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Volumn 39, Issue 5, 2006, Pages 354-361

The phomactins. A novel group of terpenoid platelet activating factor antagonists related biogenetically to the taxanes

Author keywords

[No Author keywords available]

Indexed keywords

BRIDGED COMPOUND; EPOXIDE; FUSED HETEROCYCLIC RINGS; PHOMACTIN A; TAXANE; TAXOID; THROMBOCYTE ACTIVATING FACTOR;

EID: 33745683595     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar050186c     Document Type: Article
Times cited : (60)

References (55)
  • 5
    • 0028788425 scopus 로고
    • Phomactin E, F, and G: New Phomactin-group PAF Antagonists from a Marine Fungus Phoma sp.
    • (d) Sugano, M.; Sato, A.; Iijima, Y.; Furuya, K.; Kuwano, H.; Hata, T. Phomactin E, F, and G: New Phomactin-group PAF Antagonists from a Marine Fungus Phoma sp. J. Antibiot. 1995, 48, 1188-1190.
    • (1995) J. Antibiot. , vol.48 , pp. 1188-1190
    • Sugano, M.1    Sato, A.2    Iijima, Y.3    Furuya, K.4    Kuwano, H.5    Hata, T.6
  • 7
    • 0029979356 scopus 로고    scopus 로고
    • Mechanism of Taxadiene Synthase, a Diterpene Cyclase that Catalyzes the First Step of Taxol Biosynthesis in Pacific Yew
    • (a) Lin, X.; Hezari, M.; Koepp, A. E.; Floss, H. G.; Croteau, R. Mechanism of Taxadiene Synthase, a Diterpene Cyclase that Catalyzes the First Step of Taxol Biosynthesis in Pacific Yew. Biochemistry 1996, 35, 2968-2977.
    • (1996) Biochemistry , vol.35 , pp. 2968-2977
    • Lin, X.1    Hezari, M.2    Koepp, A.E.3    Floss, H.G.4    Croteau, R.5
  • 8
    • 0034523479 scopus 로고    scopus 로고
    • Intramolecular Proton Transfer in the Cyclization of Geranylgeranyl Diphosphate to the Taxadiene Precursor of Taxol Catalyzed by Recombinant Taxadiene Synthase
    • (b) Williams, D. C.; Carroll, B. J.; Jin, Q.; Rithner, C. D.; Lenger, S. R.; Floss, H. G.; Coates, R. M.; Williams, R. M.; Croteau, R. Intramolecular Proton Transfer in the Cyclization of Geranylgeranyl Diphosphate to the Taxadiene Precursor of Taxol Catalyzed by Recombinant Taxadiene Synthase. Chem. Biol. 2000, 7, 969-977.
    • (2000) Chem. Biol. , vol.7 , pp. 969-977
    • Williams, D.C.1    Carroll, B.J.2    Jin, Q.3    Rithner, C.D.4    Lenger, S.R.5    Floss, H.G.6    Coates, R.M.7    Williams, R.M.8    Croteau, R.9
  • 9
    • 28044454336 scopus 로고    scopus 로고
    • Studies on Taxadiene Synthase: Interception of the Cyclisation Cascade at the Isocembrene Stage with GGPP Analogues
    • (c) Chow, S. Y.; Williams, H. J.; Huang, Q.; Nanda, S.; Scott, A. I. Studies on Taxadiene Synthase: Interception of the Cyclisation Cascade at the Isocembrene Stage with GGPP Analogues. J. Org. Chem. 2005, 70, 9997-10003.
    • (2005) J. Org. Chem. , vol.70 , pp. 9997-10003
    • Chow, S.Y.1    Williams, H.J.2    Huang, Q.3    Nanda, S.4    Scott, A.I.5
  • 11
  • 12
    • 0344530815 scopus 로고    scopus 로고
    • Synthetic Studies Towards Congeners of Phomactin A. Reexamination of the Structure of Sch 49028
    • (b) Cheing, J. W. C.; Goldring, W. P. D.; Pattenden, G. Synthetic Studies Towards Congeners of Phomactin A. Reexamination of the Structure of Sch 49028. Chem. Commun. 2003, 2788-2789.
    • (2003) Chem. Commun. , pp. 2788-2789
    • Cheing, J.W.C.1    Goldring, W.P.D.2    Pattenden, G.3
  • 14
    • 1342281362 scopus 로고    scopus 로고
    • Total Synthesis of (±)-Phomactin G, a Platelet Activating Factor Antagonist from the Marine Fungus Phoma sp.
