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Volumn 38, Issue 21, 2008, Pages 3823-3833

Kumada-Corriu cross coupling route to the anti-cancer agent combretastatin A-4

Author keywords

Anticancer; Cross coupling; Iron catalysis; Stilbene

Indexed keywords

ANTINEOPLASTIC AGENT; COMBRETASTATIN A4; GRIGNARD REAGENT; IRON; STILBENE DERIVATIVE;

EID: 54049114259     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802238692     Document Type: Article
Times cited : (23)

References (33)
  • 2
    • 0033844886 scopus 로고    scopus 로고
    • Combretastatin A-4 prodrug: A potent inhibitor of malignant hemangioendothelioma cell proliferation
    • Bohle, A. S.; Leuschner, I.; Kalthoff, H.; Henne-Bruns, D. Combretastatin A-4 prodrug: A potent inhibitor of malignant hemangioendothelioma cell proliferation. Int. J. Cancer 2000, 87, 838-843.
    • (2000) Int. J. Cancer , vol.87 , pp. 838-843
    • Bohle, A.S.1    Leuschner, I.2    Kalthoff, H.3    Henne-Bruns, D.4
  • 3
    • 0036282385 scopus 로고    scopus 로고
    • The biology of the combretastatins as tumour vascular targeting agents
    • Tozer, G. M.; Kanthou, C.; Parkins, C. S.; Hill, S. A. The biology of the combretastatins as tumour vascular targeting agents. Int. J. Exp. Pathol. 2002, 83, 21-38.
    • (2002) Int. J. Exp. Pathol , vol.83 , pp. 21-38
    • Tozer, G.M.1    Kanthou, C.2    Parkins, C.S.3    Hill, S.A.4
  • 5
    • 0141518578 scopus 로고    scopus 로고
    • Structural requirements for the interaction of combretastatins with tubulin: How important is the trimethoxy unit?
    • Gaukroger, K.; Hadfield, J. A.; Lawrence, N. J.; Nolan, S.; McGown, A. T. Structural requirements for the interaction of combretastatins with tubulin: How important is the trimethoxy unit? Org. Biomol. Chem. 2003, 1, 3033-3037.
    • (2003) Org. Biomol. Chem , vol.1 , pp. 3033-3037
    • Gaukroger, K.1    Hadfield, J.A.2    Lawrence, N.J.3    Nolan, S.4    McGown, A.T.5
  • 6
    • 0031980124 scopus 로고    scopus 로고
    • Antineoplastic agents 389: New syntheses of the combretastatin A-4 prodrug
    • (a) Pettit, G. R.; Rhodes, M. R. Antineoplastic agents 389: New syntheses of the combretastatin A-4 prodrug. Anti-Cancer Drug. Design 1998, 13, 183-191;
    • (1998) Anti-Cancer Drug. Design , vol.13 , pp. 183-191
    • Pettit, G.R.1    Rhodes, M.R.2
  • 8
    • 34948901109 scopus 로고    scopus 로고
    • Synthesis of biologically active heterocyclic stilbene and chalcone analogs of combretastatin
    • For reviews: a
    • For reviews: (a) Brown, T.; Holt, H.; Lee, M. Synthesis of biologically active heterocyclic stilbene and chalcone analogs of combretastatin. Top. Heterocycl. Chem. 2006, 2, 1-51;
    • (2006) Top. Heterocycl. Chem , vol.2 , pp. 1-51
    • Brown, T.1    Holt, H.2    Lee, M.3
  • 9
    • 18744379774 scopus 로고    scopus 로고
    • Pharmaceutical design of antimitotic agents based on combretastatins
    • (b) Hsieh, H. P.; Liuou, J. P.; Mahindroo, N. Pharmaceutical design of antimitotic agents based on combretastatins. Curr. Pharm. Design 2005, 11, 1665-1677;
    • (2005) Curr. Pharm. Design , vol.11 , pp. 1665-1677
    • Hsieh, H.P.1    Liuou, J.P.2    Mahindroo, N.3
  • 10
    • 1642542532 scopus 로고    scopus 로고
    • Combretastatin A-4 and its analogues as antineoplastic agents
    • (c) Dzierzbicka, K.; Kolodziejczyk, A. M. Combretastatin A-4 and its analogues as antineoplastic agents. Polish J. Chem. 2004, 78, 323-342;
    • (2004) Polish J. Chem , vol.78 , pp. 323-342
    • Dzierzbicka, K.1    Kolodziejczyk, A.M.2
  • 11
    • 0346433524 scopus 로고    scopus 로고
    • Cirla, A.; Mann, J. Combretastatins: From natural products to drug discovery. Nat. Prod. Rep. 2003, 20, 558-564;
    • (d) Cirla, A.; Mann, J. Combretastatins: From natural products to drug discovery. Nat. Prod. Rep. 2003, 20, 558-564;
