메뉴 건너뛰기




Volumn 46, Issue 17, 2003, Pages 3623-3630

Synthesis of novel macrocyclic docetaxel analogues. Influence of their macrocyclic ring size on tubulin activity

Author keywords

[No Author keywords available]

Indexed keywords

DOCETAXEL; MACROCYCLIC COMPOUND; PACLITAXEL; TAXOID; TUBULIN;

EID: 0043234178     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030770w     Document Type: Article
Times cited : (27)

References (31)
  • 2
    • 0018387446 scopus 로고
    • Promotion of microtubule assembly in vitro by Taxol
    • Schiff, P. B.; Fant, J.; Horwitz, S. B. Promotion of Microtubule Assembly in vitro by Taxol. Nature 1979, 277, 665-667.
    • (1979) Nature , vol.277 , pp. 665-667
    • Schiff, P.B.1    Fant, J.2    Horwitz, S.B.3
  • 3
    • 0015211527 scopus 로고
    • Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from taxus brevifolia
    • Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. Plant Antitumor Agents. VI. The Isolation and Structure of Taxol, a Novel Antileukemic and Antitumor Agent from Taxus brevifolia. J. Am. Chem. Soc. 1971, 93, 2325-2327
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 2325-2327
    • Wani, M.C.1    Taylor, H.L.2    Wall, M.E.3    Coggon, P.4    McPhail, A.T.5
  • 4
    • 0000052734 scopus 로고
    • Taxol and taxotere: Discovery, chemistry and structure-activity relationships
    • For a review, see the following. Guénard, D.; Guéritte-Voegelein, F.; Potier, P. Taxol and Taxotere: Discovery, Chemistry and Structure-Activity Relationships. Acc. Chem. Res. 1993, 26, 160-167.
    • (1993) Acc. Chem. Res. , vol.26 , pp. 160-167
    • Guénard, D.1    Guéritte-Voegelein, F.2    Potier, P.3
  • 5
    • 0003469887 scopus 로고
    • Suffness, M., Ed.; CRC Press: Boca Raton, FL
    • For general reviews on taxoid chemistry, see the following. (a) Taxol: Science and Applications; Suffness, M., Ed.; CRC Press: Boca Raton, FL, 1995. (b) Taxane Anticancer Agents: Basic Science and Current Status; Georg, I. G., Chen, T. T., Ojima, I., Vyas, D. M., Eds.; ACS Symposium Series 583; American Chemical Society, Washington, DC, 1995. (c) The Chemistry and Pharmacology of Taxol and Its Derivatives; Farina, V., Ed.; Elsevier: Amsterdam, 1995. (d) Kingston, D. G. I.; Yuan, H.; Jagtap, P. J.; Samala, L. The Chemistry of Taxol and Related Taxoids. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch., Eds; Springer-Verlag: Vienna and New York, 2002; Vol. 84.
    • (1995) Taxol: Science and Applications
  • 6
    • 0042891853 scopus 로고
    • Georg, I. G., Chen, T. T., Ojima, I., Vyas, D. M., Eds.; ACS Symposium Series 583; American Chemical Society, Washington, DC
    • For general reviews on taxoid chemistry, see the following. (a) Taxol: Science and Applications; Suffness, M., Ed.; CRC Press: Boca Raton, FL, 1995. (b) Taxane Anticancer Agents: Basic Science and Current Status; Georg, I. G., Chen, T. T., Ojima, I., Vyas, D. M., Eds.; ACS Symposium Series 583; American Chemical Society, Washington, DC, 1995. (c) The Chemistry and Pharmacology of Taxol and Its Derivatives; Farina, V., Ed.; Elsevier: Amsterdam, 1995. (d) Kingston, D. G. I.; Yuan, H.; Jagtap, P. J.; Samala, L. The Chemistry of Taxol and Related Taxoids. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch., Eds; Springer-Verlag: Vienna and New York, 2002; Vol. 84.
    • (1995) Taxane Anticancer Agents: Basic Science and Current Status
  • 7
    • 0003897919 scopus 로고
    • Farina, V., Ed.; Elsevier: Amsterdam
    • For general reviews on taxoid chemistry, see the following. (a) Taxol: Science and Applications; Suffness, M., Ed.; CRC Press: Boca Raton, FL, 1995. (b) Taxane Anticancer Agents: Basic Science and Current Status; Georg, I. G., Chen, T. T., Ojima, I., Vyas, D. M., Eds.; ACS Symposium Series 583; American Chemical Society, Washington, DC, 1995. (c) The Chemistry and Pharmacology of Taxol and Its Derivatives; Farina, V., Ed.; Elsevier: Amsterdam, 1995. (d) Kingston, D. G. I.; Yuan, H.; Jagtap, P. J.; Samala, L. The Chemistry of Taxol and Related Taxoids. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch., Eds; Springer-Verlag: Vienna and New York, 2002; Vol. 84.
