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Volumn 41, Issue 19, 1998, Pages 3715-3726

Synthesis and biological evaluation of 2-acyl analogues of paclitaxel (Taxol)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; PACLITAXEL DERIVATIVE;

EID: 15144350837     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980229d     Document Type: Article
Times cited : (76)

References (55)
  • 1
    • 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
  • 2
    • 0018387446 scopus 로고
    • Promotion of Microtubule Assembly in Vitro by Taxol
    • (a) 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
    • 0021229643 scopus 로고
    • Taxol: An Antimitotic Agent with a New Mechanism of Action
    • (b) Manfredi, J. J.; Horwitz, S. B. Taxol: An Antimitotic Agent with a New Mechanism of Action. Pharmacol. Ther. 1984, 25, 83-125.
    • (1984) Pharmacol. Ther. , vol.25 , pp. 83-125
    • Manfredi, J.J.1    Horwitz, S.B.2
  • 4
    • 85127687495 scopus 로고
    • Taxol: Clinical Results and Current Issues in Development
    • Suffness, M., Ed.; CRC Press: Boca Raton, FL
    • (a) Arbuck, S. G.; Blaylock, B. A. Taxol: Clinical Results and Current Issues in Development. In Taxol: Science and Applications; Suffness, M., Ed.; CRC Press: Boca Raton, FL, 1995; pp 379-415.
    • (1995) Taxol: Science and Applications , pp. 379-415
    • Arbuck, S.G.1    Blaylock, B.A.2
  • 5
    • 0001881989 scopus 로고
    • Current Status of Clinical Trials with Paclitaxel and Docetaxel
    • Georg, G. I., Chen, T. T., Ojima, I., Vyas, D. M., Eds.; ACS Symposium Series 583; American Chemical Society: Washington, DC
    • (b) Holmes, F. A.; Kudelka, A. P.; Kavanagh, J. J.; Huber, M. H.; Ajani, J. A.; Valero, V. Current Status of Clinical Trials with Paclitaxel and Docetaxel. In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I., Chen, T. T., Ojima, I., Vyas, D. M., Eds.; ACS Symposium Series 583; American Chemical Society: Washington, DC, 1994; pp 31-57.
    • (1994) Taxane Anticancer Agents: Basic Science and Current Status , pp. 31-57
    • Holmes, F.A.1    Kudelka, A.P.2    Kavanagh, J.J.3    Huber, M.H.4    Ajani, J.A.5    Valero, V.6
  • 6
    • 0027365319 scopus 로고
    • An Overview of Experience with Taxol (Paclitaxel) in the U.S.A
    • Donehower, R. C.; Rowinsky, E. K. An Overview of Experience with Taxol (Paclitaxel) in the U.S.A. Cancer. Treat. Rev. 1993, 19 (Suppl.), 63-78.
    • (1993) Cancer. Treat. Rev. , vol.19 , Issue.SUPPL. , pp. 63-78
    • Donehower, R.C.1    Rowinsky, E.K.2
  • 8
    • 0001843250 scopus 로고
    • Paclitaxel Structure-Activity Relationships and Core Skeletal Rearrangements
    • Georg, G. I., Chen, T. T., Ojima, I., Vyas, D. M., Eds.; ACS Symposium Series 583; American Chemical Society: Washington, DC
    • (a) Chen, S.-H.; Farina, V. Paclitaxel Structure-Activity Relationships and Core Skeletal Rearrangements. In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I., Chen, T. T., Ojima, I., Vyas, D. M., Eds.; ACS Symposium Series 583; American Chemical Society: Washington, DC, 1994; pp 247-261.
    • (1994) Taxane Anticancer Agents: Basic Science and Current Status , pp. 247-261
    • Chen, S.-H.1    Farina, V.2
  • 10
    • 0026344562 scopus 로고
    • The Chemistry of Taxol
    • Kingston, D. G. I. The Chemistry of Taxol. Pharmacol. Ther. 1991, 52, 1-34.
    • (1991) Pharmacol. Ther. , vol.52 , pp. 1-34
    • Kingston, D.G.I.1
  • 11
    • 0028452906 scopus 로고
    • Taxol: The Chemistry and Structure-Activity Relationships of a Novel Anticancer Agent
    • Kingston, D. G. I. Taxol: the Chemistry and Structure-Activity Relationships of a Novel Anticancer Agent. Trends Biotechnol. 1994, 12, 222-227.