  • 12
    • 0041421003 scopus 로고    scopus 로고
    • Combretastatin A-4 analogues as antimitotic antitumor agents
    • (e) Nam, N.-H. Combretastatin A-4 analogues as antimitotic antitumor agents. Curr. Med. Chem. 2003, 10, 1697-1722.
    • (2003) Curr. Med. Chem , vol.10 , pp. 1697-1722
    • Nam, N.-H.1
  • 13
    • 0032506604 scopus 로고    scopus 로고
    • The synthesis of alkenes via epiphosphonium species, 1: An anti-Wittig elimination
    • Lawrence, N. J.; Muhammad, F. The synthesis of alkenes via epiphosphonium species, 1: An anti-Wittig elimination. Tetrahedron 1998, 54, 15345-15360.
    • (1998) Tetrahedron , vol.54 , pp. 15345-15360
    • Lawrence, N.J.1    Muhammad, F.2
  • 15
    • 33748977642 scopus 로고    scopus 로고
    • Ethynylation of aryl halides by a modified Suzuki reaction: Application to the syntheses of combretastatin A-4, A-5 and lunularic acid
    • Fürstner, A.; Nikolakis, K. Ethynylation of aryl halides by a modified Suzuki reaction: Application to the syntheses of combretastatin A-4, A-5 and lunularic acid. Liebigs Ann. 1996, 2107-2113.
    • (1996) Liebigs Ann , pp. 2107-2113
    • Fürstner, A.1    Nikolakis, K.2
  • 17
    • 34249320150 scopus 로고    scopus 로고
    • A Ramberg-Bäcklund route to the stilbenoid anti-cancer agents combretastatin A-4 and DMU-212
    • Robinson, J. E.; Taylor, R. J. K. A Ramberg-Bäcklund route to the stilbenoid anti-cancer agents combretastatin A-4 and DMU-212. Chem. Commun. 2007, 1617-1619.
    • (2007) Chem. Commun , pp. 1617-1619
    • Robinson, J.E.1    Taylor, R.J.K.2
  • 18
    • 84918678077 scopus 로고
    • Nickel and palladium complex catalyzed cross-coupling reactions of organometallic reagents with organic halides
    • Reviews: a
    • Reviews: (a) Kumada, N. Nickel and palladium complex catalyzed cross-coupling reactions of organometallic reagents with organic halides. Pure Appl. Chem. 1980, 52, 669-679;
    • (1980) Pure Appl. Chem , vol.52 , pp. 669-679
    • Kumada, N.1
  • 21
    • 0000259867 scopus 로고
    • Nickel-phosphine complex-catalyzed Grignard coupling. I. Cross-coupling of alkyl, aryl, and alkenyl Grignard reagents with aryl and alkenyl halides: General scope and limitations
    • (a) Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S.-I.; Nakajima, I.; Minato, A.; Kumada, M. Nickel-phosphine complex-catalyzed Grignard coupling. I. Cross-coupling of alkyl, aryl, and alkenyl Grignard reagents with aryl and alkenyl halides: General scope and limitations. Bull. Soc. Chem. Jpn. 1976, 49, 1958-1969;
    • (1976) Bull. Soc. Chem. Jpn , vol.49 , pp. 1958-1969
    • Tamao, K.1    Sumitani, K.2    Kiso, Y.3    Zembayashi, M.4    Fujioka, A.5    Kodama, S.-I.6    Nakajima, I.7    Minato, A.8    Kumada, M.9
  • 22
    • 54049128617 scopus 로고
    • Synthesis of styrenes by cross-coupling substituted phenylmagnesium bromides with vinyl bromide in the presence of a nickel complex
    • (b) Lebedev, S. A.; Sorokina, R. S.; Petrov, E. S. Synthesis of styrenes by cross-coupling substituted phenylmagnesium bromides with vinyl bromide in the presence of a nickel complex. Russ. J. Org. Chem. 1989, 25, 2026-2027;
    • (1989) Russ. J. Org. Chem , vol.25 , pp. 2026-2027
    • Lebedev, S.A.1    Sorokina, R.S.2    Petrov, E.S.3
  • 23
    • 0000957922 scopus 로고
    • Iron catalyzed cross-coupling reactions: Synthesis of arylethenes
    • (c) Molander, G. A.; Rahn, B. J.; Shubert, D. C.; Bonde, S. E. Iron catalyzed cross-coupling reactions: Synthesis of arylethenes. Tetrahedron Lett. 1983, 24, 5449-5452.
    • (1983) Tetrahedron Lett , vol.24 , pp. 5449-5452
    • Molander, G.A.1    Rahn, B.J.2    Shubert, D.C.3    Bonde, S.E.4
  • 24
    • 9744259538 scopus 로고    scopus 로고