    • (1995) The Chemistry and Pharmacology of Taxol and Its Derivatives
  • 8
    • 0036048410 scopus 로고    scopus 로고
    • The chemistry of taxol and related taxoids
    • Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch., Eds; Springer-Verlag: Vienna and New York
    • For general reviews on taxoid chemistry, see the following. (a) Taxol: Science and Applications; Suffness, M., Ed.; CRC Press: Boca Raton, FL, 1995. (b) Taxane Anticancer Agents: Basic Science and Current Status; Georg, I. G., Chen, T. T., Ojima, I., Vyas, D. M., Eds.; ACS Symposium Series 583; American Chemical Society, Washington, DC, 1995. (c) The Chemistry and Pharmacology of Taxol and Its Derivatives; Farina, V., Ed.; Elsevier: Amsterdam, 1995. (d) Kingston, D. G. I.; Yuan, H.; Jagtap, P. J.; Samala, L. The Chemistry of Taxol and Related Taxoids. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch., Eds; Springer-Verlag: Vienna and New York, 2002; Vol. 84.
    • (2002) Progress in the Chemistry of Organic Natural Products , vol.84
    • Kingston, D.G.I.1    Yuan, H.2    Jagtap, P.J.3    Samala, L.4
  • 9
    • 0035834521 scopus 로고    scopus 로고
    • Refined structure of the alpha beta tubulin at 3.5 A resolution
    • Löwe, J.; Li, H.; Downing, K. H.; Nogales, E. Refined Structure of the Alpha Beta Tubulin at 3.5 A Resolution. J. Mol. Biol. 2001, 313, 1045-1057.
    • (2001) J. Mol. Biol. , vol.313 , pp. 1045-1057
    • Löwe, J.1    Li, H.2    Downing, K.H.3    Nogales, E.4
  • 11
    • 0027730478 scopus 로고
    • A "hydrophobic collapse" of taxol and taxotere solution conformations in mixture of water and organic solvent
    • (a) Vander Velde, D. G.; Georg, G. I.; Grunewald, G. L.; Gunn, C. W.; Mitscher, L. A. A "Hydrophobic Collapse" of Taxol and Taxotere Solution Conformations in Mixture of Water and Organic Solvent. J. Am. Chem. Soc. 1993, 115, 11650-11651.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 11650-11651
    • Vander Velde, D.G.1    Georg, G.I.2    Grunewald, G.L.3    Gunn, C.W.4    Mitscher, L.A.5
  • 12
    • 0027305373 scopus 로고
    • NMR molecular modelling study of the conformation of taxol and its side chain methyl ester in aqueous and non-aqueous solution
    • (b) Williams, H. J.; Scott, A. I.; Dieden, R. A.; Swindell, C. S.; Chirlian, L. E.; Francl, M. M.; Heerding, J. M.; Krausss, N. E. NMR and Molecular Modelling Study of the Conformation of Taxol and Its Side Chain Methyl Ester in Aqueous and Non-Aqueous Solution. Tetrahedron 1993, 49, 6545-6560.
    • (1993) Tetrahedron , vol.49 , pp. 6545-6560
    • Williams, H.J.1    Scott, A.I.2    Dieden, R.A.3    Swindell, C.S.4    Chirlian, L.E.5    Francl, M.M.6    Heerding, J.M.7    Krausss, N.E.8
  • 16
    • 0035942226 scopus 로고    scopus 로고
    • The binding conformation of taxol in β-tubulin: A model based on electron crystallographic density
    • Snyder, J. P.; Nettles, J. H.; Cornett, B.; Downing, K. H.; Nogales, E. The Binding Conformation of Taxol in β-Tubulin: A Model Based on Electron Crystallographic Density. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 5312-5316.
    • (2001) Proc. Natl. Acad. Sci. U.S.A. , vol.98 , pp. 5312-5316
    • Snyder, J.P.1    Nettles, J.H.2    Cornett, B.3    Downing, K.H.4    Nogales, E.5
  • 17
    • 0033581642 scopus 로고    scopus 로고
    • Conformationally restricted paclitaxel analogues: Macrocyclic mimics of the "hydrophobic collapse" conformation
    • (a) Boge, T. C.; Wu, Z.-J.; Himes, R. H.; Vander Velde, D. G.; Georg, G. I. Conformationally Restricted Paclitaxel Analogues: Macrocyclic Mimics of the "Hydrophobic Collapse" Conformation. Bioorg. Med. Chem. Lett. 1999, 9, 3047-3052.