    • (d) Goldring, W. P. D.; Pattenden, G. Total Synthesis of (±)-Phomactin G, a Platelet Activating Factor Antagonist from the Marine Fungus Phoma sp. Org. Biomol. Chem. 2004, 2, 466-473.
    • (2004) Org. Biomol. Chem. , vol.2 , pp. 466-473
    • Goldring, W.P.D.1    Pattenden, G.2
  • 15
    • 0023181459 scopus 로고
    • Perspectives in Platelet-Activating Factor Research
    • Braquet, P.; Touqui, L.; Shen, T. Y.; Vargaftig, B. B. Perspectives in Platelet-Activating Factor Research. Pharm. Rev. 1987, 39, 97-145.
    • (1987) Pharm. Rev. , vol.39 , pp. 97-145
    • Braquet, P.1    Touqui, L.2    Shen, T.Y.3    Vargaftig, B.B.4
  • 18
    • 0014046256 scopus 로고
    • The Ginkgolides
    • (a) Nakanishi, K. The Ginkgolides. Pure Appl. Chem. 1967, 14, 89-113.
    • (1967) Pure Appl. Chem. , vol.14 , pp. 89-113
    • Nakanishi, K.1
  • 19
    • 0003126060 scopus 로고
    • The Ginkgolides, I. Isolation and Characterization of the Various Groups
    • (b) Maruyama, M.; Terahara, A.; Itagaki, Y.; Nakanishi, K. The Ginkgolides, I. Isolation and Characterization of the Various Groups. Tetrahedron Lett. 1967, 8, 299-302.
    • (1967) Tetrahedron Lett. , vol.8 , pp. 299-302
    • Maruyama, M.1    Terahara, A.2    Itagaki, Y.3    Nakanishi, K.4
  • 24
    • 0023212249 scopus 로고
    • The Ginkgolides: Potent Platelet-Activating Factor Antagonists Isolated from Ginkgo biloba L.: Chemistry, Pharmacology and Clinical Applications
    • (g) Braquet, P. The Ginkgolides: Potent Platelet-Activating Factor Antagonists Isolated from Ginkgo biloba L.: Chemistry, Pharmacology and Clinical Applications. Drugs Future 1987, 12, 643-699.
    • (1987) Drugs Future , vol.12 , pp. 643-699
    • Braquet, P.1
  • 25
    • 0008804310 scopus 로고
    • PAF-Acether Specific Binding Sites: 2. Design of Specific Antagonists
    • (h) Braquet, P.; Godfroid, J. J. PAF-Acether Specific Binding Sites: 2. Design of Specific Antagonists. Trends Pharmacol. Sci. 1986, 7, 397-403.
    • (1986) Trends Pharmacol. Sci. , vol.7 , pp. 397-403
    • Braquet, P.1    Godfroid, J.J.2
  • 26
    • 2142696079 scopus 로고
    • PAF Closely Mimics Pathology of Asthma
    • (i) Barnes, P. J.; Chung, K. F. PAF Closely Mimics Pathology of Asthma. Trends Pharmacol. Sci. 1987, 8, 285-287.
    • (1987) Trends Pharmacol. Sci. , vol.8 , pp. 285-287
    • Barnes, P.J.1    Chung, K.F.2
  • 27
    • 49349139162 scopus 로고
    • Structures and Stereochemistry of New Labdane Diterpenoids from Coleus forskohlii briq
    • (a) Bhat, S. V.; Bajwa, B. S.; Dornauer, H.; de Souza, N. J.; Fehlhaber, H.-W. Structures and Stereochemistry of New Labdane Diterpenoids from Coleus forskohlii briq. Tetrahedron Lett. 1977, 18, 1669-1672.
    • (1977) Tetrahedron Lett. , vol.18 , pp. 1669-1672
    • Bhat, S.V.1    Bajwa, B.S.2    Dornauer, H.3    De Souza, N.J.4    Fehlhaber, H.-W.5
  • 28
    • 0342820557 scopus 로고
    • Forskolin and Adenylate Cyclase: New Opportunities in Drug Design
    • (b) Seamon, K. B. Forskolin and Adenylate Cyclase: New Opportunities in Drug Design. Annu. Rep. Med. Chem. 1984, 19, 293-302.