    • (1994) Trends Biotechnol. , vol.12 , pp. 222-227
    • Kingston, D.G.I.1
  • 12
    • 0000655508 scopus 로고
    • Recent Advances in the Chemistry and Structure-Activity Relationships of Paclitaxel
    • Georg, G. I., Chen. T. T., Ojima, I., Vyas, D. M., Eds.; ACS Symposium Series 583; American Chemical Society: Washington, DC
    • (e) Kingston, D. G. I. Recent Advances in the Chemistry and Structure-Activity Relationships of Paclitaxel. In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I., Chen. T. T., Ojima, I., Vyas, D. M., Eds.; ACS Symposium Series 583; American Chemical Society: Washington, DC, 1994; pp 203-216.
    • (1994) Taxane Anticancer Agents: Basic Science and Current Status , pp. 203-216
    • Kingston, D.G.I.1
  • 13
    • 0001843254 scopus 로고
    • History and Chemistry
    • McGuire, W. P., Rowinsky, E. K., Eds.; Marcel Dekker: New York, Basel, Hong Kong
    • (f) Kingston, D. G. I. History and Chemistry. In Paclitaxel in Cancer Treatment; McGuire, W. P., Rowinsky, E. K., Eds.; Marcel Dekker: New York, Basel, Hong Kong, 1995; Vol. 8, pp 1-33.
    • (1995) Paclitaxel in Cancer Treatment , vol.8 , pp. 1-33
    • Kingston, D.G.I.1
  • 15
    • 0025871603 scopus 로고
    • Modified Taxols. 5. Reaction of Taxol with Electrophilic Reagents and Preparation of a Rearranged Taxol Derivative with Tubulin Assembly Activity
    • Samaranayake, G.; Magri, N. F.; Jitrangsri, C.; Kingston, D. G. I. Modified Taxols. 5. Reaction of Taxol with Electrophilic Reagents and Preparation of a Rearranged Taxol Derivative with Tubulin Assembly Activity. J. Org. Chem. 1991, 56, 5114-5119.
    • (1991) J. Org. Chem. , vol.56 , pp. 5114-5119
    • Samaranayake, G.1    Magri, N.F.2    Jitrangsri, C.3    Kingston, D.G.I.4
  • 18
    • 0028080038 scopus 로고
    • 4-Deacetyltaxol and 10-Acetyl-4-deacetyltaxotere: Synthesis and Biological Evaluation
    • Datta, A.; Jayasinghe, L. R.; Georg, G. I. 4-Deacetyltaxol and 10-Acetyl-4-deacetyltaxotere: Synthesis and Biological Evaluation. J. Med. Chem. 1994, 37, 4258-4260.
    • (1994) J. Med. Chem. , vol.37 , pp. 4258-4260
    • Datta, A.1    Jayasinghe, L.R.2    Georg, G.I.3
  • 19
    • 0027946947 scopus 로고
    • First Syntheses of Novel Paclitaxel (Taxol) Analogues Modified at the C4-Position
    • (a) Chen, S.-H.; Kadow, J. F.; Farina, V.; Fairchild, C. R.; Johnston, K. A. First Syntheses of Novel Paclitaxel (Taxol) Analogues Modified at the C4-Position. J. Org. Chem. 1994, 59, 6156-6158.
    • (1994) J. Org. Chem. , vol.59 , pp. 6156-6158
    • Chen, S.-H.1    Kadow, J.F.2    Farina, V.3    Fairchild, C.R.4    Johnston, K.A.5
  • 20
    • 0028997774 scopus 로고
    • Synthesis and Biological Evaluation of Novel C-4 Aziridine Bearing Paclitaxel (Taxol) Analogues
    • (b) Chen, S.-H.; Fairchild, C.; Long, B. H. Synthesis and Biological Evaluation of Novel C-4 Aziridine Bearing Paclitaxel (Taxol) Analogues. J. Med. Chem. 1995, 38, 2263-2267.
