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Synthesis 2008(24): 4007-4011
DOI: 10.1055/s-0028-1083239
DOI: 10.1055/s-0028-1083239
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkMulticomponent Reactions as a Powerful Tool for Generic Drug Synthesis
Weitere Informationen
Received
11 April 2008
Publikationsdatum:
01. Dezember 2008 (online)
Publikationsverlauf
Publikationsdatum:
01. Dezember 2008 (online)

Abstract
Multicomponent reactions (MCRs) are not only a powerful tool for drug discovery, they also represent an excellent methodology for synthesis rationalization. Here we wish to illustrate the potential of MCRs in the production of generic drugs by synthesizing, in racemic form, the antiplatelet agent clopidogrel and the non-steroidal antiandrogen bicalutamide, using Ugi, Petasis and Passerini reactions.
Key words
multicomponent reactions - drugs - cleavage - clopidogrel - bicalutamide
- 1a
Dömling A.Ugi I. Angew. Chem. Int. Ed. 2000, 39: 3168Reference Ris Wihthout Link - 1b
Dömling A. Chem. Rev. 2006, 106: 17Reference Ris Wihthout Link - 2
Hulme C. In Multicomponent ReactionsZhu J.Bienayme H. Wiley-VCH; Weinheim: 2005.Reference Ris Wihthout Link - 3a
Rossen K.Pye PJ.DiMichele LM.Volante RP.Reider PJ. Tetrahedron Lett. 1998, 39: 6823Reference Ris Wihthout Link - 3b
Askin D.Eng KK.Rossen K.Purick RM.Wells KM.Volante RP.Reider PJ. Tetrahedron Lett. 1994, 35: 673Reference Ris Wihthout Link - 4
Endo A.Yanagisawa A.Abe M.Tohma S.Kan T.Fukuyama T. J. Am. Chem. Soc. 2002, 124: 6552 - 5a
Gurbel PA.O’Connor CM.Cummings CC.Serebruany VL. Pharm. Res. 1999, 40: 107Reference Ris Wihthout Link - 5b
Jacobson AK. Best Pract. Res. Clin. Haematol. 2004, 17: 55Reference Ris Wihthout Link - 6a
Ugi I.Meyer R.Fetzer U.Steinbrückner C. Angew. Chem. 1959, 71: 386Reference Ris Wihthout Link - 6b
Ugi I. Angew. Chem., Int. Ed. Engl. 1962, 1: 8Reference Ris Wihthout Link - 6c
Dömling A.Ugi I. Angew. Chem. 2000, 112: 3300Reference Ris Wihthout Link - 7
Keating TA.Armstromg W. J. Am. Chem. Soc. 1996, 118: 2574 - 8
Petasis NA.Akritopoulou I. Tetrahedron Lett. 1993, 34: 583 - 9
Petasis NA.Zavialov IA. J. Am. Chem. Soc. 1997, 119: 445 - 10
Lindhorst T.Bock H.Ugi I. Tetrahedron 1999, 55: 7411 - 11a
Eliel EL.Fisk MT.Prosser T. Org. Synth. Coll. Vol. IV John Wiley & Sons; London: 1963. p.169Reference Ris Wihthout Link - 11b
Aubert D,Ferrand C, andMaffrand J.-P. inventors; French Patent FR2530247.Reference Ris Wihthout Link - 11c
Badorc A, andFrehel D. inventors; US Patent 4847265.Reference Ris Wihthout Link - 11d
Tucker H. inventors; US Patent 4636505.Reference Ris Wihthout Link - 11e
Soeroes B,Tuba Z,Galik G,Bor A,Demeter A,Trischler F,Horvath J, andBrlik J. inventors; US Patent 7199257.Reference Ris Wihthout Link - 12a
Pirrung MC.Ghorai S. J. Am. Chem. Soc. 2006, 128: 11772Reference Ris Wihthout Link - 12b
Kreye O.Westermann B.Wessjohann LA. Synlett 2007, 3188Reference Ris Wihthout Link - 12c
Gilley CB.Buller MJ.Kobayashi Y. Org. Lett. 2007, 9: 3631Reference Ris Wihthout Link - 13a
Masiello D.Cheng S.Bubley GJ.Lu ML.Balk SP. J. Biol. Chem. 2002, 29: 26321Reference Ris Wihthout Link - 13b
Hodgson MC.Astapova I.Hollenberg AN.Balk SP. Cancer Res. 2007, 67: 8388Reference Ris Wihthout Link - 14a
Passerini M. Gazz. Chim. Ital. 1921, 51: 126Reference Ris Wihthout Link - 14b
Passerini M. Gazz. Chim. Ital. 1921, 51: 181Reference Ris Wihthout Link - 15a
Schiess M.Seebach D. Helv. Chim. Acta 1983, 66: 1618Reference Ris Wihthout Link - 15b
Seebach D.Adam G.Gees T.Schiess M.Weigand W. Chem. Ber. 1988, 121: 507Reference Ris Wihthout Link - 15c
Seebach D.Beck AK.Schiess M.Widler L.Wonnacott A. Pure Appl. Chem. 1983, 55: 1807Reference Ris Wihthout Link - 16
Carofiglio T.Cozzi PG.Floriani C. Organometallics 1993, 12: 2726 - 17
Semple JE.Owens TD.Nguyen K.Levy OE. Org. Lett. 2000, 2: 2769 - 18
James KD.Ekwuribe NN. Tetrahedron 2002, 58: 5905 - 19
James KD.Ekwuribe NN. Synthesis 2002, 850 - 20
Obrecht R.Herrmann R.Ugi I. Synthesis 1985, 400