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 3047-3052
    • Boge, T.C.1    Wu, Z.-J.2    Himes, R.H.3    Vander Velde, D.G.4    Georg, G.I.5
  • 19
    • 0034616754 scopus 로고    scopus 로고
    • Macrocycle formation by ring-closing metathesis. Application to the syntheses of novel macrocyclic taxoids
    • (c) Ojima, I.; Lin, S.; Inoue, T.; Miller, M. L.; Borella, C. P.; Geng, X.; Walsh, J. J. Macrocycle Formation by Ring-Closing Metathesis. Application to the Syntheses of Novel Macrocyclic Taxoids. J. Am. Chem. Soc. 2000, 122, 5343-5353.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 5343-5353
    • Ojima, I.1    Lin, S.2    Inoue, T.3    Miller, M.L.4    Borella, C.P.5    Geng, X.6    Walsh, J.J.7
  • 22
    • 0037059894 scopus 로고    scopus 로고
    • Design synthesis and biological activity of novel C2-C3′ N-linked macrocyclic taxoids
    • (f) Ojima, I.; Geng, X.; Lin, S.; Pera, P.; Bernacki, R. J. Design Synthesis and Biological Activity of Novel C2-C3′ N-Linked Macrocyclic Taxoids. Bioorg. Med. Chem. Lett. 2002, 12, 349-352.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 349-352
    • Ojima, I.1    Geng, X.2    Lin, S.3    Pera, P.4    Bernacki, R.J.5
  • 24
    • 0032580376 scopus 로고    scopus 로고
    • Recent advances in olefin metathesis and its application in organic synthesis
    • Grubbs, R. H.; Chang, S. Recent Advances in Olefin Metathesis and Its Application in Organic Synthesis. Tetrahedron 1998, 54, 4413-4450.
    • (1998) Tetrahedron , vol.54 , pp. 4413-4450
    • Grubbs, R.H.1    Chang, S.2
  • 25
    • 0001318007 scopus 로고
    • Relationships between the structures of taxol and baccatin III derivatives and their in vitro action on the disassembly of mammalian brain and physarum amoebal microtubules
    • Lataste, H.; Sénihl, V.; Wright, M.; Guénard, D.; Potier, P. Relationships between the Structures of Taxol and Baccatin III Derivatives and Their in Vitro Action on the Disassembly of Mammalian Brain and Physarum Amoebal Microtubules. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 4090-4094.
    • (1984) Proc. Natl. Acad. Sci. U.S.A. , vol.81 , pp. 4090-4094
    • Lataste, H.1    Sénihl, V.2    Wright, M.3    Guénard, D.4    Potier, P.5
  • 26
    • 0028293455 scopus 로고
    • Synthesis and biological activity of methyl-D-pyranoside derivatives of mercaptopurine and mercaptopyrimidine
    • Da Silva, A. D.; Machado, A. S.; Tempête, C.; Robert-Gero, M. Synthesis and Biological Activity of Methyl-D-Pyranoside Derivatives of Mercaptopurine and Mercaptopyrimidine. Eur. J. Med. Chem. 1994, 29, 149-152.
    • (1994) Eur. J. Med. Chem. , vol.29 , pp. 149-152
    • Da Silva, A.D.1    Machado, A.S.2    Tempête, C.3    Robert-Gero, M.4
  • 29
    • 0036086206 scopus 로고    scopus 로고
    • The solid state, solution and tubulin-bound conformations of agents that promote microtubule stabilization
    • Jiménez-Barbero, J.; Amat-Guerri, F.; Snyder, J. P. The Solid State, Solution and Tubulin-Bound Conformations of Agents That Promote Microtubule Stabilization. Curr. Med. Chem.: Anti-Cancer Agents 2002, 2, 91-122.
    • (2002) Curr. Med. Chem.: Anti-Cancer Agents , vol.2 , pp. 91-122
    • Jiménez-Barbero, J.1    Amat-Guerri, F.2    Snyder, J.P.3
  • 30
    • 0042891852 scopus 로고    scopus 로고
    • Calculated conformer energies for organic molecules with multiple polar functionalities are method dependent: Taxol (case study)
    • Lakdawala, A.; Wang, M.; Nevins, N.; Liotta, D. C.; Rusinska-Roszak, D.; Lozynski, M.; Snyder, J. P. Calculated conformer energies for organic molecules with multiple polar functionalities are method dependent: Taxol (case study). BMC Chem. Biol. 2001, 1-2 (available from http://www.biomedcentral.com/1472-6769/1/2).
    • (2001) BMC Chem. Biol.
    • Lakdawala, A.1    Wang, M.2    Nevins, N.3    Liotta, D.C.4    Rusinska-Roszak, D.5    Lozynski, M.6    Snyder, J.P.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.