    • (1995) J. Med. Chem. , vol.38 , pp. 2263-2267
    • Chen, S.-H.1    Fairchild, C.2    Long, B.H.3
  • 22
    • 0028135187 scopus 로고
    • Selective C-2 and C-4 Deacylation and Acylation of Taxol: The First Synthesis of a C-4 Substituted Taxol Analogue
    • Georg, G. I.; Ali, S. M.; Boge, T. C.; Data, A.; Falborg, L.; Himes, R. H. Selective C-2 and C-4 Deacylation and Acylation of Taxol: The First Synthesis of a C-4 Substituted Taxol Analogue. Tetrahedron Lett. 1994, 35, 8931-8934.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 8931-8934
    • Georg, G.I.1    Ali, S.M.2    Boge, T.C.3    Data, A.4    Falborg, L.5    Himes, R.H.6
  • 24
    • 0028872718 scopus 로고
    • Synthesis of 2-O-Heteroaroyl Taxanes: Evaluation of Microtubule Assembly Promotion and Cytotoxicity
    • (a) Georg, G. L; Harriman, G. C. B.; Ali, S. M.; Datta, A.; Hepperle, M.; Himes, R. H. Synthesis of 2-O-Heteroaroyl Taxanes: Evaluation of Microtubule Assembly Promotion and Cytotoxicity. Bioorg. Med. Chem. Lett. 1995, 5, 115-118.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 115-118
    • Georg, G.L.1    Harriman, G.C.B.2    Ali, S.M.3    Datta, A.4    Hepperle, M.5    Himes, R.H.6
  • 29
    • 0028916505 scopus 로고
    • Differential Effects of Paclitaxel (Taxol) Analogues Modified at Positions C-2, C-7, and C-3′ on Tubulin Polymerization and Polymer Stabilization: Identification of a Hyperactive Paclitaxel Derivative
    • (f) Grover, S.; Rimoldi, J. M.; Molinero, A. A.; Chaudhary, A. G.; Kingston, D. G. I.; Hamel, E. Differential Effects of Paclitaxel (Taxol) Analogues Modified at Positions C-2, C-7, and C-3′ on Tubulin Polymerization and Polymer Stabilization: Identification of a Hyperactive Paclitaxel Derivative. Biochemistry 1995, 34, 3927-3934.
    • (1995) Biochemistry , vol.34 , pp. 3927-3934
    • Grover, S.1    Rimoldi, J.M.2    Molinero, A.A.3    Chaudhary, A.G.4    Kingston, D.G.I.5    Hamel, E.6
  • 30
    • 0027935479 scopus 로고
    • Synthesis and Structure-Activity Relationships of New Antitumor Taxoids. Effects of Cyclohexyl Substitution at the C-3′ and/or C-2 of Taxotere (Docetaxel)
    • (g) Ojima, I.; Duclos, O.; Zucco, M.; Lavelle, F. Synthesis and Structure-Activity Relationships of New Antitumor Taxoids. Effects of Cyclohexyl Substitution at the C-3′ and/or C-2 of Taxotere (Docetaxel). J. Med. Chem. 1994, 37, 2602-2608.
    • (1994) J. Med. Chem. , vol.37 , pp. 2602-2608
    • Ojima, I.1    Duclos, O.2    Zucco, M.3    Lavelle, F.4
  • 32
    • 0031049783 scopus 로고    scopus 로고
    • Syntheses and Structure-Activity Relationships of Nonaromatic Taxoids: Effects of Alkyl and Alkenyl Ester Groups on Cytotoxicity
    • Ojima, I.; Kuduk, S. D.; Pera, P.; Veith, J. M.; Bernacki, R. J. Syntheses and Structure-Activity Relationships of Nonaromatic Taxoids: Effects of Alkyl and Alkenyl Ester Groups on Cytotoxicity. J. Med. Chem. 1997, 40, 279-285.
    • (1997) J. Med. Chem. , vol.40 , pp. 279-285
    • Ojima, I.1    Kuduk, S.D.2    Pera, P.3    Veith, J.M.4    Bernacki, R.J.5
  • 33
    • 0027730478 scopus 로고
    • "Hydrophobie Collapse" of Taxol and Taxotere Solution Conformations in Mixtures of Water and Organic Solvent
    • (a) Vander Velde, D. G.; Georg, G. I.; Grunewald, G. L.; Gunn, C. W.; Mitscher, L. A. "Hydrophobie Collapse" of Taxol and Taxotere Solution Conformations in Mixtures 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
  • 35
    • 0030750497 scopus 로고    scopus 로고
    • A Novel Approach to the Study of Solution Structures and Dynamic Behavior of Paclitaxel and Docetaxel Using Fluorine-Containing Analogues as Probes
    • Ojima, I.; Kuduk, S. D.; Chakravarty, S.; Ourevitch, M.; Bégué, J.-P. A Novel Approach to the Study of Solution Structures and Dynamic Behavior of Paclitaxel and Docetaxel Using Fluorine-Containing Analogues as Probes. J. Am. Chem. Soc. 1997, 119, 5519-5527.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 5519-5527
    • Ojima, I.1    Kuduk, S.D.2    Chakravarty, S.3    Ourevitch, M.4    Bégué, J.-P.5
  • 37
    • 0027252973 scopus 로고
    • Modified Taxols. 8. Deacylation and Reacylation of Baccatin III
    • Samaranayake, G.; Neidigh, K. A.; Kingston, D. G. I. Modified Taxols. 8. Deacylation and Reacylation of Baccatin III. J. Nat. Prod. 1993, 56, 884-898.