    • For a review of the synthesis of stilbenes: Ferré: Filmon, K.; Delaude, L.; Demonceau, A.; Noels, A. F. Catalytic methods for the synthesis of stilbenes with an emphasis on their phytoalexins. Coord. Chem. Rev. 2004, 248, 2323-2336.
    • For a review of the synthesis of stilbenes: Ferré: Filmon, K.; Delaude, L.; Demonceau, A.; Noels, A. F. Catalytic methods for the synthesis of stilbenes with an emphasis on their phytoalexins. Coord. Chem. Rev. 2004, 248, 2323-2336.
  • 25
    • 33646071571 scopus 로고    scopus 로고
    • 4: Enantioselective synthesis of (R)-baclofen and (R)-rolipram
    • 4: Enantioselective synthesis of (R)-baclofen and (R)-rolipram. Tetrahedron 2006, 62, 4907-4916.
    • (2006) Tetrahedron , vol.62 , pp. 4907-4916
    • Paraskar, A.S.1    Sudalai, A.2
  • 27
    • 0033035311 scopus 로고    scopus 로고
    • 2-Arylvinylation of 1-methylindole by palladium-catalyzed cross-coupling reactions
    • Herz, H.-G.; Queiroz, M. J. R. P.; Maas, G. 2-Arylvinylation of 1-methylindole by palladium-catalyzed cross-coupling reactions. Synthesis 1999, 1013-1016.
    • (1999) Synthesis , pp. 1013-1016
    • Herz, H.-G.1    Queiroz, M.J.R.P.2    Maas, G.3
  • 28
    • 0001051635 scopus 로고    scopus 로고
    • A mild procedure for the stereospecific transformation of trans cinnamic acid derivatives to cis β-bromostyrenes
    • Kim, S. H.; Wei, H.-X.; Willis, S.; Li, G. A mild procedure for the stereospecific transformation of trans cinnamic acid derivatives to cis β-bromostyrenes. Synth. Commun. 1999, 29, 4179-4185.
    • (1999) Synth. Commun , vol.29 , pp. 4179-4185
    • Kim, S.H.1    Wei, H.-X.2    Willis, S.3    Li, G.4
  • 29
    • 19344365167 scopus 로고    scopus 로고
    • Synthesis of (Z)-1-bromo-1-alkenes and terminal alkynes from anti-2,3-dibromoalkanoic acids by microwave-induced reaction
    • Kuang, C.; Yang, Q.; Senboku, H.; Tokuda, M. Synthesis of (Z)-1-bromo-1-alkenes and terminal alkynes from anti-2,3-dibromoalkanoic acids by microwave-induced reaction. Tetrahedron 2005, 61, 4043-4052.
    • (2005) Tetrahedron , vol.61 , pp. 4043-4052
    • Kuang, C.1    Yang, Q.2    Senboku, H.3    Tokuda, M.4
  • 30
    • 0010918071 scopus 로고
    • Reactivity of ethylenic compounds, 42: The multipathway mechanism in styrene bromination: Competition between bromonium and carbonium ion intermediates
    • (a) Ruasse, M. F.; Argile, A.; Dubois, J. E. Reactivity of ethylenic compounds, 42: The multipathway mechanism in styrene bromination: Competition between bromonium and carbonium ion intermediates. J. Am. Chem. Soc. 1978, 100, 7645-7652;
    • (1978) J. Am. Chem. Soc , vol.100 , pp. 7645-7652
    • Ruasse, M.F.1    Argile, A.2    Dubois, J.E.3
  • 31
    • 84879134314 scopus 로고
    • The stereochemistry of electrophilic additions to olefins and acetylenes
    • (b) Fahey, R. C. The stereochemistry of electrophilic additions to olefins and acetylenes. Top. Stereochem. 1968, 3, 237-342.
    • (1968) Top. Stereochem , vol.3 , pp. 237-342
    • Fahey, R.C.1
  • 32
    • 0031871453 scopus 로고    scopus 로고
    • Highly stereo- and chemoselective iron-catalyzed alkenylation of organomagnesium compounds
    • (a) Cahiez, G.; Avedissian, H. Highly stereo- and chemoselective iron-catalyzed alkenylation of organomagnesium compounds. Synthesis 1998, 1199-1205;
    • (1998) Synthesis , pp. 1199-1205
    • Cahiez, G.1    Avedissian, H.2
  • 33
    • 0035212248 scopus 로고    scopus 로고
    • Fe(III)-catalyzed cross-coupling between functionalized arylmagnesium compounds and alkenyl halides
    • (b) Dohle, W.; Kopp, F.; Cahiez, G.; Knochel, P. Fe(III)-catalyzed cross-coupling between functionalized arylmagnesium compounds and alkenyl halides. Synlett. 2001, 1901-1904.
    • (2001) Synlett , pp. 1901-1904
    • Dohle, W.1    Kopp, F.2    Cahiez, G.3    Knochel, P.4


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