 |a O'Hagan, D., (2010) J. Fluorine Chem., 131, pp. 1071-1081 
504 |a Lee, H.J., Taraporewala, I.B., Heiman, A.S., (1989) Drugs Today, 25, pp. 577-588 
504 |a 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 
504 |a Ishida, N., Kawabata, N.O., Shimazaki, A., Hara, H., (2006) Cardiovasc. Drug Rev., 24, pp. 1-10 
504 |a Markovskii, L.N., Pashinnik, V.E., Kirsanov, A.V., (1973) Synthesis, p. 787 
504 |a Matsumura, Y., Mori, N., Nakano, T., Sasakura, H., Matsugi, T., Harab, H., Morizawa, Y., (2004) Tetrahedron Lett., 45, pp. 1527-1529 
504 |a Zhang, X., Guo, S., Tang, P., (2015) Org. Chem. Front., 2, pp. 806-810 
504 |a House, D.A., (1962) Chem. Rev., 62, p. 185 
504 |a 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 
504 |a 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 
504 |a Yin, F., Wang, Z., Li, Z., Li, C., (2012) J. Am. Chem. Soc., 134, p. 10401 
504 |a Barker, T.J., Boger, D.L., (2012) J. Am. Chem. Soc., 134, p. 13588 
504 |a Zhang, C., Li, Z., Zhu, L., Yu, L., Wang, Z., Li, C., (2013) J. Am. Chem. Soc., 135, p. 14082 
504 |a 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 
504 |a 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 
504 |a Baumann, M., Baxendale, I.R., Ley, S.V., (2011) Mol. Diversity, 15, pp. 613-630 
504 |a Stavber, G., Zupan, M., Stavber, S., (2009) Synlett, p. 589 
504 |a Ahlsten, N., Martin-Matute, B., (2011) Chem. Commun., 47, p. 8331 
504 |a Yang, Q., Mao, L., Yang, B., Yang, S., (2014) Org. Lett., 16, p. 3460 
504 |a Wang, W., Jasinski, W.J., Hammond, G.B., Xu, B., (2010) Angew. Chem., Int. Ed., 49, p. 7247 
504 |a 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 
504 |a Zhang, M., Gong, Y., Wang, W., (2013) Eur. J. Org. Chem., p. 7372 
504 |a Yang, H., Xu, B., Hammond, G.B., (2008) Org. Lett., 10, p. 5589 
504 |a Shibata, N., Ishimaru, T., Nakamura, S., Toru, T., (2007) J. Fluorine Chem., 128, pp. 469-483 
504 |a Ishimaru, T., Shibata, N., Horikawa, T., Yasuda, N., Nakamura, S., Toru, T., Shiro, M., (2008) Angew. Chem., Int. Ed., 120, pp. 4225-4229 
504 |a Shibata, N., Suzuki, E., Asahi, T., Shiro, M., (2001) J. Am. Chem. Soc., 123 (29), pp. 7001-7009 
504 |a Saadi, J., Wennemers, H., (2016) Nat. Chem., 8, pp. 276-280 
504 |a Dias, L.C., Vieiraand Eliezer, A.S., Barreiro, J., (2016) Org. Biomol. Chem., 14, pp. 2291-2296 
504 |a 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 
504 |a 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 
504 |a 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 
504 |a Surmont, R., Verniest, G., De Kimpe, N., (2010) Org. Lett., 12, pp. 4648-4651 
504 |a Fustero, S., Sanz-Cervera, J.F., Aceña, J.L., Sánchez-Roselló, M., (2009) Synlett, pp. 525-549 
504 |a 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 
504 |a Dong, X., Yang, W., Hu, W., Sun, J., (2015) Angew. Chem., Int. Ed., 54, pp. 660-663 
504 |a Cooper, J.B., (2002) Curr. Drug Targets, 3, p. 155 
504 |a Hu, X.-G., Lawer, A., Peterson, M.B., Iranmanesh, H., Ball, G.E., Hunter, L., (2016) Org. Lett., 18 (4), pp. 662-665 
504 |a Chen, G., Song, J., Yu, Y., Luo, X., Li, C., Huang, X., (2016) Chem. Sci., 7, pp. 1786-1790 
504 |a Kong, W., Merino, E., Nevado, C., (2014) Chimia, 68 (6), pp. 430-435 
504 |a Wu, L., Chen, P., Liu, G., (2016) Org. Lett., 18 (5), pp. 960-963 
504 |a Ulmer, A., Brunner, C., Arnold, A.M., Pçthig, A., Gulder, T., (2016) Chem.-Eur. J., 22, pp. 3660-3664 
504 |a Xu, T., Liu, G., (2012) Org. Lett., 14, pp. 5416-6519 
520 3 |a 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.  |l eng 
593 |a Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires-CONICET, Junín 954, Buenos Aires, CP 1113, Argentina 
593 |a Departamento de Química Orgánica, CIHIDECAR-CONICET, Pabellón II, Ciudad Universitaria, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, 1428, Argentina 
690 1 0 |a BIOACTIVITY 
690 1 0 |a BIOCHEMISTRY 
690 1 0 |a CHEMICAL BONDS 
690 1 0 |a ELECTRONEGATIVITY 
690 1 0 |a FLUORINATION 
690 1 0 |a HALOGENATION 
690 1 0 |a AROMATIC RINGS 
690 1 0 |a BIOLOGICALLY ACTIVE COMPOUNDS 
690 1 0 |a DRUG DISCOVERY 
690 1 0 |a FLUORINATION REACTIONS 
690 1 0 |a FLUORINE ATOMS 
690 1 0 |a FLUORINE SUBSTITUTION 
690 1 0 |a MEMBRANE PERMEABILITY 
690 1 0 |a PHARMACEUTICAL INDUSTRY 
690 1 0 |a FLUORINE 
690 1 0 |a FLUORINATED HYDROCARBON 
690 1 0 |a FLUORINE 
690 1 0 |a CHEMICAL STRUCTURE 
690 1 0 |a CHEMISTRY 
690 1 0 |a DRUG DEVELOPMENT 
690 1 0 |a HALOGENATION 
690 1 0 |a SYNTHESIS 
690 1 0 |a DRUG DISCOVERY 
690 1 0 |a FLUORINE 
690 1 0 |a HALOGENATION 
690 1 0 |a HYDROCARBONS, FLUORINATED 
690 1 0 |a MOLECULAR STRUCTURE 
650 1 7 |2 spines  |a CARBON 
700 1 |a Bonesi, S. 
700 1 |a Postigo, A. 
773 0 |d Royal Society of Chemistry, 2016  |g v. 14  |h pp. 8398-8427  |k n. 36  |p Org. Biomol. Chem.  |x 14770520  |w (AR-BaUEN)CENRE-2303  |t Organic and Biomolecular Chemistry 
856 4 1 |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-84988360266&doi=10.1039%2fc6ob00764c&partnerID=40&md5=1e484e5c3b76d82547b7e5d6f8f7c675  |y Registro en Scopus 
856 4 0 |u https://doi.org/10.1039/c6ob00764c  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_14770520_v14_n36_p8398_Yerien  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v14_n36_p8398_Yerien  |y Registro en la Biblioteca Digital 
961 |a paper_14770520_v14_n36_p8398_Yerien  |b paper  |c PE 
962 |a info:eu-repo/semantics/article  |a info:ar-repo/semantics/artículo  |b info:eu-repo/semantics/publishedVersion 
999 |c 77234