    • (1993) J. Nat. Prod. , vol.56 , pp. 884-898
    • Samaranayake, G.1    Neidigh, K.A.2    Kingston, D.G.I.3
  • 38
    • 33845551642 scopus 로고
    • A Mild Two-Step Method for the Hydrolysis/Methanolysis of Secondary Amides and Lactams
    • Flynn, D. L.; Zelle, R. E.; Grieco, P. A. A Mild Two-Step Method for the Hydrolysis/Methanolysis of Secondary Amides and Lactams. J. Org. Chem. 1983, 48, 2424-2426.
    • (1983) J. Org. Chem. , vol.48 , pp. 2424-2426
    • Flynn, D.L.1    Zelle, R.E.2    Grieco, P.A.3
  • 39
    • 0026721268 scopus 로고
    • The Chemistry of Taxanes: Unexpected Rearrangement of Baccatin III during Chemoselective Debenzoylation with Bu3SnOMe/LiCl
    • Farina, V.; Huang, S. The Chemistry of Taxanes: Unexpected Rearrangement of Baccatin III During Chemoselective Debenzoylation with Bu3SnOMe/LiCl. Tetrahedron Lett. 1992, 33, 3979-3982.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3979-3982
    • Farina, V.1    Huang, S.2
  • 41
    • 0026686518 scopus 로고
    • New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogues by means of β-lactam synthon method
    • (b) Ojima, I.; Habus, I.; Zhao, M.; Zucco, M.; Park, Y. H.; Sun, C. M.; Brigaud, T. New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogues by means of β-lactam synthon method. Tetrahedron 1992, 48, 6985-7012.
    • (1992) Tetrahedron , vol.48 , pp. 6985-7012
    • Ojima, I.1    Habus, I.2    Zhao, M.3    Zucco, M.4    Park, Y.H.5    Sun, C.M.6    Brigaud, T.7
  • 42
    • 85127651620 scopus 로고
    • Semisynthesis of Taxol and Taxotere
    • Suffness, M., Ed.; CRC Press: Boca Raton, FL
    • Holton, R. A.; Biediger, R. J.; Boatman, P. D. Semisynthesis of Taxol and Taxotere. In Taxol: Science and Applications; Suffness, M., Ed.; CRC Press: Boca Raton, FL, 1995; pp 97-121.
    • (1995) Taxol: Science and Applications , pp. 97-121
    • Holton, R.A.1    Biediger, R.J.2    Boatman, P.D.3
  • 43
    • 0029968543 scopus 로고    scopus 로고
    • A Convenient Tubulin-Based Quantitative Assay for Paclitaxel (Taxol) Derivatives More Effective in Inducing Assembly than the Parent Compound
    • Lin, C. M.; Jiang, Y. Q.; Chaudhary, A. G.; Rimoldi, J. M.; Kingston, D. G. I.; Hamel, E. A Convenient Tubulin-Based Quantitative Assay for Paclitaxel (Taxol) Derivatives More Effective in Inducing Assembly than the Parent Compound. Cancer Chemother. Pharmacol. 1996, 38, 136-140.
    • (1996) Cancer Chemother. Pharmacol. , vol.38 , pp. 136-140
    • Lin, C.M.1    Jiang, Y.Q.2    Chaudhary, A.G.3    Rimoldi, J.M.4    Kingston, D.G.I.5    Hamel, E.6
  • 44
    • 15144361463 scopus 로고    scopus 로고
    • note
    • 50 is enclosed in quotation marks at its first appearance because taxoids actually enhance tubulin polymerization. In the assay used here, the drug concentration required to reduce the protein in the supernatant by 50% was determined, since the drug-induced polymer is removed from the reaction mixture by centrifugation.