    • (1984) Annu. Rep. Med. Chem. , vol.19 , pp. 293-302
    • Seamon, K.B.1
  • 30
    • 0009645885 scopus 로고
    • Characterization of a Platelet-Activating Factor Receptor Antagonist Isolated from Haifenteng (Piper futokadsura): Specific Inhibition of in Vitro and in Vivo Platelet-Activating Factor-Induced Effects
    • (b) Shen, T. Y.; Hwang, S.-B.; Chang, M. N.; Doebber, T. W.; Lam, M. T.; Wu, M. S.; Wang, X.; Han, G. Q.; Li, R. Z. Characterization of a Platelet-Activating Factor Receptor Antagonist Isolated from Haifenteng (Piper futokadsura): Specific Inhibition of in Vitro and in Vivo Platelet-Activating Factor-Induced Effects. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 672-676.
    • (1985) Proc. Natl. Acad. Sci. U.S.A. , vol.82 , pp. 672-676
    • Shen, T.Y.1    Hwang, S.-B.2    Chang, M.N.3    Doebber, T.W.4    Lam, M.T.5    Wu, M.S.6    Wang, X.7    Han, G.Q.8    Li, R.Z.9
  • 31
    • 3042681488 scopus 로고    scopus 로고
    • Biosynthesis of Phomactins: Common Intermediate Phomactatriene and Taxadiene
    • Tokiwano, T.; Fukushi, E.; Endo T.; Oikawa, H. Biosynthesis of Phomactins: Common Intermediate Phomactatriene and Taxadiene. Chem. Commun. 2004, 1324-1325.
    • (2004) Chem. Commun. , pp. 1324-1325
    • Tokiwano, T.1    Fukushi, E.2    Endo, T.3    Oikawa, H.4
  • 33
    • 0033006040 scopus 로고    scopus 로고
    • Pharmacology of the Eosinophil
    • and references therein
    • Giembycz, M. A.; Lindsay, M. A. Pharmacology of the Eosinophil. Pharm. Rev. 1999, 51, 213-339 and references therein.
    • (1999) Pharm. Rev. , vol.51 , pp. 213-339
    • Giembycz, M.A.1    Lindsay, M.A.2
  • 34
    • 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, 665-666.
    • (1979) Nature , vol.277 , pp. 665-666
    • Schiff, P.B.1    Fant, J.2    Horwitz, S.B.3
  • 35
    • 0030599229 scopus 로고    scopus 로고
    • Total Synthesis of Phomactin D
    • For a synthesis of phomactin D, see: Miyaoka, H.; Saka, Y.; Miura, S.; Yamada, Y. Total Synthesis of Phomactin D. Tetrahedron Lett. 1996, 37, 7107-7110.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7107-7110
    • Miyaoka, H.1    Saka, Y.2    Miura, S.3    Yamada, Y.4
  • 36
    • 0037442639 scopus 로고    scopus 로고
    • Total Synthesis of (+)-Phomactin A Using a B-Alkyl Suzuki Macrocyclization
    • Mohr, P. J.; Halcomb, R. L. Total Synthesis of (+)-Phomactin A Using a B-Alkyl Suzuki Macrocyclization. J. Am. Chem. Soc. 2003, 125, 1712-1713.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 1712-1713
    • Mohr, P.J.1    Halcomb, R.L.2
  • 37
    • 0030032987 scopus 로고    scopus 로고
    • Synthetic Studies Towards Phomactin A. Concise Synthesis of the Novel Tricyclic Furanochroman System
    • Foote, K. M.; Hayes, C. J.; Pattenden, G. Synthetic Studies Towards Phomactin A. Concise Synthesis of the Novel Tricyclic Furanochroman System. Tetrahedron Lett. 1996, 37, 275-278.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 275-278
    • Foote, K.M.1    Hayes, C.J.2    Pattenden, G.3
  • 38
    • 0037062897 scopus 로고    scopus 로고
    • Convergent Enantioselective Synthesis of the Tricyclic Core of Phomactin A
    • Mohr, P. J.; Halcomb, R. L. Convergent Enantioselective Synthesis of the Tricyclic Core of Phomactin A. Org. Lett. 2002, 4, 2413-2416.
    • (2002) Org. Lett. , vol.4 , pp. 2413-2416
    • Mohr, P.J.1    Halcomb, R.L.2
  • 39
    • 0033583017 scopus 로고    scopus 로고
    • Dihydropyrones as Dienophiles in the Diels-Alder Reaction: Application to the Synthesis of 1-Oxadecalones
    • For another approach to the furanochroman core 31, see: (a) Chen, D.; Wang, J.; Totah, N. I. Dihydropyrones as Dienophiles in the Diels-Alder Reaction: Application to the Synthesis of 1-Oxadecalones. J. Org. Chem. 1999, 64, 1776-1777.
    • (1999) J. Org. Chem. , vol.64 , pp. 1776-1777
    • Chen, D.1    Wang, J.2    Totah, N.I.3
  • 40
    • 0033550222 scopus 로고    scopus 로고
    • Synthesis of 1-Oxadecalones via the Lewis Acid-Catalyzed Dihydropyrone Diels-Alder Reaction
    • (b) Seth, P. P.; Totah, N. I. Synthesis of 1-Oxadecalones via the Lewis Acid-Catalyzed Dihydropyrone Diels-Alder Reaction. J. Org. Chem. 1999, 64, 8750-8753.
    • (1999) J. Org. Chem. , vol.64 , pp. 8750-8753
    • Seth, P.P.1    Totah, N.I.2
  • 41
    • 0034704263 scopus 로고    scopus 로고
    • The Dihydropyrone Diels-Alder Reaction: Development and Application to the Synthesis of Highly Functionalized 1-Oxa-4-decalones
    • (c) Seth, P. P.; Chen, D.; Wang, J.; Gao, X.; Totah, N. I. The Dihydropyrone Diels-Alder Reaction: Development and Application to the Synthesis of Highly Functionalized 1-Oxa-4-decalones. Tetrahedron 2000, 56, 10185-10195.
    • (2000) Tetrahedron , vol.56 , pp. 10185-10195
    • Seth, P.P.1    Chen, D.2    Wang, J.3    Gao, X.4    Totah, N.I.5
  • 42
    • 0034632350 scopus 로고    scopus 로고
    • Studies toward the Tricyclic Core of Phomactin A. Synthesis of the Reduced Furanochroman Subunit
    • (d) Seth, P. P.; Totah, N. I. Studies toward the Tricyclic Core of Phomactin A. Synthesis of the Reduced Furanochroman Subunit. Org. Lett. 2000, 2, 2507-2509.
    • (2000) Org. Lett. , vol.2 , pp. 2507-2509
    • Seth, P.P.1    Totah, N.I.2
  • 43
    • 3242710442 scopus 로고    scopus 로고
    • An Approach to the Synthesis of Phomactins Using a Wittig Rearrangement
    • (a) Marsden, A.; Thomas, E. J. An Approach to the Synthesis of Phomactins Using a Wittig Rearrangement. Arkivoc 2002, Part ix, 78-92.
    • (2002) Arkivoc , Issue.9 PART , pp. 78-92
    • Marsden, A.1    Thomas, E.J.2
  • 45
    • 0035905441 scopus 로고    scopus 로고
    • The B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction: Development, Mechanistic Study, and Applications in Natural Product Synthesis
    • For a review that includes the scope for this coupling reaction in synthesis, see: Chemler, S. R.; Trauner, D.; Danishefsky, S. J. The B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction: Development, Mechanistic Study, and Applications in Natural Product Synthesis. Angew. Chem., Int. Ed. 2001, 40, 4544-4568.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 4544-4568
    • Chemler, S.R.1    Trauner, D.2    Danishefsky, S.J.3
  • 46
    • 0037486826 scopus 로고    scopus 로고
    • Carbon-Carbon Bond Formations Involving Organochromium(III) Reagents
    • For a review that includes the scope for this coupling reaction in synthesis, see: Fürstner, A. Carbon-Carbon Bond Formations Involving Organochromium(III) Reagents. Chem. Rev. 1999, 99, 991-1045.
    • (1999) Chem. Rev. , vol.99 , pp. 991-1045
    • Fürstner, A.1
  • 47
    • 0034710507 scopus 로고    scopus 로고
    • Synthesis of the Ring System of Phomactin D Using a Suzuki Macrocyclization
    • Kallan, N. C.; Halcomb, R. L. Synthesis of the Ring System of Phomactin D Using a Suzuki Macrocyclization. Org. Lett. 2000, 2, 2687-2690.