  • 45
    • 0019888672 scopus 로고
    • Interactions of Taxol, Microtubule-Associated Proteins, and Guanine Nucleotides in Tubulin Polymerization
    • Hamel, E.; del Campo, A. A.; Lowe, M. C.; Lin, C. M. Interactions of Taxol, Microtubule-Associated Proteins, and Guanine Nucleotides in Tubulin Polymerization. J. Biol. Chem. 1981, 256, 11887-11894.
    • (1981) J. Biol. Chem. , vol.256 , pp. 11887-11894
    • Hamel, E.1    Del Campo, A.A.2    Lowe, M.C.3    Lin, C.M.4
  • 46
    • 0027323346 scopus 로고
    • Modified Taxols, 9. Synthesis and Biological Evaluation of 7-Substituted Photoaffinity Analogues of Taxol
    • Rimoldi, J. M.; Kingston, D. G. L; Chaudhary, A. K.; Samaranayake, G.; Grover, S.; Hamel, E. Modified Taxols, 9. Synthesis and Biological Evaluation of 7-Substituted Photoaffinity Analogues of Taxol. J. Nat. Prod. 1993, 56, 1313-1330.
    • (1993) J. Nat. Prod. , vol.56 , pp. 1313-1330
    • Rimoldi, J.M.1    Kingston, D.G.L.2    Chaudhary, A.K.3    Samaranayake, G.4    Grover, S.5    Hamel, E.6
  • 48
    • 0030758777 scopus 로고    scopus 로고
    • Paclitaxel resistant human ovarian cancer cells have mutant β-tubulins that exhibit impaired paclitaxel driven polymerization
    • Giannakakou, P.; Sackett, D. L.; Kang, Y.-K.; Zhan, Z.; Buters, J. T. M.; Fojo, T.; Poruchynsky, M. S. Paclitaxel resistant human ovarian cancer cells have mutant β-tubulins that exhibit impaired paclitaxel driven polymerization. J. Biol. Chem. 1997, 272, 17118-17125.
    • (1997) J. Biol. Chem. , vol.272 , pp. 17118-17125
    • Giannakakou, P.1    Sackett, D.L.2    Kang, Y.-K.3    Zhan, Z.4    Buters, J.T.M.5    Fojo, T.6    Poruchynsky, M.S.7
  • 49
    • 0015816824 scopus 로고
    • "Aromatic" Substituent Constants for Structure-Activity Correlations
    • Hansch, C.; Leo, A.; Unger, S. H.; Kim, K. H.; Nikaitani, D.; Lien, E. J. "Aromatic" Substituent Constants for Structure-Activity Correlations. J. Med. Chem. 1973, 16, 1207-1216.
    • (1973) J. Med. Chem. , vol.16 , pp. 1207-1216
    • Hansch, C.1    Leo, A.2    Unger, S.H.3    Kim, K.H.4    Nikaitani, D.5    Lien, E.J.6
  • 50
    • 15144340336 scopus 로고    scopus 로고
    • 50 values greater than 20% are considered significant
    • 50 values greater than 20% are considered significant.
  • 51
    • 0021163546 scopus 로고
    • Separation of Active Tubulin and Microtubule-Associated Proteins by Ultracentrifugation and Isolation of a Component Causing the Formation of Microtubule Bundles
    • Hamel, E.; Lin, C. M. Separation of Active Tubulin and Microtubule-Associated Proteins by Ultracentrifugation and Isolation of a Component Causing the Formation of Microtubule Bundles. Biochemistry 1984, 23, 4173-4184.
    • (1984) Biochemistry , vol.23 , pp. 4173-4184
    • Hamel, E.1    Lin, C.M.2
  • 54
    • 0020009818 scopus 로고
    • Preparation of tubulin from Brain
    • Williams, R. C., Jr.; Lee, J. C. Preparation of tubulin from Brain. Methods Enzymol. 1982, 85, 376-385.
    • (1982) Methods Enzymol. , vol.85 , pp. 376-385
    • Williams Jr., R.C.1    Lee, J.C.2
  • 55
    • 0025827992 scopus 로고
    • Biologically Active Taxol Analogues with Deleted A-Ring Side Chain Substituents and Variable C-2′ Configurations
    • Swindell, C. S.; Krauss, N. E.; Horwitz, S. B.; Ringel, I. Biologically Active Taxol Analogues with Deleted A-Ring Side Chain Substituents and Variable C-2′ Configurations. J. Med. Chem. 1991, 34, 1176-1184.
    • (1991) J. Med. Chem. , vol.34 , pp. 1176-1184
    • Swindell, C.S.1    Krauss, N.E.2    Horwitz, S.B.3    Ringel, I.4


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