    • (2000) Org. Lett. , vol.2 , pp. 2687-2690
    • Kallan, N.C.1    Halcomb, R.L.2
  • 48
    • 0034710497 scopus 로고    scopus 로고
    • Transannular Macrocyclization via Intramolecular B-Alkyl Suzuki Reaction
    • Chemler, S. R.; Danishefsky, S. J. Transannular Macrocyclization via Intramolecular B-Alkyl Suzuki Reaction. Org. Lett. 2000, 2, 2695-2698.
    • (2000) Org. Lett. , vol.2 , pp. 2695-2698
    • Chemler, S.R.1    Danishefsky, S.J.2
  • 49
    • 0035106991 scopus 로고    scopus 로고
    • Synthesis of the Oxygenated Bicyclo[9.3.1]pentadecane Ring System of Phomactin A Using Chromium (II)-Mediated Macrocyclisation and Ring Closure Metathesis
    • Foote, K. M.; John, M.; Pattenden, G. Synthesis of the Oxygenated Bicyclo[9.3.1]pentadecane Ring System of Phomactin A Using Chromium (II)-Mediated Macrocyclisation and Ring Closure Metathesis. Synlett 2001, 365-368.
    • (2001) Synlett , pp. 365-368
    • Foote, K.M.1    John, M.2    Pattenden, G.3
  • 50
    • 0035902267 scopus 로고    scopus 로고
    • A Nozaki-Hiyama-Kishi Ni(II)/Cr(II) Coupling Approach to the Phomactins
    • Mi, B.; Maleczka, R. E. A Nozaki-Hiyama-Kishi Ni(II)/Cr(II) Coupling Approach to the Phomactins. Org. Lett. 2001, 3, 1491-1494.
    • (2001) Org. Lett. , vol.3 , pp. 1491-1494
    • Mi, B.1    Maleczka, R.E.2
  • 51
    • 0035891621 scopus 로고    scopus 로고
    • Efficient Assembly of the Phomactin Core via Two Different Macrocyclization Protocols
    • Houghton, T. J.; Choi, S.; Rawal, V. H. Efficient Assembly of the Phomactin Core via Two Different Macrocyclization Protocols. Org. Lett. 2001, 3, 3615-3617.
    • (2001) Org. Lett. , vol.3 , pp. 3615-3617
    • Houghton, T.J.1    Choi, S.2    Rawal, V.H.3
  • 52
    • 0345791431 scopus 로고    scopus 로고
    • Intramolecular Formal oxa-[3 + 3] Cycloaddition Approach to the ABD System of Phomactin A
    • Cole, K. P.; Hsung, R. P. Intramolecular Formal oxa-[3 + 3] Cycloaddition Approach to the ABD System of Phomactin A. Org. Lett. 2003, 5, 4843-4846.
    • (2003) Org. Lett. , vol.5 , pp. 4843-4846
    • Cole, K.P.1    Hsung, R.P.2
  • 53
    • 0030459436 scopus 로고    scopus 로고
    • Structure-Activity Relationships of Phomactin Derivatives as Platelet Activating Factor Antagonists
    • Sugano, M.; Sato, A.; Saito, K.; Takaishi, S.; Matsushita, Y.; Iijima, Y. Structure-Activity Relationships of Phomactin Derivatives as Platelet Activating Factor Antagonists. J. Med. Chem. 1996, 39, 5281-5284.
    • (1996) J. Med. Chem. , vol.39 , pp. 5281-5284
    • Sugano, M.1    Sato, A.2    Saito, K.3    Takaishi, S.4    Matsushita, Y.5    Iijima, Y.6
  • 54
    • 0141756322 scopus 로고    scopus 로고
    • Structural Determinants of Blockade of Eosinophil Activation, Adhesion and Secretion by Synthetic Analogues of Phomactin
    • Zhu, X.; Lambertino, A. T.; Houghton, T. J.; McGilvra, J. D.; Xu, C.; Rawal, V. H.; Leff, A. R. Structural Determinants of Blockade of Eosinophil Activation, Adhesion and Secretion by Synthetic Analogues of Phomactin. Life Sci. 2003, 73, 3005-3016.
    • (2003) Life Sci. , vol.73 , pp. 3005-3016
    • Zhu, X.1    Lambertino, A.T.2    Houghton, T.J.3    McGilvra, J.D.4    Xu, C.5    Rawal, V.H.6    Leff, A.R.7


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